The Fingerprints of Intelligence

Lee Harvey Oswald was one of those bright, lost, fatherless boys whom society finds inventive ways of abusing. He never knew his father, Robert, who died of a heart attack before he was born. His mother, Marguerite, suffered from a high-strung disposition and was ill equipped to take care of her three sons. When Lee was three years old, his mother placed him in a New Orleans orphanage known as the Bethlehem Children’s Home, where his two older brothers already resided. Some of the children there fell prey to predatory members of the staff, and Lee was said to have witnessed scenes of sexual exploitation at a tender age. Marguerite withdrew Lee from Bethlehem after a year, and his two brothers came home several months later. But life in the Oswald family continued on a turbulent course, as Marguerite married for a third time and divorced, put her older sons in a Mississippi military school, and moved with Lee to Forth Worth. When Lee’s older brothers fled the domestic chaos and enlisted in the military, he was left adrift with his permanently unsettled mother.

In the summer of 1952, when Lee was nearly thirteen, Marguerite packed up the two of them and headed to New York, where they moved in with her oldest son, John, who was now married and living in an apartment on the Upper East Side. Life was no more stable for Lee in New York, and he often cut class, riding the subways and roaming the streets. Arrested for chronic truancy, Oswald was confined for three weeks in the city’s Youth House for psychiatric evaluation.

Dr. Renatus Hartogs, a German-trained physician who was chief psychiatrist at Youth House, found the intelligent and free-floating Oswald to be such an interesting case that he made the thirteen-year-old the subject of one of his seminars. Hartogs’s psychiatric profile of Oswald—which he would reprise for the Warren Commission a decade later—created the pathological framework by which the alleged assassin would be known for many years to come. Oswald, according to Hartogs, was an “emotionally disturbed, mentally constricted youngster” who was “suspicious and defiant in his attitude toward authority.” While a probation officer had found Lee to be a “small, bright and likable boy” with a reasonable explanation for his truancy—he thought school was “a waste of time” and “the other children made fun of him because of his Texas drawl and his blue jeans”—Hartogs saw Oswald as a walking time bomb. The only reason he had not “acted upon his hostility in an aggressive or destructive fashion” was that he had not yet “developed the courage.”

Hartogs himself was a curious case, one of those intrepid explorers of the human mind who—with government encouragement and funding—had been willing to go to the scientific fringes. His résumé included a stint at Montreal’s Allan Memorial Institute, where Dr. Ewen Cameron conducted his diabolical “Sleep Room” experiments. Hartogs went on to work with Dr. Sidney Malitz of the New York State Psychiatric Institute, which received funding from the Army Chemical Corps and the CIA to conduct drug experiments on unsuspecting patients involving LSD and mescaline. Later, after Hartogs was drummed out of psychiatry by a sensational sex scandal, he turned himself into a hypnosis expert.

Young Oswald had a searching mind. After the teenager was handed a pamphlet on a New York street corner about Julius and Ethel Rosenberg—the spies condemned to death for passing atomic secrets to the Russians—he was moved to learn about Communism, forcing himself to read the heavy Germanic prose of Karl Marx. Oswald dreamed of an exciting world beyond the cramped hysteria of life with Marguerite—where he could make himself into whomever he wanted to be. I Led Three Lives was his favorite TV show—the serial based on the true story of Herbert Philbrick, the mild-mannered Boston advertising executive who had turned himself into an undercover agent for the FBI. The multilayered secrecy of Philbrick’s life resonated with the boy who yearned to escape the drab one-dimensionality of his own. But ignored at home, and left to fend for himself, Lee’s dreams only made him a soft target. As the teenaged Oswald ventured into the world, he was a mooncalf waiting to be exploited.

After returning to New Orleans with his mother in 1954, the fifteen-year-old Oswald hooked up with the Civil Air Patrol, a group of young men interested in learning how to fly. The military auxiliary group, which was founded during World War II to help defend America’s coastlines against German and Japanese attack, not only trained future pilots, it inculcated the patriotic Cold War values of the time. Among its founders was David Harold Byrd, a right-wing Texas oilman and defense contractor. Byrd also owned the Texas School Book Depository, the Dallas warehouse where Oswald would be hired in the fall of 1963 and allegedly establish a sniper’s lair on the sixth floor of the building. It was just one of the many curiosities that marked the life of Lee Harvey Oswald.

In New Orleans, young Oswald’s life began to intersect with older men who saw how he could be of use, including characters who would later have flamboyant walk-on roles in District Attorney Jim Garrison’s valiant but doomed investigation of the Kennedy assassination. David Ferrie—the Eastern Airlines pilot who supervised the local Civil Air Patrol chapter—was a particularly eccentric personality. Suffering from alopecia, Ferrie took to wearing an ill-fitting, reddish wig and filling in his missing eyebrows with theatrical slashes of greasepaint. Catholic-educated and homosexual, he led a secretive and tortured life. He liked to practice hypnosis techniques on the young cadets under his command and tried to lure them into a drug research program at Tulane University with which he was connected. A passionate anti-Communist, Ferrie threw himself into New Orleans’s steamy anti-Castro politics. After the Bay of Pigs debacle, he denounced Kennedy with such vicious abandon during a speech to a veterans group that he was asked to step down from the podium. The president “ought to be shot,” Ferrie began telling people.

In October 1956, Oswald—barely seventeen and less than a month into his tenth grade year—followed the same path as his older brothers, throwing off Marguerite’s “yoke of oppression,” as they put it, and joining the Marines. The following year, he was sent to Atsugi, a naval air base outside of Tokyo, which served as a takeoff point for the CIA’s top secret U-2 spy flights over the Soviet Union. The Atsugi base was also one of the centers for the CIA’s LSD experimentation. A CIA memo titled “‘Truth Drugs’ in Interrogation” revealed the agency practice of dosing agents who were marked for dangerous overseas missions. An operative who had tripped on acid before, the memo noted, would be less likely to crack up if subjected to hallucinogenic treatments by his captors. Some chroniclers of Oswald’s life have suggested that he was one of the young marines on whom the CIA performed its acid tests.

Oswald’s overseas tour of duty was a troubled one. He shot himself in the arm with a derringer, apparently by accident. He was court-martialed twice, once for the illegal possession of a firearm, the second time for pouring a drink over a sergeant in a bar brawl. He suffered a nervous breakdown. But he also continued to be defined by his intelligence and inquisitiveness. He began expressing an interest in traveling to Russia, to see for himself what it was like. In short, he was the sort of boy-man—unfinished, angry, defiant, and hungry to experience life—who stands out from the ranks and gets attention.

At some point, Oswald’s growing curiosity about the Soviet Union—the forbidding land beyond the Iron Curtain that an entire generation of Americans had been taught to fear and hate—began to receive support and guidance. Transferred to El Toro Air Station in Southern California in December 1958, he applied himself to learning Russian, a challenging language difficult to master on one’s own. J. Lee Rankin, the chief counsel for the Warren Commission, would later suggest that Oswald had received training at the Army Language School in Monterey, California, which was known for giving military and intelligence personnel crash courses in a wide range of languages and dialects.

Oswald was now launched on a grand adventure not entirely of his own making. He quit the Marines, claiming—falsely—that his mother was injured and required his help. On September 20, 1959, nine days after receiving his discharge, he set off for Russia, sailing first to England—where he disembarked at Southampton on October 9—and flying to Helsinki shortly thereafter. Oswald later told his wife, Marina, that he had taken a “hop”—a U.S. military transport flight—to get to Finland, which was the easiest point of entry to the Soviet Union.

There was a magical element to Oswald’s journey. Despite the fact that he was a broke ex-serviceman who had only $203 in his bank account when he left America, Oswald enjoyed the best accommodations. In Helsinki, he stayed in two of the city’s finest hotels, the Torni and the Klaus Kurki. After checking out, he still had enough money to buy a ticket on the overnight train to Moscow.

If Oswald was being moved by an unseen hand, his performance at the U.S. embassy in Moscow—where he arrived on a Saturday morning in October to theatrically announce his defection—seemed a particularly awkward piece of staging. There was a scripted quality to the way he renounced his citizenship and declared his intention to turn over military secrets to the Soviets. Listening to the slightly built young man, American consul Richard Snyder had the distinct feeling that “this was part of a scene he had rehearsed before coming into the embassy. It was a preplanned speech.”

But Oswald never seemed certain of the role he was playing during his two and a half years in the Soviet Union. He clearly was not a genuine defector, since the CIA and other U.S. intelligence agencies reacted to his provocative performance at the U.S. embassy with a studied nonchalance, even though he threatened to hand over classified information from his tour of duty at the top secret U-2 base. It took a full year before Angleton’s counterintelligence department finally bothered opening up a standard 201 file on the defector. Oswald did not seem particularly threatening to the Soviets either. While KGB officers found him puzzling, they did not regard him as a master CIA spy. He did not snoop around secure areas. And despite his military service, the Russians learned that he was a bad shot. When Oswald went on expeditions with his factory hunting club in Minsk, he never could hit anything. A co-worker took pity on him once and shot a rabbit for him.

A KGB official described Oswald in one document as “an empty person.” He was the type who could be used as a “dangle” by a sophisticated puppet master like Angleton, someone to flush out moles, to find out what the Soviets knew about the U-2 program. In the Kabuki theater of Angleton’s mind, people played parts whose significance only he understood. It was the paper record—the “legend”—that mattered most to Angleton. Under the covert wizard’s direction, a person’s file sometimes took on a life of its own, full of actions and dialogue that bore no relation to the subject’s real life. To Jim Angleton, the young, pliable American playing the role of defector was a performer who had not yet reached his full potential. He was someone to watch over time.

If there was a real Oswald, the picture emerged in flickering light, only to be seen by the very few people he allowed to get close to him. Nobody was in a better position to observe Lee as he went about his new life in Minsk—where Soviet authorities had given him a sparsely furnished but comfortable apartment and a job in a radio factory—than Ernst Titovets, the medical student who would become Oswald’s best friend in Russia. The two young men spent much of their free time together, pursuing women, playing records in their apartments, going to the opera, and debating the positive and negative aspects of life under capitalism and Communism. Titovets would become Oswald’s Boswell, chronicling the young American’s quotidian life in a revealing memoir that would be published in Russia a half century later, but remain largely unknown in the United States.

Titovets was better educated and more culturally sophisticated than his American friend. The Russian had to explain to Oswald who George Gershwin was. But in spite of the high school dropout’s education gaps, Titovets recognized that Oswald was an innately smart young man. “I had ample opportunity to observe during our debates how quick he was to grasp the essence of an abstract philosophical idea,” Titovets later wrote in his memoir. “I carried away an impression of him as a very intelligent, quick-witted person.”

Oswald, whose childhood hardships had made him sensitive to the exploitation of the poor and weak, was drawn to Marxism’s egalitarian promise and seemed genuinely intrigued by the Soviet system. But, American to the core, he soon began to chafe under the regimentation of life in Minsk, making fun of the omnipresent Lenin posters that loomed over his radio factory and grumbling about the compulsory exercise sessions and propaganda meetings in which workers had to participate. He once staged a one-man strike to protest what he said were the factory’s outdated work practices. Work life in the United States was no paradise, Oswald acknowledged to Titovets, and racism was a national disgrace. But all in all, American workers enjoyed a higher standard of living and more freedom, he said. “You live like slaves!” Oswald once yelled during a particularly heated discussion with his Russian friend.

On the whole, Oswald did not strike Titovets as being the political extremist that he was widely portrayed to be after the Kennedy assassination. “Oswald did not produce the impression of a narrow-minded political zealot . . . nor would he push his ideas on others. A good listener, he was ready to learn new things and kept his mind open to new ideas.” Titovets saw his American companion as a work in progress, someone trying to bridge the chasm between East and West, and develop his own political philosophy. As he prepared to return to America, Oswald began drafting his vision of the ideal society, one that combined the best features of capitalism and socialism, which he called the “Athenian system.” One biographer would later describe Oswald as a “pioneer . . . a lonely American anti-hero a few years ahead of his time,” working out his social theories thousands of miles away from home—ideas that mirrored the grassroots, participatory democracy that would soon be advocated by the New Left.

Nothing about the Oswald that Titovets knew conformed to the profile of the angry loner in the Warren Report. He was popular with women and he had an easy way with children. When tense confrontations arose with other men—like the time he got into an argument with a fellow worker named Max over a shop machine—Oswald seemed to go limp. Even after Max grabbed a fistful of his shirt and shoved him against a steel pillar, Oswald simply stood quietly contemplating his antagonist until the man’s rage spent itself. “Judging by what I learned about Oswald,” concluded Titovets, who studied psychiatry in medical school, “it would have been a psychological impossibility for him to kill a man.”

While living in Minsk, Oswald displayed a sharp awareness of Soviet surveillance that seemed to indicate some prior training. Oswald kept his apartment in spartan condition, as if carefully refraining from giving his living quarters any identifying characteristics. He would painstakingly examine his room for KGB bugs, and play his record player loud during some conversations to frustrate any eavesdroppers. Visiting his apartment always gave Titovets a vaguely uneasy feeling. “I wondered what particular feature about the room generated that uncanny feeling of loneliness mixed with an unreasonable, animal-like feeling of being constantly watched. Nice to discover a sort of creeping paranoia coming over you!”

As when he was a boy, Oswald continued to be interested in the make-believe world of spies. Perusing Titovets’s collection of English-language books one day, he chose to borrow The Quiet American, Graham Greene’s mordant tale of a U.S. agent in French colonial Vietnam who wreaks havoc through his shiny idealism. Nonetheless, Titovets doubted that Oswald was an American spy. He seemed to show no interest in intelligence gathering during his years in Russia. And there was no evidence that he was turned by the KGB. “Oswald maintained his allegiance to his native country throughout his Russian period,” Titovets later wrote. “His loyalty was evident in small gestures he made rather than in flashy bombastic pronouncements. He was proud of his service with the U.S. Marines. Whenever we compared Russia with the United States, he invariably defended the American side. . . . He would defend the American Army, American English, American girls, American food and American ways—you name it.”

But if Oswald was not acting as a paid operative, he was being acted upon. By early 1961, when Oswald notified the U.S. embassy in Moscow that he wanted to return to America, he was the subject of an enormous amount of secret paperwork in the deep recesses of the CIA, FBI, State Department, and Office of Naval Intelligence.

Years later, Richard Schweiker—the Republican senator from Pennsylvania who was one of the first legislators to try to unravel the mystery of Lee Harvey Oswald, while serving with the Church Committee—eloquently summed up the strange malleability of Oswald’s life. “Everywhere you look with him,” said Schweiker, “there are the fingerprints of intelligence.”

Oswald’s reentry into the United States was absurdly easy, considering his treasonous track record. He had tried to renounce his citizenship; he had declared his intention to betray his country by handing over some of its most zealously guarded military secrets; he had lived as if he were a Soviet citizen for well over two years. And to top it off, he was bringing back with him a Russian wife, Marina, who had been raised by an uncle who was a KGB officer.

Titovets had taken an immediate disliking to Marina, whom he regarded as a chain-smoking, foulmouthed woman with none of Oswald’s intellectual complexity. But Oswald immediately fell under the spell of the sad-eyed beauty with sensuous lips. “The girl emanated raw sexuality about her, repellent to me, but perhaps precisely the feature that attracted Lee,” observed Titovets. Lee and Marina were introduced at a dance at the Trade Union House, one of Minsk’s popular entertainment centers. “The low cut of her dress stressed the size of her breasts,” Titovets recalled. He immediately suspected she was KGB bait for Oswald. When he later asked around about Marina, Titovets was told that she had been run out of Leningrad by local authorities. “Taking into account her past history and her legal problems,” he concluded, “she certainly had given the KGB a sure hold over her.” A month after he met Marina, Oswald proposed to her.

It was one more curious episode in Oswald’s life. And yet none of his suspicious past, or that of his bride, caused U.S. authorities to block his return, place him under detention, or subject him to rigorous interrogation. At the height of the Cold War—when paranoia about spies, subversives, and “brainwashed” GIs ran rampant throughout America—Oswald and his Soviet wife were allowed to pass smoothly into the country. The State Department even provided a $435 loan to help pay for the couple’s travel expenses. When the SS Maasdam, the cruise liner from Rotterdam carrying the Oswalds and their infant daughter, docked at a Hoboken pier on the rainy afternoon of June 13, 1962, there were no federal agents awaiting the defector.

The Oswalds were greeted only by a Travelers Aid Society caseworker named Spas Raikin. Despite persistent rumors, Raikin has always vehemently denied that he was working for the CIA. But Raikin—a Bulgarian refugee who was active in anti-Communist politics—was politically sophisticated enough to realize that there was something strange about Oswald’s uneventful return to the United States. It was one more instance, in Oswald’s endlessly mystifying life, when the dog did not bark. “I wondered why there weren’t any government officials to meet him,” Raikin recalled late in his life. “In my mind, there was the idea he could be a spy. . . . I had suspicion, but I did not want to get further involved into this thing.”

The day after arriving in the United States, the Oswalds flew to Fort Worth, where they moved in temporarily with Lee’s brother, Robert. It would take nearly two weeks before the FBI got around to interviewing Lee.

Oswald was now entering the final act of his abbreviated life. Over the next year and a half, the young man seemed to lead an aimless existence, drifting to New Orleans, returning to Texas, taking a side trip to Mexico City, as he jumped from one job to the next, before finally ending up in the Texas School Book Depository. But on closer examination, there was a method to his movements. While in Texas, Oswald and his family came under the watchful care of people who in turn were being closely watched. He met quietly with a prominent CIA officer in Dallas. He staged public scenes in New Orleans and Mexico City that called attention to himself as a hotheaded militant, as he had done at the embassy in Moscow. There were invisible wires attached to Oswald—and some of the more intriguing ones led to Allen Dulles.

Lee Harvey Oswald was given to grand daydreams. He had big ideas about how to change the world; he wanted to be part of a larger mission than his petty circumstances allowed. But there were others who had their own plans for him. “[Lee] did not know who he was really serving,” Marina said years later. “He was manipulated and he got caught. He tried to play with the big boys.”

George de Mohrenschildt dropped into the Oswalds’ threadbare lives in Fort Worth like a beneficent fairy-tale prince. Tall, well groomed, cosmopolitan, with a network of high-placed friends that stretched from Dallas oil society to the European aristocracy, “Baron” de Mohrenschildt—as he enjoyed being called—was everything Oswald was not. He showed up one afternoon on the doorstep of the Oswalds’ humble home—which he later described as “a shack near Sears Roebuck, as far as I remember . . . very poorly furnished, decrepit, on a dusty road.” He was there, he said, on a mission of mercy—a White Russian émigré of noble birth who had done well for himself in America, lending a hand to an impoverished young couple recently arrived from his native land. De Mohrenschildt, a decadent old-world roué when it came to women, did not think much of Marina when he met her that day, finding her “not particularly pretty” and “a lost soul.” But he immediately took a liking to Oswald, whom he found “charming.”

Over the following months, de Mohrenschildt and his equally sophisticated wife, Jeanne—a fellow high-born Russian whose father had run the Far Eastern Railroad in China—hovered over the Oswalds, finding Lee jobs, installing the family in new living quarters, making sure that Marina’s rotting teeth were fixed and their baby got her inoculations, taking the young couple to parties, and intervening in their quarrels when they became violent. Later, when people remarked on how unlikely the friendship between the sophisticated baron and the high school dropout was, de Mohrenschildt simply shrugged it off. “I believe it is a privilege of an older age not to give a damn what others think of you. I choose my friends just because they appeal to me. And Lee did.”

De Mohrenschildt explained that he admired his young friend’s rejection of the segregationist values of his native South, as well as Oswald’s complete disinterest in the rampant materialism of American life—unlike Marina, whom the baron found crude and moneygrubbing. “I am not a turkey which lives only to become fat,” Oswald announced with a smile one day, lifting his shirt to show de Mohrenschildt his minimal belly. “Lee, your way of life is so un-American, it scares me to think what may become of you,” the older man responded.

There was another reason he was drawn to Oswald, de Mohrenschildt later said. The scrawny young man with the big ideas about life reminded him of his only son, Sergei, who had died of cystic fibrosis a year earlier. Sweeping into Oswald’s life when he was still grieving the loss of Sergei, de Mohrenschildt came to think of Lee as “almost a son.”

But there were less sentimental reasons why the baron befriended the wayward young American. De Mohrenschildt was minding the Oswalds for the CIA.

George de Mohrenschildt came from that lost world of Russian cavalry officers and palace balls that had been vaporized by war and revolution. His father, Sergius, had been a czarist official and a director of Nobel Oil, the petroleum giant that struck fortune in the abundant Baku fields. When the Bolsheviks took power, Sergius was arrested and sentenced to a Siberian work camp, but the family fled to Poland. The de Mohrenschildts lost most of their old lives in exodus—including their land and their position, as well as George’s mother, who succumbed to typhoid fever. The surviving members of the family—especially Sergius and George’s older brother, Dimitri—developed a burning anti-Communist rage. His father “hated communism,” George later said. “That was his life’s hatred.”

During World War II, as Poland became a “blood land” in the fighting between Hitler’s Wehrmacht and Stalin’s Red Army, Sergius fled west again, to Nazi Germany, where he was welcomed as a comrade in the war to the finish with Asiatic Bolshevism. Sergius was not a devoted Nazi, but he soon acclimated himself to his new fatherland, doing work for the Abwehr, the German military intelligence agency. “George,” he told his son, “the Nazis are no good, and Germany is going to lose the war, but I prefer to be in Germany than in Soviet Russia. At least I am free and nobody is bothering me.” But history finally caught up with Sergius—he was killed near the end of the war during an Allied bombing raid.

Meanwhile, Dimitri von Mohrenschildt (George’s brother preferred the German version of the family name) emigrated to America, where he would prosper—one of the cultured White Russians who managed to work their way into East Coast high society. Dimitri married Winifred “Betty” Hooker, a divorced Park Avenue socialite, and became a prominent scholar, winning appointment in 1950 as the first chairman of Dartmouth’s Russian Civilization Department and launching the Russian Review, an anti-Communist journal. Dimitri moved in those circles where millionaires, academics, and spies commingled. He and his wife counted the Bouviers—the parents of future First Lady Jackie Kennedy—as well as the dynastic Bush family among their friends. Dimitri’s coeditor at theRussian Review—the conservative author William Henry Chamberlin—was a friend of Allen Dulles’s, with whom he worked on the Radio Liberty Committee, one of the Cold War propaganda projects launched by Dulles and his associates in the postwar period. Dimitri himself became a CIA asset in April 1950, when, according to an agency memo, he was approved as a contact for foreign intelligence purposes.

Dimitri had brought his younger brother to America in 1938. George—who stayed for a time with Dimitri and his wife in their Park Avenue apartment and Long Island estate—envied their good life, but seemed uncertain how to achieve it for himself. George lacked his brother’s strong political convictions—veering between Nazi and Communist sympathies early in his life, and later between an aristocratic paternalism and a sentimental New Leftism. George was also missing Dimitri’s professional discipline and sense of direction. After arriving in America, George tried his hand at selling sports clothes with his girlfriend at the time, and when that venture flopped, he briefly became a perfume salesman. Later, he gave the insurance business a shot but failed to sell a single policy.

Finally, George de Mohrenschildt settled on the oil business, figuring that he would follow in his father’s footsteps. He eventually wound up in Texas, where he got a petroleum geology degree from the University of Texas, after cheating his way through the final exams. In typical de Mohrenschildt style, he charmed his way out of trouble when he got caught, explaining with an aristocratic wink that everyone in life cheats.

De Mohrenschildt—who sported the year-round tan of a yachtsman or skier—continued to rely on his good looks and old-world charm as he pursued his career in the oil business. He had a gift for bedding and wedding wealthy women—including an eighteen-year-old Palm Beach debutante—and then tapping their families for funds to launch his various oil ventures. The second of his four wives, Phyllis, was “a little bit wild—but very attractive and adventurous,” the baron told the Warren Commission. She was in the habit of walking around the rugged oil field in the Colorado Rockies where de Mohrenschildt was working at the time, wearing only a bikini—a new fashion item in those days that the roughnecks working their drills undoubtedly found intriguing.

Albert Jenner Jr., the Warren Commission co-counsel in charge of questioning de Mohrenschildt, displayed a keen interest in his active love life. The baron conceded that he was something of a ladies’ man. “I am not a queer, you know,” he testified. “Although some people accuse me of that even.” While he knew how to seduce women, de Mohrenschildt could also be cruel to them. Dorothy, his teenaged bride, later said that he manhandled her, once kicking her in the stomach and striking her on the head with a hammer. He also enjoyed “kissing and pawing other women” right in front of her. The baron’s sexual habits were “abnormal,” declared Dorothy as she fled the marriage.

None of de Mohrenschildt’s oil ventures paid off particularly well, and he would soon drift away to try one more roll of the dice with the help of another rich relative or friend. His true skill was cultivating the wealthy and well connected. One of his first jobs in the oil business was working for Pantepec Oil—the petroleum company founded by the father of William F. Buckley Jr., the CIA-connected conservative publisher and pundit.

Later, de Mohrenschildt proved adept at working his connections at the Dallas Petroleum Club, a hotbed of anti-Kennedy ferment, whose leading members—including oilmen Clint Murchison Sr., H. L. Hunt, and Sid Richardson—were tied to Dulles, Lyndon Johnson, and J. Edgar Hoover. The Petroleum Club also counted D. H. Byrd, the Texas School Book Depository owner, and Mayor Earle Cabell, brother of Dulles’s former CIA deputy, among its regulars. De Mohrenschildt put Byrd’s wife on the board of the charity that he had set up to fund cystic fibrosis research. It all came together at the Petroleum Club—the deals, the good works, and the darker stuff—over drinks in the club’s wood-paneled rooms, located downtown in the elegant Baker Hotel.

The international oil business and the U.S. intelligence establishment were overlapping worlds, and de Mohrenschildt soon found himself with a foot in each one. He alluded cryptically to this early in his Warren Commission testimony, when he mentioned that he was involved in “a controversial business . . . international business.” But commission attorney Jenner quickly steered the conversation away from these dangerous shoals. “Also, I gather that you are a pretty lively character,” Jenner interjected inanely.

De Mohrenschildt was indeed a colorful character, as Jenner observed more than once during the hearing. But this was a less relevant aspect of the baron’s life than his involvement with American espionage. In the late 1950s, de Mohrenschildt stopped drilling dry wells in Texas and Colorado and started spending more time overseas, as a consultant on petroleum projects in Latin America, Europe, and Africa. His work sometimes took him to Cold War hot spots such as Yugoslavia (which ejected him as a suspected spy) and Cuba. When he returned from his trips abroad, de Mohrenschildt was routinely debriefed by the CIA’s Dallas field agent, J. Walton Moore.

The baron always insisted that he was not a CIA agent, though his denials could sometimes be convoluted. “I cannot say that I never was a CIA agent, I cannot prove it,” he wrote near the end of his life, in an unpublished memoir. “I cannot prove either that I ever was. Nobody can.” While it was probably true that de Mohrenschildt was not an official agent, he was most certainly an agency asset, gathering confidential information on his foreign business trips under what the CIA called “commercial cover.”

De Mohrenschildt was not motivated by ideology or patriotism. He was not like his brother, whom he described almost bemusedly as “really a ferocious anti-communist.” The baron did “not believe in anything, either religious or political,” said his Dallas neighbor, a fellow White Russian named Igor Voshinin. De Mohrenschildt believed only in himself. He had learned from his rootless, stateless existence to ingratiate himself with whomever had power or money. He was at your service, if he could also serve himself. He wasn’t much of an oilman, but having friends in the spy world opened doors for him when doing business overseas.

So it was not surprising when de Mohrenschildt showed up at the Oswalds’ front door that summer afternoon in the company of a man named Colonel Lawrence Orlov, a CIA informant who was a friend and frequent handball partner of J. Walton Moore, the agency’s man in Dallas. De Mohrenschildt himself had also become friendly with Moore, when the CIA “domestic contacts” agent began debriefing him after his overseas trips. The baron thought of his CIA handler as a “very nice fellow . . . and we got along well.” Moore, the son of missionary parents, had been born and raised in China, like de Mohrenschildt’s wife, Jeanne. “So I invited him and his wife to the house and he got along fabulously well with Jeanne,” the baron later recalled. “I used to see Mr. Moore occasionally for lunch. A cosmopolitan character, most attractive.”

After the Oswalds arrived in Texas from Russia, it was Moore’s turn to invite de Mohrenschildt to lunch. The CIA man had a request for his Russian-born friend. De Mohrenschildt was apparently tasked with keeping an eye on the young couple—a job he assiduously performed until the following spring, when he and his wife left on business for Haiti.

Lee was in thrall to de Mohrenschildt, the big, suave man of the world—the father figure he never had. They swapped political jokes from either side of the Iron Curtain. The baron grilled him about his life in Minsk, as if he were conducting an agency debriefing. But Lee didn’t seem to mind—he glowed under the older man’s attention. “Oswald would do anything that de Mohrenschildt told him to do,” observed the baron’s son-in-law, Gary Taylor, who lived in Dallas with de Mohrenschildt’s daughter, Alexandra.

Marina Oswald later agreed that de Mohrenschildt and her husband had been “fairly good friends” and that the baron was “a good humanitarian who was interested in other people.” But in an interview with FBI agents after the assassination, Marina added a provocative remark about the two men’s relationship. Oswald “was somewhat afraid of de Mohrenschildt, who was big in stature and talked loudly,” she reported. Her husband clearly knew who, between the two of them, had the power.

In the end, no Warren Commission witness betrayed Oswald more deeply than George de Mohrenschildt. His testimony before the commission—the lengthiest of the hearings—did more to convict Oswald in the eyes of the press and the public than anyone else. He tied Oswald to the alleged murder weapon, telling the commission about the day when an agitated Marina showed him and his wife the rifle that Lee had stashed in a closet. And most important, de Mohrenschildt gave the Warren Commission the motive for killing Kennedy that the panel had sorely lacked. Oswald, the baron speculated with devastating effect, “was insanely jealous of an extraordinarily successful man, who was young, attractive, had a beautiful wife, had all the money in the world, and was a world figure. And poor Oswald was just the opposite. He had nothing. He had a bitchy wife, had no money, was a miserable failure in everything he did.” Shooting Kennedy, he concluded in one of the more memorable phrases produced by the official investigation, made Oswald “a hero in his own mind.”

De Mohrenschildt had enough of a conscience to feel uneasy about his Judas-like performance before the commission, and—as if to make amends—he offered contradictory testimony about Oswald. “But what I wanted to underline, that was always amazing to me, that as far as I am concerned [Oswald] was an admirer of President Kennedy,” he told the panel. During a conversation they had about JFK, acknowledged de Mohrenschildt, Oswald described him as “an excellent president, young, full of energy, full of good ideas.” Oswald’s own words about Kennedy completely erased the motive that de Mohrenschildt proposed to the panel. But the Warren Commission simply glided over the glaring inconsistencies in de Mohrenschildt’s testimony. It was the baron’s unfounded and irresponsible remarks about the “crazy lunatic” Oswald—a man supposedly driven to kill by the resentments born of his pathetic life—that stuck with the commission. De Mohrenschildt took the young man with whom he had spent hours discussing politics and offering advice about love and marriage—the man who hung on his every word, whom he thought of as a son—and threw him under the wheels of infamy.

On the morning of April 22, 1964, when he appeared at the Veterans Administration building in Washington—where the Warren Commission had set up shop—George de Mohrenschildt was not in possession of his customary smooth, self-composed demeanor. The months after the assassination had been extremely difficult ones for the baron and his wife. He had been summoned to the U.S. embassy in Port-au-Prince and treated like he was a suspect in the case. His business affairs in Haiti began to suffer as rumors spread about the mysterious Russian who had been Oswald’s closest confidant. It is highly unlikely that de Mohrenschildt knew in advance about how Oswald was to be used on November 22, 1963. This sort of messy business was not part of the baron’s portfolio. But he was sharp enough to quickly begin connecting the dots.

De Mohrenschildt was not certain how he would come out of the Warren Commission hearings. Would his career be ruined? Would he be put on trial? Or did he face even more dire consequences? America was not Soviet Russia, but the baron had learned from his worldwide wanderings that power was capable of anything, no matter where it operated.

De Mohrenschildt was quite anxious when he entered the hearing room that morning. His eyes fixed immediately on Allen Dulles. The spymaster “did not interfere in the proceedings” that day, observed de Mohrenschildt, letting Jenner handle the interrogation. But the baron found Dulles’s silent presence to be unnerving. “[He] was there as a distant threat,” de Mohrenschildt later wrote in his memoir—a provocative remark that he did not explain further. Was the mere presence of Dulles, looming over the proceedings, a reminder that de Mohrenschildt must carefully mind his words?

The baron found his entire experience as a star witness for the Warren Commission—which dragged on for two days—to be a grueling exercise in “intimidation.” As he prepared to begin his testimony, de Mohrenschildt later claimed, Jenner put him on stern notice. “We know more about your life than you yourself, so answer all my questions truthful[ly] and sincerely,” Jenner warned him. Over the next two days, Jenner switched between chilly aggressiveness and ingratiating flattery as he worked over de Mohrenschildt. Afterward, Jeanne de Mohrenschildt followed her husband to the witness table, bringing along their two Manchester terriers, Nero and Poppaea, for emotional support. When the de Mohrenschildts’ interrogation was all over, the baron told his wife, “It was an unpleasant experience, but in Russia we would have been sent to Siberia for life.”

Jenner raked over the most embarrassing details of de Mohrenschildt’s private life, but he stayed resolutely clear of his espionage connections. The baron realized just how thoroughly the commission had penetrated his personal life when Dulles got his hands on private correspondence that de Mohrenschildt had exchanged with the First Lady’s mother, Janet, following the Kennedy assassination. After divorcing Jackie’s rakish father, “Black Jack” Bouvier, Janet had married Washington stockbroker Hugh Auchincloss, whose family fortune derived from his grandfather’s Standard Oil partnership with John D. Rockefeller. De Mohrenschildt was forced by the Warren Commission to read out loud from his own letters to Janet Auchincloss, whom he had known from the time that her daughter Jackie was a girl, romping on the sands of Long Island’s Gold Coast. Jenner put the baron on the spot, asking him to explain why he had questioned Oswald’s guilt in one letter he sent Jackie Kennedy’s mother. “Somehow,” he wrote Mrs. Auchincloss three weeks after the assassination, “I still have a lingering doubt, notwithstanding all the evidence, of Oswald’s guilt.” Since his letter obviously undermined his own testimony about Oswald as the “crazy lunatic” who killed the president, de Mohrenschildt was put in the awkward position of trying to clarify his contradictory remarks.

After the de Mohrenschildts concluded their Warren Commission “ordeal,” they were invited by Janet Auchincloss and her husband to their home on O Street in Georgetown. Relaxing with his old friend in the comfortable splendor of her home, the baron and his wife felt confident enough to voice their true feelings about the assassination. By now, it was dawning on the couple that the Warren Commission was not interested in the real story of the president’s murder. They suspected that the true purpose of the investigation was “to waste the taxpayers’ money and to distract [the] attention of the American people from the [real culprits] involved in the assassination.”

Jeanne de Mohrenschildt risked upsetting the civility of the gathering by directly challenging Mrs. Auchincloss. “Why don’t you—the relatives of our beloved president, you who are so wealthy—why don’t you conduct a real investigation as to who was the rat who killed him?”

Mrs. Auchincloss regarded Jeanne coldly. “But the rat was your friend Lee Harvey Oswald.” She was in no mood to be lectured by friends of Oswald. Upstairs in her attic, Mrs. Auchincloss was still keeping the blood-spattered pink Chanel suit that her daughter had worn in Dallas.

Jackie Kennedy’s mother had no doubt arrived at her conviction about Oswald’s guilt with the help of her neighbor and family friend, Allen Dulles. Her husband, Hugh—who had served in Navy intelligence before pursuing his investment banking career—and Dulles were from the same world. The Auchinclosses, in fact, had more in common politically with Dulles than they did with the late president. When de Mohrenschildt had bumped into JFK’s mother-in-law on a plane trip during the 1960 campaign, he was surprised to hear Mrs. Auchincloss tell him that she was a staunch Nixon supporter and that Jack did not stand a chance.

It was a remarkable scene at the Auchincloss mansion that spring evening in 1964. Fresh from their cowardly performance before the Warren Commission, the de Mohrenschildts were now urging JFK’s in-laws, who had never supported him politically, to show some moral courage and use their wealth to solve the crime. Despite how his wife had been rebuffed, de Mohrenschildt continued to argue the point with Mrs. Auchincloss. “Janet, you were Jack Kennedy’s mother-in-law, and I am a complete stranger. But I would spend my own money and lots of time to find out who were the real assassins or the conspirators. Don’t you want any further investigation? You have infinite resources.”

But Mrs. Auchincloss was unmoved. “Jack is dead and nothing will bring him back.” Finally, as the discussion reached an emotional crescendo, the two women—Janet and Jeanne—fell into each other’s arms and began weeping.

As if the evening were not unsettling enough, at some point Dulles himself showed up. The spymaster circled in on de Mohrenschildt and began asking him pointed questions about Oswald, as if they were still in the hearing room. Did the accused assassin have any reason to hate Kennedy? The “astute” Dulles, as the baron described him, knew that this was the most mixed-up part of de Mohrenschildt’s testimony and it was imperative to “fix” it, if the commission were to succeed in portraying Oswald as a lone nut. But de Mohrenschildt again frustrated Dulles, giving him the answer Dulles did not want to hear. No, he said, Oswald did not hate Kennedy—in fact, he was “an admirer” of the president. At this point, Dulles would have certainly noted that—despite his accommodating performance before the Warren inquiry—George de Mohrenschildt might pose a problem further down the line.

Later that evening, as the de Mohrenschildts took their leave, Janet Auchincloss took the baron aside. “Incidentally,” she said in a voice now tinged with frost, “my daughter Jacqueline never wants to see you again because you were close to her husband’s assassin.”

“It’s her privilege,” was the baron’s courtly reply.

It was the beginning of another kind of exile for the rootless cosmopolite, who would find himself increasingly banished from the high society world that he depended on for contacts and contracts. It all seemed grossly unfair to the baron. His only sin had been to believe his CIA friend Moore when Moore told him that Oswald was merely a “harmless” eccentric who needed some friendly supervision. De Mohrenschildt prided himself on his worldliness. But in the end, he realized, he had been used—just like Oswald, who, after being taken into police custody, had shouted out frantically that he was “a patsy.” De Mohrenschildt, too, had been set up to play a role—to incriminate Oswald. And, like Oswald, he didn’t realize it until it was too late.

In the last years of his life, de Mohrenschildt sought atonement for his sins, to make it right with the ghost of Lee Harvey Oswald. In his memoir, I Am a Patsy!—an outpouring from the heart whose raw, Russian-accented syntax de Mohrenschildt did not bother to polish—he apologized for the “damage” he had caused “to the memory of Lee, my dear friend.” He proclaimed Oswald’s innocence and took back the damning things he had told the Warren Commission. In truth, “Lee was not jealous of [the] Kennedys’ wealth,” he wrote, “and did not envy their social positions, of that I was sure. To him wealth and society were big jokes, but he did not resent them.”

De Mohrenschildt had described Oswald to the Warren Commission as a “semi-educated hillbilly”—someone “you can’t take seriously . . . you just laugh at.” But now, he wrote of his late friend’s “original mind” and his “nonconformist” thinking. Along with the Titovets chronicle, I Am a Patsy! stands out as the most convincing portrait we have of the true Oswald. De Mohrenschildt’s manuscript, which his wife gave to the House Select Committee on Assassinations after his death, remains unpublished but is available online.

Oswald comes across in the baron’s memoir as a budding ’60s radical—a man sensitive enough to identify with the plight of black Americans and Native Americans in a white-dominated society, and hardheaded enough to recognize the fundamental flaws of American democracy. “Under dictatorship, people are enslaved but they know it,” he told de Mohrenschildt, recalling his days in the Soviet Union. “Here, the politicians constantly lie to people and they become immune to these lies because they have the privilege of voting. But voting is rigged and democracy here is a gigantic profusion of lies and clever brainwashing.” Oswald worried about the FBI’s police-state surveillance tactics. And he believed that America was turning more “militaristic” as it increasingly interfered in the internal affairs of other countries. Someday, he predicted, there would be a coup d’état.

As de Mohrenschildt contemplated America in the mid-1970s, when he wrote his manuscript, he began to regard Oswald as a prophetic figure. By then, the United States was a country debased by war, assassination, government corruption, and constitutional subversion. “My wife and I spent many an agonizing moment thinking of Lee, ashamed that we did not stand up more decisively in his defense,” he wrote. “But who would have listened to us at the time and would have published anything true and favorable [about] him?”

De Mohrenschildt’s life took on a frantic quality near the end, as he began working on his memoir and trying to make sense of his entangled relationship with Oswald. In September 1976, he mailed a distraught, handwritten letter to his old family friend, George Bush, who was then serving as CIA director in the Gerald Ford administration. De Mohrenschildt knew Bush from his prep school days at Phillips Academy, when Bush was the roommate of Dimitri von Mohrenschildt’s stepson. Now the baron was appealing to the CIA director’s sense of family and class loyalty to help him. De Mohrenschildt claimed that he and his wife were the targets of some sort of harassment. “Our phone [is] bugged, and we are being followed everywhere. . . . We are being driven to insanity by the situation.” De Mohrenschildt thought the surveillance campaign began after he suffered the death of a second child from cystic fibrosis—his daughter Nadya—a traumatic event that had made him start “behaving like a damn fool” and delving into his painful past. He began “to write, stupidly and unsuccessfully, about Lee H. Oswald,” de Mohrenschildt told Bush, “and [I] must have angered a lot of people I do not know. But to punish an elderly man like myself and my highly nervous and sick wife is really too much.”

The baron ended with a forlorn plea, for old time’s sake. “Could you do something to remove the net around us? This will be my last request for help and I will not annoy you any more.”

Bush sent back a sympathetic reply, assuring de Mohrenschildt that he was not the target of federal authorities and blaming his troubles on renewed media interest in the Kennedy assassination and overly inquisitive journalists.

By the following March, the sixty-five-year-old de Mohrenschildt was separated from his wife, struggling with depression, and living with family friends in a wooden bungalow tucked between the more luxurious mansions that stretched south of Palm Beach. His testimony was once again in demand—this time from the House Select Committee on Assassinations, whose investigators were showing a keener interest in the truth than the Warren panel had. On the morning of March 29, 1977, committee investigator Gaeton Fonzi rolled up outside the dark-shingled beach house, and when told that de Mohrenschildt was not at home, the congressional staffer left his card with the baron’s daughter, Alexandra. Early that evening, after returning to his Miami motel room, Fonzi got a call from Bill O’Reilly, who was working in those days as a Dallas TV reporter. O’Reilly had some stunning news. George de Mohrenschildt had been found dead at home, his head blown apart by the blast from a 20-gauge shotgun. Fonzi’s card was found in the dead man’s pocket. (In his 2012 book, Killing Kennedy, O’Reilly exaggerated his personal involvement in the drama, placing himself on de Mohrenschildt’s doorstep as the shotgun blast rang out. As subsequent news reports pointed out, O’Reilly was actually in Dallas at the time.)

The Palm Beach County coroner ruled de Mohrenschildt’s death a suicide, but his violent demise incited heated public speculation for a time. His death came amid a flurry of other sudden exits during that season of renewed congressional inquiry into the Kennedy case. Witnesses succumbed to heart attacks and suicides, or were dispatched in more dramatic ways—as in the case of Mafia-CIA go-between Johnny Rosselli, who was garroted, chopped up, stuffed into an oil drum, and dumped in Biscayne Bay. Some investigators felt the rising mortality rate of Kennedy witnesses was connected to the creeping dread in Washington that justice was finally to be done.

Was de Mohrenschildt murdered before he could begin talking to the House Assassinations Committee? Or did he take his own life, in atonement for what he had done with it? Either way, he was one more victim of the past.

If a “legend” was being woven around Lee Harvey Oswald, there was nobody who did more to move Oswald’s story along during his days in Dallas, besides George de Mohrenschildt, than a young housewife named Ruth Paine. It was Ruth Paine who took in Marina and her young children as the Oswalds’ marriage started coming apart. It was she who most closely observed the intimate details of Lee’s life. Oswald would plant clues for Ruth—like the draft of a puzzling letter to the Soviet embassy in Washington that he left on her typing desk—that made her suspect he was some sort of spy. Did he do this sort of thing on purpose? she later wondered. Was it part of the profile he was supposed to leave behind?

Ruth was the curious type—you could say even a busybody, the sort of woman who felt she could set the world straight, and it was her obligation to do so. After her husband, Michael, took an engineering job at Bell Helicopter in Fort Worth, Ruth found herself marooned in Texas—a lonely, liberal arts–educated Quaker from up north who was stuck in a cowboy culture. Her isolation only grew when she and Michael began drifting apart and he moved out of the family house into his own apartment in September 1962.

So when a friend invited her to a party at his house the following February, Ruth eagerly agreed to come. Among the other guests who would be there, she was told, was a young couple recently arrived from Russia. Ruth had taken up Russian several years before, and here was an opportunity to polish her skills with people more fluent than she.

It was the de Mohrenschildts who brought the Oswalds to the party and who introduced them to Ruth. Later, JFK conspiracy researchers made much of this, suggesting that it was not just an introduction but a “hand-off” as the de Mohrenschildts prepared to leave Dallas for Haiti. But if Ruth Paine was assuming de Mohrenschildt’s role as Oswald’s monitor, she was not doing so as a witting agent. Paine would later tell the Warren Commission that she had never met Baron de Mohrenschildt before and had not seen him since that fateful evening.

Ruth’s motives for getting tangled up in Lee and Marina’s messy lives had nothing to do with Cold War stratagems—her reasons were far more human than that. While she found Lee somewhat tedious and full of himself, she was immediately taken by Marina. “In spite of my faulty Russian, I found Marina easy to talk to and very personable,” she later recalled. Ruth got Marina’s address and wrote her soon after, asking if she could come visit her sometime. It was the beginning of a friendship that would change both women’s lives forever.

Decades later, Paine collaborated with author Thomas Mallon on a bestselling book intended to prove that there was nothing conspiratorial about the events in Dallas, only a kind of terrible serendipity. A generous young mother takes in the family of the future assassin of President Kennedy, and her life is never the same. End of story. Except that it wasn’t—Ruth’s story was far more interesting than that.

Paine is a woman of stubborn conviction, even in quiet retirement at a pleasant Quaker-run home in Northern California. She continues to dismiss all evidence of a conspiracy in Dallas as “nonsense” and—in contrast to de Mohrenschildt’s late-life conversion—she still insists on Oswald’s guilt as the sole assassin. She still wears the same sensible, bobbed haircut that she sported as a Dallas housewife, though now it’s snowy white. And, despite her advanced age, she holds herself erect, with the fierce determination of a woman who refuses to bend to time or to new information about her storied past.

During a recent visit to her home, some fifty years after the assassination, there was only a fleeting moment when Ruth acknowledged that Oswald might have been a pawn in a historical drama much larger than himself. When her visitor suggested that dreamy-eyed adventurers like Oswald can become easy prey for those with cynical intentions, she quickly nodded. “My parents had a name for that: ‘shut-eyed liberals,’” she said.

It’s a term that applies equally to Ruth Paine. In April 1963, she was thirty years old, and—like Marina—the mother of two small children and estranged from her husband, when she invited the Russian woman and her little girls to move into her modest, two-bedroom clapboard house in Irving, outside of Dallas. Paine was filled with the generosity of her faith when she took in Marina. She would grow to love Marina, she said later, “as if she were a sister.” (To some, it seemed that Ruth was also romantically infatuated with her exotic houseguest, who exuded a kind of seductive distress.) But despite Ruth’s best intentions, she helped lay waste to the Oswalds’ lives. In the end, Marina would wish she had never met her rescuer.

Ruth Paine has always scoffed at the idea that she played an intelligence role in the Oswald story. A visitor asked her point-blank if she had any contact with the CIA. “Not that I’m aware of,” she laughed. This is true, as far as it goes. Ruth and her husband, Michael, were not the cloak-and-dagger type—they were too starry-eyed and idealistic for that. But they were the sort of people who would come to the attention of security agencies. In fact, Allen Dulles himself knew all about the unusual family backgrounds of the Paines.

Ruth Paine’s parents, William and Carol Hyde—who met as Stanford University students in the 1920s—were dedicated foot soldiers in Norman Thomas’s Socialist Party crusade. Ruth remembered passing out Norman Thomas presidential campaign buttons at the Socialist Party convention in Washington, D.C., in 1940, when she was just eight years old. Her parents were also active members of the cooperative movement, and William went to work as an executive for Nationwide Insurance, a company that originated as a co-op. The Hydes’ involvement in the Socialist Party and co-op movement brought them into bare-knuckled conflicts with the Communist Party, which was in the habit of trying to muscle in on left-wing enterprises that had energy and promise.

The CIA, which took a strong interest in the anti-Communist left, eventually took an interest in Ruth’s father. According to a CIA document, Hyde was considered “for a covert use” in Vietnam in 1957, but for unexplained reasons the agency decided not to utilize him. Hyde did work for a year in Peru, setting up co-op credit unions for the U.S. Agency for International Development (AID), an organization whose work was often entwined with that of the CIA. Government documents suggest that Ruth’s sister, Sylvia, later went to work for the CIA, and Sylvia’s husband, John Hoke, was employed by AID.

In short, the young Dallas housewife who took the Oswald family into her care was not simply a Quaker do-gooder but a woman with a politically complex family history. She grew up in that strongly anti-Communist wing of the American left that overlapped with the espionage world. Ruth Paine was not an operative herself, but there was a constellation of dark stars hovering all around her, even if she chose not to pay attention.

But it was the family background of Ruth’s husband, Michael, that most directly overlapped with Allen Dulles’s world. Mary Bancroft, Dulles’s mistress, was one of the oldest friends of Michael Paine’s mother—also named Ruth. Michael’s parents, George Lyman Paine Jr. and Ruth Forbes Paine, were the kind of odd ducks that Mary liked collecting—quirky offspring of prominent New England heritage with minds as restless as hers. Lyman was an architect and a gentleman Trotskyite whose political activities earned him a place on the FBI’s watch list. Ruth Forbes Paine hailed from a Boston blue-blood family that had made its fortune from the China tea and opium trade, and counted Ralph Waldo Emerson among its progenitors. She would give herself over to the pursuit of world peace and the exploration of human consciousness. In the 1920s, Mary was a regular at the salons presided over by Lyman and Ruth in their spacious studio apartment on the Upper East Side—gatherings that drew a colorful menagerie, including artists, trust-fund revolutionaries, truth seekers, and other devotees of the esoteric.

Ruth Forbes Paine came from such established Yankee wealth that her family owned its own island, Naushon Island, off Cape Cod. After she and Lyman divorced, Ruth would take her sons, Michael and Cameron, to summer on the island. The Forbes family often extended invitations to their circle of friends to join them in the cottages on their private paradise. Among those invited to Naushon Island by Ruth Forbes Paine were Mary Bancroft and Allen Dulles.

As the Warren Commission went about its business, Mary wrote Dulles chatty letters about the Forbes and Paine families, and their horrified reaction to the events in Dallas, as if she were back in wartime Switzerland and still filing espionage reports. Bancroft reminded Dulles that she had known Michael Paine’s mother “extremely well” for over forty years and had spent summers with her on Naushon Island. She enumerated the families’ many lovable oddities and their sense of grand entitlement. “I was always fascinated by those proper Boston homes—and by the Forbes family at Naushon where I spent a lot of time,” wrote Mary in a March 1964 letter to Dulles. “In those homes, anyone could say absolutely anything—everything was accepted and examined. One met labor leaders, pacifists, Negroes—everything but Catholics! Lyman Paine, Ruth’s first husband and Michael Paine’s father, came from a similar background—authentic, proper Bostonians, the kind of people who still believe today that the U.S. is their invention on lease to all the rest of us.”

In another letter to Dulles, Mary summed up the privileged and politically eccentric world of the Paines by making a devastating comparison—one that had certainly already occurred to Dulles. “I would only like to point out that this is the same kind of ‘background’ that one runs into with both Noel Field and Alger Hiss—this Quaker–early American family thing.” Dulles knew this type well—he had a history of putting such people to good use. They were the blissful do-gooders who later wondered how they had stumbled into history’s grinder.

It was another striking “coincidence” in the endlessly enigmatic Oswald story. The housewife who took the Oswalds under her wing had married into a family whose foibles and weaknesses were well known to Dulles and his mistress. Ruth Paine was aware of her mother-in-law’s connection to Bancroft and Dulles. Her mother-in-law, in fact, had told her that she invited the couple to enjoy a get-away on the family island. But with typical obstinacy, Ruth refused to see any particular significance in this Dulles link to her family.

Dulles himself acknowledged the flat-out weirdness of these curious facts and, in his own characteristic fashion, simply laughed it off. The conspiracy-minded would have a field day, he chuckled, if they knew that he had visited Dallas three weeks before the assassination and that he had a personal connection to the woman whom he identified as Marina Oswald’s “landlady.”

But Ruth Paine was more than that. She was also the woman who—the month before JFK’s arrival in Dallas—informed Lee about the job opening in the Texas School Book Depository, the warehouse building that loomed over the final stretch of President Kennedy’s motorcade route. Ruth had been told about the warehouse job by a neighbor. The building was owned by yet another intriguing character in the Oswald drama, right-wing Texas millionaire, David Harold Byrd.

D. H. Byrd received scant attention after the Kennedy assassination, despite his building’s role in the crime. The Warren Commission never questioned him, and reporters did not profile him—even after the millionaire took the odd step of removing the eight-pane window from which Oswald allegedly fired his shots at Kennedy’s limousine and hanging it in his Dallas mansion. Byrd said he feared that souvenir hunters might steal Oswald’s so-called sniper’s perch from the book warehouse, but he displayed the infamous window in his own home like a trophy.

Byrd’s name was woven through the turbulent politics of the Kennedy era. He was a crony of Lyndon Johnson and a cousin of Senator Harry Byrd of Virginia, a white supremacist and a leader of the rising conservative movement. He also belonged to the Suite 8F Group, an association of right-wing Texas tycoons that took its name from the Lamar Hotel room in Houston where they held their meetings. The group included George Brown and Herman Brown of Brown & Root—a construction giant built on government contracts—and other military industrialists and oil moguls who had financed the rise of LBJ.

The owner of the Texas Book Depository was closely associated with a number of passionate Kennedy adversaries, including Curtis LeMay, the Air Force chief whose relentless quest for a nuclear showdown with the Soviet Union caused the president to question the general’s sanity. LeMay bestowed a glowing Air Force commendation on Byrd in May 1963 for his role in founding the Civil Air Patrol, the military auxiliary group that counted a teenaged Oswald among its cadets.

Did Byrd and his associates in the national security field use Ruth Paine to maneuver Oswald into the Texas Book Depository by passing word of the job opening to her through her neighbor? Always looking for ways to help the distressed couple in her care, Ruth quickly tipped off Lee about the job. The earnest Quaker might have played a pivotal role in unknowingly sealing his fate. But one way or the other, Oswald seemed doomed to end up in the building and to meet his date with infamy. By October 1963, when he went to work in the building, there were too many unseen forces at work on the young man—who turned twenty-four that month—for him to call his life his own.

In the months leading up to the Kennedy assassination, Oswald was moved here and there with the calculation of a master chess player. In April, he returned to his hometown, New Orleans, with Marina and the girls, where he called attention to himself by jumping into the combustible world of Cuban politics. He reached out to the Fair Play for Cuba Committee, the leading pro-Castro group in the United States, which was the target of such heavy FBI and CIA pressure that its two founders later succumbed and offered their services as government informers. At the same time he was dallying with the Fair Play for Cuba Committee, Oswald also made contact with the Directorio Revolucionario Estudiantil (DRE)—a group of young, militant, anti-Castro Cuban exilesoverseen by the CIA’s point man on Cuba, David Phillips. Playing both sides of the Cuba fence, Oswald began passing out Fair Play leaflets in the streets while working out of the same building where Guy Banister, a former FBI agent who was involved in anti-Communist operations, maintained his office.

Oswald’s double-dealing was bound to lead to a blowup, and in August it did, when he was angrily confronted by DRE activists while passing out his pro-Castro flyers. A New Orleans police lieutenant who later investigated the tussle reported that Oswald seemed to have staged the whole thing “to create an incident—but when the incident occurred, he remained absolutely peaceful and gentle.” The New Orleans fracas recalled Oswald’s theatrics in the U.S. embassy in Moscow, where he had announced his defection.

In early September, Oswald popped up again in Dallas, where he and his family would move back later that month. This Oswald sighting is an extremely suggestive one, since he was spotted in the company of none other than David Atlee Phillips—one of the more glaring indications that the ex-marine was the focus of an intelligence operation. Oswald and Phillips were observed talking together in the lobby of a downtown Dallas office building by Antonio Veciana, a prominent Cuban exile leader whose violent group, Alpha 66, had come close to killing Castro with a bazooka attack. Veciana—who arrived at the Dallas building for his own meeting with Phillips, his CIA supervisor—would later recognize the slight, pale man he had seen with Phillips that afternoon, when Oswald’s face was splashed across front pages and TV screens. Phillips had trained him well, Veciana later said. “He taught me how to remember faces, how to remember characteristics. I am sure it was Oswald.”

Veciana told his story to House Assassinations Committee investigator Gaeton Fonzi in the late 1970s and later repeated it to journalists. But even when the aging exile leader climbed onstage at a Washington conference of JFK assassination researchers in September 2014 to retell his remarkable story, the mainstream press still did nothing to spotlight it. “I was trained by the CIA, as was Oswald,” said Veciana, who was the accounting manager for a Havana bank before he joined the anti-Castro movement. “Oswald and Fidel Castro were ideal scapegoats for the murder of the president. . . . It really was a coup d’etat.”

In late September, Oswald took a bus trip to Mexico City and again made a spectacle of himself while trying in vain to obtain travel visas for Cuba at the Cuban and Soviet embassies. While Oswald visited Mexico City, someone impersonating him made phone calls to the Cuban and Soviet embassies—calls that were intercepted on CIA surveillance tapes. The agency later claimed that these tapes were routinely destroyed. But J. Edgar Hoover himself listened to them immediately after the assassination and the FBI chief informed Lyndon Johnson, the new president, that the voice on the tapes was not Oswald’s. Both men knew the stunning significance of this audio fakery by the CIA—it showed that Kennedy’s alleged killer was somehow entangled in espionage business. He was not simply a deranged loner.

In the final weeks of his life, Oswald was the subject of particularly intense CIA coverage. Much of this scrutiny emanated from the offices of Jim Angleton and David Phillips. After sifting through declassified government documents from this period, John Newman—a University of Maryland history professor and former U.S. military intelligence officer—concluded that the agency had demonstrated “a keen operational interest in Oswald.” Newman’s skilled decryption of the intelligent design behind Oswald’s activities—which he first outlined in his 1995 book, Oswald and the CIA—was a historical breakthrough in understanding the alleged assassin’s mysterious life.

Oswald was ostensibly being closely tracked by the CIA as well as by the FBI because he was a recent defector and a self-proclaimed revolutionary. But, as President Kennedy prepared to visit Dallas, something curious occurred within this surveillance labyrinth. On October 9, Oswald was suddenly removed from the FBI “FLASHLIST”—the bureau’s index of suspicious individuals to be kept under close watch. FBI officials took this surprising step despite Oswald’s suspicious behavior in Mexico City. The day after the FBI took Oswald off its watch list, the CIA also downgraded him as a security risk. On October 10, four senior counterintelligence officials who reported to Angleton and Helms signed off on a curious cable to the CIA station chief in Mexico City, assuring him there was no reason to be concerned about Oswald because his stay in the Soviet Union had a “maturing effect” on him.

These signals about Oswald circulating in the intelligence community had a fateful effect. By being downplayed as a security risk, Oswald became an unchecked pawn, free to be moved wherever he was useful.

Appearing before the Warren Commission, Ruth and Michael Paine seemed confused and tentative when it came to assigning guilt to Oswald. They both agreed that while he was a man of headstrong convictions, he did not impress them as a dangerous sort, and, like George de Mohrenschildt, they said Oswald rather liked Kennedy. “I had never thought of him as a violent man,” Ruth testified. “He had never said anything against President Kennedy. . . . There was nothing that I had seen about him that indicated a man with that kind of grudge or hostility.”

Michael—a lean man with sensitive eyes and a soft, watery demeanor—seemed particularly at sea when he tried to make sense of Oswald. When Dulles asked him if he was convinced that Oswald was the assassin, Michael launched upon a rambling, only somewhat coherent reply, winding up with this less-than-decisive conclusion: “I never did discover—and it didn’t quite make sense, but for the most part, I accept it, the common view that he did it.”

In truth, Michael never knew Oswald very well. They only talked at length on about four occasions, he told the Warren Commission. They would run into each other some weekends when they visited their wives and kids at the Paine family house in Irving. One evening, Michael took Oswald to a meeting of the local chapter of the ACLU, which the Paines belonged to. Afterward, Lee told Michael that he could never join a civil libertarian group like that because it wasn’t sufficiently militant.

Neither of the Paines was fond of Oswald. To Ruth, he was an opaque, self-involved, and ill-tempered man who could be cruel to Marina. He was just part of the equation that she had to put up with in order to have Marina in her life. “I would have been happy had he never come out, indeed happier had he not come out on the weekends,” she would testify.

Michael and Lee seemed to have more in common—two men who had grown up, for the most part, without fathers, and were now struggling to hold on to their own families. There was something lost about both young men, a searching quality that left them too open to new experience. But they never really hit it off with each other. Lee was too “dogmatic” for Michael, too set in his Marxist ways. He reminded him of his distant Trotskyite father, too wrapped up in his adamant political theories to connect with other people.

Apart from providing a few suspicious, circumstantial details, this was the Paines’ main contribution to establishing Oswald’s guilt. Guided primarily by Warren Commission lawyers Albert Jenner and Wesley Liebeler—as well as by Dulles—the couple painted a portrait of Oswald as a grim subversive.

But the Paines also confirmed Oswald’s guilt by just being themselves. Here were two left-wing oddballs—their appearance before the panel seemed to signify—a man and woman with peculiar and vaguely seditious family pedigrees. They were just the type whom you would expect to unwittingly harbor a dangerous man like Oswald. In their immaculate innocence, the Paines played right into the hands of those who were manipulating Oswald.

The Paines reunited for a time after the assassination but later divorced. In old age, they now live in the same Quaker retirement compound north of San Francisco, connected by the bonds of time. Not long ago, Michael sat down for an interview at the nearby commune where their middle-aged son, Christopher, and two dozen or so others live—a ramshackle collection of cottages in a green gulch near the Russian River that Ruth calls “a latter-day hippie ranch.” Sitting on a lumpy couch in one of the cottages, the retired engineer came across as boyishly charming and given to whimsical ideas—an “innocent,” as Ruth described him.

While serving with the Army in the Korean War, Michael mentioned at one point during the afternoon, “I thought of going over to the other side and saying to the Chinese, ‘We don’t have to fight like this.’ But I thought I’d be blown up if I did. I also thought it would be unlikely I could find someone I could talk to, and they’d put me in a concentration camp. I prefer democracy, but I thought communism for China was an appropriate thing—they needed to all go in the same direction.” This is the sort of idiosyncratic thinking that might well have made Michael Paine stand out to someone like Dulles.

The Paines seemed to grow more convinced of Oswald’s guilt over time. But nowadays Michael is not as cocksure as Ruth. As he talked about those ancient, catastrophic days, he seemed bewildered, like someone trying to explain a collision he had survived long ago. He still wavered back and forth, just as he did with the Warren Commission. “Oswald wanted to overthrow something, the enemies, capitalists, the oppressors . . . he wanted action, and you had to be tough, brutal.” But then again . . . he liked Kennedy. “Oh, he did! He said, ‘JFK is my favorite president.’”

Michael Paine still does not know what to think. But perhaps, like the rest of the country, he has found a kind of comfort in his confusion.

As November 22, 1963, dawned—the day John F. Kennedy would die—Allen Dulles was away from Washington, as he typically was at the outset of major operations. In September and October, Dulles had maintained the busy schedule of a man still in the thick of clandestine affairs, meeting with key officials from the CIA’s covert action side such as Desmond Fitzgerald, who—along with David Phillips—oversaw the violent intrigue swirling around Cuba; Angleton and his deputy, Cord Meyer; and a top Helms aide, Thomas Karamessines. All of these men would later be connected by investigators, in one way or another, to the Kennedy assassination.

But as Friday, November 22, drew near, Dulles spent much of his time away from his Georgetown home base. His book tour for The Craft of Intelligence provided the spymaster with a good excuse to get away from home. In the days leading up to the assassination, he made bookstore and media appearances in Boston and New York. Early on the morning of November 22, Dulles caught a Piedmont Airlines flight back to Washington, landing at National Airport around 8:30 a.m. He was then driven to a hotel in Williamsburg, Virginia, where he addressed a Brookings Institution breakfast meeting. After receiving the news from Dallas, around 1:30 that afternoon, Dulles took a car back to Washington with John Warner, a CIA attorney.

But, according to Dulles’s date book, he did not spend the evening at home in Washington. He headed back to the northern Virginia countryside, where he would spend the entire weekend at a top secret CIA facility known officially as Camp Peary, but within the agency as “the Farm.”

At the time of the Kennedy assassination, Dulles had no formal role in government. As far as the public knew, he was a figure of the legendary past, a graying gentleman who supplemented his civil service pension by recycling colorful espionage tales of yesteryear and by delivering sobering Cold War speeches. But the Farm was not a club for CIA retirees. It was a bustling clandestine center that Dulles himself had inaugurated soon after taking over as CIA chief, and it served a variety of tightly guarded functions.

Before the CIA took over Camp Peary—a sprawling compound in the densely wooded tidelands near Williamsburg—it was used as a Navy Seabees base and then as a stockade for captured German sailors. Dulles turned it into a spy training base for recruits who were headed overseas. According to former CIA agents Philip Agee and Victor Marchetti, among the well-trained professionals turned out by the Farm were skilled assassins. The facility was also what would later be termed a “black site”—a secure location where enemy captives and suspicious defectors were subjected to extreme interrogation methods.

As CIA director, Dulles had built himself a comfortable home at the Farm. Years later, consultants like Chalmers Johnson—an Asian affairs expert who became a scorching critic of U.S. empire—would be housed there during agency conferences. Johnson recalled the retired spymaster’s well-stocked library, which—as late as 1967—still contained the latest CIA reports, intelligence estimates, and classified journals.

“The Farm was basically an alternative CIA headquarters, from where Dulles could direct ops,” said former congressional investigator Dan Hardway.

This is the CIA command post where the “retired” Dulles situated himself from Friday, November 22, through Sunday, November 24—a highly eventful weekend during which Oswald was arrested and questioned by Dallas police, Kennedy’s body was flown back to Washington and subjected to an autopsy riddled with irregularities, and Oswald was gunned down in the basement of the Dallas police station by a shady nightclub owner.

A year after the assassination, Dulles was interviewed by an old CIA colleague, Tom Braden, for the oral history project at the JFK Library in Boston. Braden asked Dulles what he had thought of Kennedy “as a man.” Dulles put on his mask of mourning and sympathy, as he could do in an instant. “Oh, I rated him high. . . . I shall never forget when I first heard the news of the Dallas tragedy. I felt that here is a man who hadn’t had the chance really to show his full capabilities, that he was just reaching a point where his grasp of all the intricacies of the presidency were such that now he could move forward.”

While serving on the Warren Commission, Dulles told Braden, he had the opportunity to examine the assassination in exquisite detail. He talked about the events of that day as if he were inspecting the inner mechanism of a fine watch. He seemed in awe of the intricate meshing of synchronicities that had to occur in order for Kennedy to die that day. His description made it sound like the operation of a lifetime.

“If the employees of the Book Depository had eaten their lunch in a little different place,” said Dulles, “if somebody had been at one place where he might easily have been instead of another at one particular time—the ‘ifs’ just stand out all over it. And if any one of these ‘ifs’ had been changed, it might have been prevented. . . . It was so tantalizing to go over that record [of events], as we did, trying to find out every fact connected with the assassination, and then to say if any one of the chess pieces that were entered into the game had been moved differently, at any one time, the whole thing might have been different.”

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