Rome on the Potomac

By the evening of June 16, 1962, when bow-tied Arthur Schlesinger Jr. went tumbling fully clothed into the swimming pool at Hickory Hill, Robert and Ethel Kennedy’s estate in suburban Virginia, the dunking of party guests had become a New Frontier ritual. Dinner parties at Hickory Hill, where dogs and children ran wild through the house and across the rolling lawns, were already a colorful part of Washington society lore. Invitations to Bobby and Ethel’s backyard fests signaled insider status in the youthful Kennedy court. Judy Garland sang; Harry Belafonte did the twist; national heroes like astronaut John Glenn faced bold, new challenges. On this particular evening, Glenn, who had recently become the first American to orbit the earth, was dared by the rambunctious Ethel to sit with her at dinner—on a plank that had been laid precariously across the pool. The astronaut succeeded in staying dry, but Ethel ended up in the pool when Schlesinger and another guest began mischievously bouncing up and down on the wobbly board. Later, as Schlesinger chivalrously leaned down to help Ethel out of the water, a prankster bumped him and the respected Harvard historian went headlong into the pool, taking the attorney general’s wife down with him.

The raucous antics of the Kennedy crowd were greeted by much of the Washington establishment as a welcome relief from the fusty Eisenhower regime. The Kennedy brothers and their team brought such relentless vigor to their jobs, they were allowed to blow off steam in their off-hours. There had been no scolding in the press, for instance, the year before when Senator Edward M. Kennedy, the president’s fun-loving baby brother, had emerged from his own swimming pool baptism at Hickory Hill, “a huge, dripping mass in a now hopelessly rumpled dinner jacket,” as Schlesinger recalled.

But by June 1962, the Kennedy administration was deeply embattled, from within and without. And the Kennedy circle’s unrestrained merrymaking now was regarded as unseemly in some quarters. Drew Pearson noted in his column that “Southern congressmen were especially interested in the fact that Ethel Kennedy, sister-in-law of the president, twisted with Harry Belafonte, well-known Negro singer.” Meanwhile, Schlesinger’s swimming pool high jinks were splashed across the front page of the anti-Kennedy New York Herald Tribune. As JFK’s main link to the liberal intelligentsia and left wing of the Democratic Party, the White House adviser had become an especially tempting political target.

Henry J. Taylor, a syndicated newspaper columnist, led the press campaign against Schlesinger, taking advantage of the embarrassing publicity over his Hickory Hill water sports to level other charges against Kennedy’s court philosopher. Taylor accused Schlesinger of violating the White House code of ethics by moonlighting as a freelance writer, churning out political essays for publications like The New York Times and The Saturday Evening Post, and doing movie reviews for a chic new glossy magazine calledShow.

It turned out that the White House had no such ban against outside freelancing and that Kennedy, an ardent movie lover, thoroughly enjoyed Schlesinger’s reviews. One night, when Roger Vadim’s arty vampire movie Blood and Roses was being screened in the White House projection room, a bored Kennedy got up halfway through the feature and told Schlesinger he would be content to read his review. Before he left, the president shared some of his own rather sophisticated movie opinions with Schlesinger, urging him to do a comparative review of the Italian film Girl with a Suitcase and A Cold Wind in August, an obscure independent feature. He then declared his disappointment with Breakfast at Tiffany’s and expressed his regret “that Hollywood had no guts any longer and could not do a sharp or interesting film.”

Taylor’s attack on Schlesinger—in which he warned of the liberal historian’s pernicious influence on Kennedy policy—spread to other media outlets, including Time magazine, which poked fun at Schlesinger’s Hickory Hill frivolity and, taking the opposite tack from Taylor, questioned whether he really did much of anything as “special assistant” to President Kennedy. Thomas “Tommy the Cork” Corcoran, FDR’s legendary adviser and a longtime Washington power broker, didn’t like the beating that Schlesinger was getting in the press and he phoned his young friend at the White House. “I scent a manhunt,” Corcoran told Schlesinger. “The play they gave to the swimming pool story was the tip-off. They are out to get you.” The Cork warned Schlesinger that he had heard Republicans were spreading a vicious story that they had found someone claiming to be an old Harvard classmate of Schlesinger, and “he will swear that he knew you then as a member of the Communist Party.”

In the midst of the media furor, Schlesinger felt tempted to offer Kennedy his resignation. Late one afternoon, when Schlesinger went to see the president in the Oval Office on another matter, JFK asked him how he was holding up. “It’s been a bad couple of days,” he told Kennedy. The president responded in a “kindly way,” Schlesinger noted in his journal. “Don’t worry about it,” JFK told his downcast adviser. “Everyone knows that Henry Taylor is a jerk. All they are doing is shooting at me through you.”

The media attack on Schlesinger bore the fingerprints of the Dulles group. Though he’d been out of office for half a year, Dulles’s influence remained strong in the press—particularly with Luce publications like Time. Henry Taylor, too, had ties to the Dulles brothers, having served in Foster’s diplomatic corps as ambassador to Switzerland before becoming a syndicated columnist for United Features.

On first glance, Schlesinger seemed like an unlikely target for the Dulles network, since he, too, had enjoyed a friendly relationship with the intelligence chief, dating back to World War II, when the young historian was one of many intellectuals recruited by the OSS. As an OSS analyst stationed in London and Paris during the war, Schlesinger held strongly anti-Communist views; after the war, Schlesinger became a leading architect of Cold War liberalism, joining the anti-Soviet propaganda campaign that was secretly funded by the CIA and endorsing efforts to root out Communist Party influence in the labor movement, cultural arena, and academic circles.

Schlesinger was a passionate believer in New Deal liberalism, which he saw as the only way to civilize capitalism. And he was an equally ardent anti-Communist, viewing the anti-Red crusade as a way to protect the American left, by ridding it of the Stalinist contamination that had seeped into Democratic Party circles during FDR’s necessary wartime alliance with Moscow. Schlesinger believed that it was vital to purge these Communist Party influences, even though the CP’s well-organized shock troops were behind many of the political and labor victories of the New Deal period, in order to fend off attacks from the right that sought to label liberalism as a paler version of Marxist-Leninism.

In 1949, Schlesinger endorsed a crude effort by Luce’s Life magazine—which the young, Pulitzer Prize–winning historian sometimes wrote for—to develop a blacklist of celebrities that the magazine described as “Dupes and Fellow Travelers” of the Communist Party. Along with the predictable stalwarts of the Far Left, Life listed such liberal luminaries as Albert Einstein, Arthur Miller, Norman Mailer, Aaron Copeland, and Leonard Bernstein. Schlesinger gave the Life magazine blacklist his stamp of approval, calling it “a convenient way of checking the more obvious Communist-controlled groups.”

Though Schlesinger was an avid New Dealer, he was also a pampered product of the American elite—the son of esteemed Harvard historian Arthur M. Schlesinger Sr., a graduate of exclusive Phillips Exeter Academy at fifteen, a summa cum laude graduate of Harvard at twenty, and, at twenty-seven, winner of the Pulitzer Prize for his masterful work The Age of Jackson. Raised in the rarefied intellectual atmosphere of Cambridge, where the likes of James Thurber, John Dos Passos, H. L. Mencken, and Samuel Eliot Morison circulated through his family home, young Schlesinger “never stopped seeming like the brightest student in the class,” as The New York Times observed.

Critics like C. Wright Mills and revisionist historian William Appleman Williams charged that Schlesinger—coddled by the East Coast establishment and subsidized by CIA front groups—clung to a one-sided view of the Cold War, placing sole responsibility for the tense, global standoff on Moscow. Russia was not merely seeking a protective buffer when it took control of Eastern Europe following the epic destruction of World War II, Schlesinger insisted; in his view, the Soviet Union was a “messianic state” whose “ideology compelled a steady expansion of Communist power.” Even after the collapse of Stalin’s regime, Schlesinger saw no significant modification in this implacable Soviet expansionism.

Not surprisingly, Schlesinger maintained friendly, if somewhat remote, relations with Allen Dulles throughout the 1950s. The Cold War consensus that dominated Democratic as well as Republican circles made for unlikely alliances; Schlesinger counted a number of top CIA officials among his friends, including Helms, Wisner, and Bissell, and he often joined them on the Georgetown cocktail circuit. Washington Post publisher Philip Graham and columnist Joe Alsop hosted the parties where the disparate Dulles and Kennedy entourages all intermingled.

Schlesinger had his differences with the CIA crowd, going back to his OSS days. He had been offended by “the notion of American spooks” like Dulles and Wisner “cheerfully consorting with people like General Reinhard Gehlen. . . . There was something aesthetically displeasing about Americans plotting with Nazis, who had recently been killing us, against Russians, whose sacrifices had made the allied victory possible.” During the Eisenhower-Dulles years, Schlesinger found much more that was “aesthetically displeasing” about the Republican reign. “The Dulles brothers,” sniffed Schlesinger’s first wife, Marian, years later, “were self-righteous and egomaniacal.” By the time Kennedy took office, Marian Schlesinger, a product of the same Cambridge background as her husband, regarded Allen Dulles as “passé.”

But in the name of Cold War fraternity, Schlesinger was willing to make his own political compromises—even with men like Allen Dulles, whose Wall Street Republicanism and bullying foreign interventionism represented everything the historian opposed. Schlesinger made an effort to maintain cordial relations with the CIA chief, keeping up a friendly correspondence with Dulles that lasted late into the Old Man’s life. Schlesinger wrote a favorable review of Germany’s Underground, Dulles’s 1947 book on anti-Hitler wartime intrigues, which elicited a warm thank-you note from the spook. Over dinner at Phil Graham’s house in March 1958, they discussed Doctor Zhivago, Boris Pasternak’s epic lament about the fragility of love and the human spirit in the grinding machinery of twentieth-century Russian history. CIA officials believed that the novel, which had been banned in the USSR, had “great propaganda value,” and they were planning to sneak copies into Pasternak’s homeland, though the author himself came to regret the political exploitation of his book.

On November 29, 1961, as Dulles was ushered out the door at the CIA, Schlesinger wrote to him again, telling the spy chief that it had been a “privilege” to work with him and urging him to write his memoirs: “You have had a fascinating life, and you owe it to your fellow countrymen to put it down on paper.” Dulles responded warmly two weeks later, telling the historian that he was mulling over a couple of book ideas “and may seek your wise counsel.”

Nobody in Washington was better positioned than Arthur Schlesinger Jr. to observe the growing split in Kennedy’s government. He had played a leading role in the formation of the Cold War consensus that had held together Washington’s opposing political camps. But that consensus began to shatter early in the Kennedy presidency, and Schlesinger found himself maintaining a delicate balancing act, with one foot on each side of the divide. In the months following the Bay of Pigs crisis, the cracks continued to lace their way through the administration, as JFK resisted the belligerent advice from his national security advisers and tried to maneuver his way around the minefields of Cuba, Laos, Berlin, and Vietnam. Kennedy drew more ire from his warlords—including men like Lemnitzer and Air Force chief Curtis LeMay, whom JFK considered mentally unbalanced—when he brusquely dismissed their persistent pleading for a nuclear confrontation with the Soviet Union and instead pursued a test ban treaty aimed at slowing down the race toward doomsday.

Following the Bay of Pigs, Schlesinger found his relations with the CIA crowd strained, but he still was invited to their dinner parties, and his Langley friends—like Helms, Ray Cline, and Cord Meyer—continued to keep him apprised of the agency’s mood. Meanwhile, Kennedy, despite his occasional bemusement at Schlesinger’s ivory-tower liberalism, increasingly drew the historian into his inner sanctum. Schlesinger earned points with JFK, not only by giving him the correct advice on the Bay of Pigs—“a great mistake’’—but by resisting the temptation to crow about his wisdom to the press following the disaster, as some administration officials had done.

Kennedy soon began seeking the historian’s advice on everything from nuclear policy to the handling of prickly liberal critics like Alfred Kazin, whom Kennedy sought to charm, on Schlesinger’s advice, by inviting him for lunch at the White House in August 1961. Kennedy was nervous about meeting the formidable New York intellectual, suggesting that Jackie be invited too—“she knows all those obscure French writers.” When Kazin arrived at the White House, JFK was at his dazzling best, offering fascinating insights into everyone from Malraux to Khrushchev, but he still fell short with the scholar, who later described the president as “slick, cool and devoid of vision.” When Schlesinger reminded him that left-wing intellectuals said the same thing about FDR, Kazin replied that he was one of those who did. “And I still believe today that I was absolutely right!” Kazin declared.

Schlesinger, however, was the type of intellectual who saw nothing wrong about entering the inner circle of power to serve a Roosevelt or a Kennedy. He derided those cloistered academics who remained on the sidelines, speculating about the twists and turns of history but never actually participating in their times. In the beginning of his presidency, Kennedy was a bit nervous about having a bestselling historian on his White House staff. Coming across Schlesinger pounding away at his typewriter one day in his remote East Wing office, JFK smiled, “Now Arthur, cut it out. When the time comes, I’ll write The Age of Kennedy.” But after the Bay of Pigs, feeling increasingly besieged within his own administration, Kennedy embraced Schlesinger’s role as court chronicler. The president encouraged Schlesinger to begin taking notes at White House meetings. “You can be damn sure that the CIA has its records and the Joint Chiefs theirs,” JFK told him. “We’d better make sure we have a record over here.”

Schlesinger’s journal entries, letters, and memos provide a fascinating and invaluable inside look at the increasingly acrimonious civil war that would tear apart Kennedy’s government. Critics often denounced Schlesinger as a toady to power, and there is no doubt that he fell under the spell of Camelot, sharing intimate weekends with the first couple at Hyannis Port and drinking champagne with the Kennedys on board their sailboats off Cape Cod and on the Potomac. During the Bay of Pigs debacle, Schlesinger took a particularly strong blast from the left, with C. Wright Mills denouncing “Kennedy and company” for “return[ing] us to barbarism,” and singling out JFK’s in-house historian, whom Mills charged had “disgraced us intellectually and morally.”

But critics like Mills were not privy to the internal battles that raged within the Kennedy administration. In reality, Kennedy and trusted advisers like Schlesinger were determined to check the forces of “barbarism,” not to succumb to them—and their efforts set off a powerful backlash within the president’s own bureaucracy. The struggle fought between JFK and the national security elite, as Kennedy attempted to lead the country out of the Cold War, was largely invisible to the American people. Nor was it fully understood by observers like Mills, who died of a heart attack at forty-five in March 1962, before the Kennedy court drama reached its violent climax. Schlesinger himself did not entirely grasp the forces at play as he recorded the daily turmoil of the Kennedy presidency. But the picture that clearly emerges from reading his insightful journals and memos decades later is one of a government at war with itself.

The relationship between Kennedy and Schlesinger took a back-and-forth course, as the two men began to reevaluate America’s Cold War policies. Sometimes it was the president whose thinking was boldest, other times it was his adviser who pushed Kennedy to be more courageous. The president’s subtle grasp of U.S.-Soviet dynamics had the effect of making Schlesinger’s own Cold War philosophy less rigid and more sophisticated. By 1963, Kennedy would come to the conclusion that “the hardliners in the Soviet Union and the United States feed on one another”—an observation that struck Schlesinger as wise. Kennedy liked to surround himself with intelligent men, but he was usually the most perceptive man in the room. He had a way of raising the thinking of his “best and brightest” to a higher level.

When it came to domestic politics, JFK was a shrewd strategist, and he thrashed out decisions by reviewing them with longtime political confidants and war horses, like his brother Bobby and special assistant Kenny O’Donnell. But Kennedy also realized that his political pragmatism could sometimes compromise his vision. So he often relied on New Frontier true believers like Schlesinger to be his voices of conscience and liberal touchstones. At other times, JFK used Schlesinger almost as a comic foil.

One day, Schlesinger urged Kennedy to replace Dean Rusk, a bland mouthpiece of Council on Foreign Relations conventional wisdom, with a more stimulating secretary of state. Kennedy glanced up at his adviser from a paper on his desk that he was perusing. “That’s a great idea, Arthur,” he said. After Schlesinger left his office, JFK turned to O’Donnell, who had been quietly taking in the bold pitch for revitalizing the State Department, and laughed. “Arthur has a lot of good ideas,” the president told O’Donnell.

Schlesinger himself sometimes questioned his relevance within the Kennedy administration. “I have the feeling that the president somewhat discounts my views,” the White House aide wrote in his journal in September 1962, “primarily because he regards me as a claimant agency for standardized liberalism, partly also because he considers me to be, after all, an intellectual and insufficiently practical and realistic.”

But by 1963, the president himself was telling his brother and Phil Graham that he was seriously considering replacing Rusk with Robert McNamara, who had proven a smart and reliable ally in Kennedy’s battles with the Pentagon’s warlords.

Arthur had a lot of good ideas, and though he was careful not to overstep his bounds, he was unfailingly articulate and often persistent in the way he espoused them. His insights and suggestions had a way of working themselves into the recesses of Kennedy’s mind. The president had been an avid reader of history since he was a boy, and here on his staff was someone who could raise the big historical questions at the very moment that the administration was making history. No wonder academic colleagues like Richard Rovere got somewhat carried away and compared Schlesinger’s role in the Kennedy White House to that of Voltaire and Aristotle in the courts of Frederick and Alexander the Great. No prominent intellectual had held such a post of freewheeling influence in U.S. presidential history.

Schlesinger’s most intrepid moment in the Kennedy presidency would come after the Bay of Pigs, when he boldly schemed to bring the CIA under presidential control, which neither Truman nor Eisenhower had been able to do. It took courage for Schlesinger to confront his old friends at the spy agency, some of whom denounced him as a traitor. The battle to take charge of the CIA would become the most fateful drama of the Kennedy presidency.

Schlesinger began lobbying Kennedy to play a big role in reorganizing the CIA even before the smoke had cleared from the Cuba debacle. He wanted to make sure that the current tempest over the agency did not simply fade away, resulting once again in a blue-ribbon oversight committee controlled by “Dulles stooges,” as he put it. In an April 21, 1961, memo to the president Schlesinger wrote, “It is important, in my judgment, to take CIA away from the Club.” Schlesinger was not enthusiastic about Kennedy’s choice of General Taylor to oversee the White House’s Bay of Pigs postmortem, regarding the general as “very pleasant [but] a man of limited interests and imagination.” Nor was Taylor the sort of crusading official who would follow through on Kennedy’s angry impulse to “splinter the CIA into a thousand pieces.” The general, Schlesinger noted, “is quite cautious and does not seem disposed toward drastic reorganization of the intelligence services.”

But it was Schlesinger whom Kennedy tapped to develop an ambitious CIA reorganization plan, while Taylor was limited to the Bay of Pigs inquest. The historian was able to convince JFK of his qualifications for the job, reminding him, “I served in the OSS during the war, and I have been a CIA consultant for a good deal of the period since; so that, while I am far from a professional in this field, I am a relatively experienced amateur.”

Schlesinger threw himself into the CIA study with scholarly dedication, amassing a thick file that contained detailed critiques of the organization by Washington liberals like George McGovern and agency whistle-blowers, one of whom wrote, “The Central Intelligence Agency is sick.” Schlesinger also compiled disparaging essays and investigative features about the Dulles reign from the liberal press, including The Nation and The New Republic. These were not the sources typically used when the CIA was subjected to reviews by handpicked friends of Dulles.

The White House adviser completed his memo for revamping the CIA on June 30. He acknowledged that his proposal “implies a fairly drastic rearrangement of our present intelligence set-up.” The basic problem with the CIA, as Schlesinger saw it, was that it was out of control. Under his plan, all future covert operations would be closely supervised by a Joint Intelligence Board composed of representatives from the White House and State Department. In addition, the CIA would be divided into two separate organizations: one for clandestine action, and one for the collection and analysis of intelligence. Furthermore, the agency’s name—a tainted reminder of the Dulles era—would be replaced by “some blameless title,” Schlesinger suggested, like the National Information Service. Kennedy had already made it clear that he was in strong favor of this last recommendation. If he couldn’t raze Dulles’s mausoleum to the ground, he would at least give it a new name.

No stranger to Washington politicking, Schlesinger attempted to rally support for his plan before submitting it to the president, sending copies to Washington power attorney Clark Clifford, veteran diplomat Chip Bohlen, and JFK’s trusted aide and speechwriter Ted Sorensen. By the time the final draft was sent to Kennedy, it was a more complicated and unwieldy document than Schlesinger originally intended. When the Dulles forces, including Taylor himself and the CIA’s congressional allies, immediately mounted a stubborn resistance to the new plan, Kennedy realized that overhauling the U.S. intelligence complex was going to be a much trickier political process than he had hoped. Taylor argued forcefully against the Schlesinger plan, telling JFK “this is not the time for surgery, so far as the CIA is concerned, that it would damage the morale of the employees too much.” Taylor also opposed changing the agency’s name, for the same reason.

On the morning of July 15, Bobby took Schlesinger aside at the White House and told him that the CIA reorganization was on hold until a replacement for Dulles was found. Undismayed, Schlesinger leaped immediately into the hunt for a new director. The president had briefly considered Bobby for the job but realized that his abrasive younger brother would be too politically charged a selection. Besides, RFK was already beginning each morning by dropping by CIA headquarters in Langley on his way to work in Washington so that he could keep an eye on the agency for the president. JFK even raised the possibility of putting Schlesinger in Dulles’s chair. “I imagine that the president was joking,” Schlesinger noted simply in his journal.

Fowler Hamilton soon emerged as the leading candidate for the CIA post. Hamilton had solid credentials as a successful Wall Street lawyer, former prosecutor in FDR’s Justice Department, and a bombing analyst with the Army Air Force during World War II. Schlesinger gave the choice his blessing, telling JFK that Hamilton was a “sober, intelligent, hard-headed lawyer” who “would do the job well.” But there was something about Hamilton that set off the Dulles crowd—perhaps it was simply because he was not one of them. Or it might have been connected to the fact that Hamilton had run the war frauds unit for President Roosevelt and knew too much about the Dulles brothers.

In any case, CIA opposition to Hamilton was so strong that Kennedy decided to abandon him, selecting instead an Eisenhower administration fixture—former AEC chairman, Republican counselor, and military industrialist John McCone.

Now it was Schlesinger’s turn to erupt. Putting an Eisenhower retread in charge of the CIA would be a disastrous move, he warned Kennedy. It would send the wrong signal at the exact moment when the agency needed to be turned upside down. “McCone, for all his administrative qualities, is a man of crude and undiscriminating political views (or to put it more precisely, political emotions),” Schlesinger told the president in a memo. “He sees the world in terms of a set of emotion-charged stereotypes.” But Schlesinger failed to block the announcement of McCone’s appointment in September. Afterward, writing in his journal, Schlesinger tried to cheer himself up, but without much success. “The possibly consoling thought is that the President has a habit of designating ‘liberals’ to do ‘conservative’ things, and vice versa. . . . I am sure JFK knows what he is doing, and possibly my concern here will turn out to be as unwarranted as my concern last December over the appointment of Doug Dillon [as Treasury secretary], but I doubt it.”

In October, still puzzling over McCone’s selection, Schlesinger brought up the subject again with Kennedy in the Oval Office. He asked the president if he knew McCone well. Kennedy admitted that he was not very familiar with his new appointee, but he seemed undisturbed by the prospect of working with him. Kennedy then began to vent about his outgoing CIA chief. “He was very critical of Dulles,” Schlesinger later noted, “and implied that, after Dulles, anyone would do.”

If Kennedy thought that he was getting, in McCone, a respectable Republican front man who would readily do his bidding at the CIA, he was sorely disappointed. In May 1962, Schlesinger fell into conversation at a French embassy party with his friend, banker-diplomat W. Averell Harriman, the old Democratic Party wise man who had served as FDR’s ambassador to Moscow and was now serving JFK as a globe-trotting ambassador at large. Harriman gave Schlesinger an astringent evaluation of the new McCone regime, which he saw as little changed from the Dulles days. This was clear, Harriman confided, from looking at the policy maneuvers around Laos, the Southeast Asia sideshow in which Kennedy was determined not to get embroiled. JFK’s policy of neutrality was being “systematically sabotaged by the military and the CIA,” Harriman warned. “McCone and the people in the CIA want the president to have a setback. They want to justify the [intervention] position CIA took five years ago. They want to prove that a neutral solution is impossible and that the only course is to turn Laos into an American bastion.”

Harriman, a veteran of Washington infighting, then advised Schlesinger how the White House should handle the CIA and military seditionists in its midst. “General [George] Marshall once told me that, when you change a policy, you must change the men too. [The] CIA has the same men—on the desk and in the field—who were responsible for the disasters of the past, and naturally they do things to prove they were right. Every big thing the CIA has tried in the Far East has been catastrophic . . . and the men responsible for these catastrophes are still there.” Kennedy’s purge of the CIA, Harriman made clear, had not been sweeping enough.

The president had lopped off the heads of the top three men at the CIA, but Dulles’s loyal deputies—like Helms and Angleton—were still running the show at Langley. And McCone, a CIA outsider who largely shared the former regime’s views, was more or less content to go along with the old Dulles policies. “McCone has no business in the New Frontier,” Harriman told Schlesinger in March 1963. Dulles’s successor “doesn’t believe in the administration,” said Harriman, and “was full of mischievous ideas and projects.”

Two years into McCone’s tenure as CIA director, syndicated newspaper columnist Henry Taylor published a surprisingly critical piece about the intelligence agency, calling it a “sick elephant” and urging it to “quit stalking through foreign political backrooms and . . . building its own empire.” A few days later, Dulles wrote his old colleague a letter, letting Taylor know that he viewed his column as a personal betrayal and as “a direct attack on me [since] most of what you say [about the agency] happened while I was Director.” Taylor quickly replied with a long, groveling telegram, pleading that nothing he had written—or ever would write—was critical of the spy agency under Dulles’s leadership. “Certainly you must know that any attack on you by me is inconceivable. . . . No one has served this country with greater distinction, selflessness and success than you.” But Dulles made it clear to Taylor that he was still running the show at the CIA, so any distinction the columnist tried to draw between his tenure and McCone’s was false. “Since my retirement,” Dulles told Taylor, “there have been few important policy changes, and I am wholly in support of its new chief and of its recent work.”

This is precisely what Schlesinger was afraid of when McCone took over the CIA in November 1961: that the Dulles era would continue undisturbed. That month, as Kennedy’s special assistant contemplated the new administration’s progress, he could not help falling into a glum mood. Recent conversations with liberal friends and colleagues, he wrote in his journal, “made me face up to the fact that there is no such thing as the New Frontier. We came in last January after a campaign which promised the American people a new beginning [but] we have really done damn little in the way of bold, new initiatives. JFK has given marvelous speeches, but they are almost too marvelous. The words kindle splendid hopes; but the reality remains as dismal as ever.”

Schlesinger grew anxious whenever he began to sense that the old “Eisenhower-Dulles continuities” were “beginning to reassert themselves.” He yearned for Kennedy to break free from the political past, to “ignore the wisdom of the Establishment and accept the implications of his own campaign and his own instincts.” The liberal counselor’s wishes were soon to become true.

By 1962, President Kennedy was challenging the bastions of American power on several fronts, including the corporate elite’s control of the economy. The steel industry crisis that erupted that spring laid bare the growing tensions between JFK and the Fortune 500 circle. On April 6, after yearlong negotiations between steel companies and unions—which involved the personal participation of the president himself—a deal was announced that prevented the rise of steel prices. The steel agreement—which was based on labor concessions that Kennedy administration officials had helped wring from the unions—was a major victory for JFK. The three-way pact hammered out by industry, labor, and government ensured stability throughout the economy, since rising prices in the core industry had been the biggest inflationary factor in the postwar period. “Every time steel prices jump, your pocketbook jumps—with pain,” Estes Kefauver, chairman of the Senate antitrust and monopoly subcommittee, told American consumers in 1959.

But just four days after the Kennedy-engineered steel pact was signed, U.S. Steel chairman Roger Blough scheduled a meeting at the White House and stunned the president by informing him that he was going to announce a 3.5 percent price increase, effective at midnight—a move that would trigger price jumps at other steel companies and send inflationary ripples throughout the economy.

Kennedy was furious at Blough’s double cross, which he correctly saw as a direct challenge to his ability to manage the economy. “My father always told me that all businessmen were sons of bitches,” said JFK at the height of the steel industry crisis, “but I never believed it until now”—a remark that he was happy to have leaked to Newsweek.

While the president saw Blough as a backstabber, Luce’s Fortune magazine regarded the steel mogul as a capitalist hero, declaring him a “business statesman” who was fighting not just for his own company but on behalf of the entire corporate sector by defying the president’s authority. Blough’s company occupied a central position in the country’s corporate pantheon, which was reflected in the U.S. Steel board of directors. Blough himself was well connected within the power elite—including to Dulles, with whom he served in organizations like the Council on Foreign Relations and the Lafayette Fellowship Foundation (part of the Ford Foundation).

Kennedy understood that if Blough and the other colluding steel executives prevailed, his leadership would be severely undermined, not only at home but abroad. He had staked his reputation with organized labor and American consumers on the deal—and now he was faced with “the most painfully embarrassing predicament of his career,” in the view of his White House advisers. A steel industry victory would make it clear to the entire world who ran America.

Determined to protect his presidency, over the next three days JFK unleashed the full powers of the federal government in an all-out effort to crush the steel industry rebellion. Attorney General Bobby Kennedy announced a grand jury probe of steel price-fixing, which he followed by issuing subpoenas for the personal and corporate records of steel executives and by sending FBI agents to raid their offices. “We were going to go for broke: their expense accounts and where they’d been and what they were doing,” JFK’s brother and political enforcer later recalled. “I picked up all their records and I told the FBI to interview them all—march into their offices the next day. We weren’t going to go slowly. . . . All of [the steel executives] were hit with meetings the next morning by agents.” Meanwhile, Robert McNamara’s Defense Department announced that it was reviewing its steel purchasing practices, making it clear that it would favor companies that did not follow U.S. Steel’s price hike.

Kennedy’s strong-arm tactics produced quick results. On April 12, Inland Steel—a smaller but still significant company—caved under the pressure, announcing that it would not raise prices. Bethlehem Steel soon followed, and by the next day U.S. Steel itself waved the white flag.

In victory, JFK adopted a genial and magnanimous posture. Over dinner at the White House on May 3, Schlesinger asked Kennedy what he had said to Blough when the U.S. Steel chairman surrendered. “I told him that his men could keep their horses for the summer plowing,” smiled JFK.

But the resentment from the steel showdown never faded away. Corporate executives continued to snipe at the president, spreading the word that his administration had destroyed “business confidence” by bringing the steel industry to heel. Senator Barry Goldwater, the voice of the rising Republican right, escalated the rhetoric, calling Kennedy’s bare-knuckled tactics against the steel barons “a display of naked political power never seen before in this nation. . . . We have passed within the shadow of police-state methods.”

Chatting with Schlesinger in the Oval Office on June 4, Kennedy said, “I understand better every day why Roosevelt, who started out such a mild fellow, ended up so ferociously anti-business.” JFK vowed that he was not going to appease his big business critics by taking what O’Donnell described as “an ass-kissing posture.” To counter the corporate assault on his presidency, said Kennedy, “[w]e have to put out the picture of a small group of men turning against the government and the economy because the government would not surrender to them. That is the real issue.”

Schlesinger discovered that some of the corporate sniping against the president came from within his own administration. While dining at Joe Alsop’s in late July, the watering hole where Schlesinger kept in touch with the CIA crowd, the White House adviser was disgusted to hear McCone fulminate against Kennedy’s economic policy, which the former industrialist regarded as too pro-labor. “I have rarely seen a man more completely out of sympathy” with the administration’s economic direction, Schlesinger observed in his journal. The CIA director’s “formula for economic stimulus,” wrote Schlesinger, “is to kick labor in the teeth.”

As he continued to wrestle with the disgruntled corporate community into the fall, Kennedy longed to make the battle over the economy the centerpiece of his presidency, telling Schlesinger that he “only wished there were no Cold War so he could debate the future of America with the businessmen.” This is a remarkable and all but overlooked statement, indicating—once again—Kennedy’s visionary thinking.

A year after the April 1962 steel blowup, Kennedy tried to make light of the controversy as he addressed a Democratic fund-raising dinner at the Waldorf Astoria hotel. Told that the steel industry was presenting former president Eisenhower with its annual public service award in another banquet hall at the same hotel, JFK grinned mischievously. “I was their man of the year last year,” he told the Democratic crowd. “They wanted to come down to the White House to give me their award, but the Secret Service wouldn’t let them do it.”

Beset by the rising tensions in his government, Kennedy would bring up the awkward subject of assassination from time to time. In public, as on this occasion, he used it as a comedic device. But in private, with old friends like Red Fay, he mused about it in a more somber vein.

The climate of conflict surrounding the Kennedy presidency had a way of evoking the grim topic. Outraged by the president’s strong stand against the steel industry, Henry Luce invoked the fate of Julius Caesar in a harsh editorial in Fortune, warning JFK that he should “beware the ides of April.” But Kennedy never backed down from his ongoing duel with the steel industry. In October 1963, just weeks before his assassination, JFK’s Justice Department filed price-fixing charges against U.S. Steel and other steel companies, based on Bobby’s earlier grand jury probe of the industry. To the end of his life, Kennedy made it clear that there would be no “ass-kissing” for those corporate powers that tried to undermine his presidency.

After Dulles was ousted by JFK in late 1961, the Old Man’s crowd had quickly closed ranks around him. The Luces immediately offered Dulles succor, inviting Clover and him to spend the New Year holiday at their winter home in Phoenix. Clare Boothe Luce often used the Arizona estate, with its cactus garden and mesmerizing view of Camelback Mountain, to recover from her own bouts of melancholy, dropping LSD with eccentric friends like Gerald Heard, a gay Anglo-Irish writer, devotee of Eastern mysticism, and psychedelic pioneer. Clover found the Luces’ desert refuge a soothing respite from the Washington vortex, but, as she wrote Mary Bancroft from Phoenix, she knew that Allen didn’t share her sentiments: “I do feel an immense relief of burden by Shark’s being out, which he himself doesn’t feel.”

Dulles’s growing sense of resentment toward Kennedy was shared by the Luces, who had known JFK since he was a young Navy ensign. Joe Kennedy had courted Henry Luce’s support for his son during the 1960 presidential race, dropping by the magazine mogul’s Fifth Avenue apartment for a lobster dinner on the final night of the Democratic Convention, and afterward watching TV together as JFK accepted his party’s nomination. “It was a memorable moment in my life,” Luce recalled. “It’s quite a thing to sit with an old friend and watch his son accept the nomination for the president of the United States.”

Luce was not the type to let sentiment cloud his political judgment, however, and he remained loyal to the Republican ticket. But Life magazine, his influential flagship publication, gave Nixon a tepid endorsement, leaving the door open for Kennedy. Luce admired JFK’s intellect and cultural sophistication. But he questioned whether he would be a sufficiently aggressive foe of Communism. After finishing their lobster dinner that night, in fact, Luce had warned Joe Kennedy that he would not stand for it if JFK proved too much of a compromiser in the White House. “If he shows any signs of weakness in general toward the anti-Communist cause, or to put it more positively, any weakness in defending and advancing the cause of the free world, why then we’ll certainly be against him,” Luce told the Kennedy paterfamilias.

The Luce honeymoon with the Kennedy administration had been short-lived. After the Bay of Pigs, Luce’s coverage of the presidency turned increasingly negative. By the spring of 1963, JFK was so exasperated with the relentless drumbeat of criticism from the Time-Life headquarters in New York that he invited the Luces to lunch at the White House to see if he could somehow sweeten the power couple’s disposition. When the press lord launched into a lengthy diatribe on Cuba, demanding that Kennedy invade the island, the president suggested that Luce was a “warmonger” and the afternoon came to an unpleasant conclusion, with the Luces marching out of the White House before dessert was served. Shortly afterward, Luce convened a remarkable war council of his top editors at Time-Life, where he declared that if the Kennedy administration was not bold enough to overthrow Castro, his corporation would take on the task. Luce and his wife were already funding raids on Cuba, with the quiet support of the CIA. Now Luce would escalate his crusade against the Castro regime, in direct defiance of Kennedy.

Like the Time-Life building in Manhattan, Dulles’s brick house on Q Street was a boiling center of anti-Kennedy opposition. The actively “retired” spymaster maintained a busy appointments calendar, meeting not only with retired CIA old boys like Frank Wisner and Charles Cabell, but with a steady stream of top-rank, active-duty agency officials such as Angleton, Helms, Cord Meyer, and Desmond Fitzgerald. More surprisingly, Dulles also conferred with midlevel officials and operational officers such as Howard Hunt, James Hunt (a key deputy of Angleton, and no relation to Howard), and Thomas Karamessines (Helms’s right-hand man). McCone, too, routinely checked in with his predecessor, dining with him and sending him cordial notes.

Though Howard Hunt did not occupy the same social strata as Dulles, the two men were bonded in bitterness: they both felt they had been made scapegoats for Kennedy’s failure of nerve at the Bay of Pigs. The retired spymaster sent Hunt his photograph, and Hunt gave him a copy of his angry Cuba memoir. “I wrote this book as an antidote to the despondency that seized me in the wake of the Cuba project,” Hunt explained in an August 1962 letter, “and I hope it may give you some diversion now.” Serving Dulles, Hunt wrote in an earlier letter, was “an honor I shall always cherish.”

Fearing that his role in the Bay of Pigs fiasco would stall his CIA career under Kennedy, Hunt sought Dulles’s help in starting a new career in the private security field. “It occurs to me that one of your many business contacts might have use for me abroad, particularly if something of my background were known,” Hunt wrote Dulles in August.

Dulles, who told Helms, “I have always thought well of Hunt,” and that he was “disposed” to help him, agreed to get together with Hunt in September. Afterward, Hunt decided to stay in the CIA, while moonlighting as a ghostwriter for Dulles. Hunt was a prolific author and had been churning out spy novels under various noms de plume since World War II. Dulles—who produced four books in retirement, including a war memoir, an intelligence handbook, and two volumes of espionage adventures—also worked on his literary projects with a young former CIA employee named Howard Roman, whose wife, Jane, was employed in Angleton’s deeply submerged counterintelligence unit.

The CIA continued to provide a variety of services large and small for the former director, in addition to supplying him with ghostwriters and research materials. Shef Edwards, the agency’s internal security chief, even stepped in to help Dulles renew his District of Columbia driver’s license in early 1963 so that he could keep cruising the streets of Washington in his aging 1955 Pontiac sedan. Amassing wealth and luxuries had never been important to Dulles, but he did expect to be served and pampered, and the CIA continued to oblige him.

Dulles also stayed in touch with his extensive network of friends and supporters in the U.S. military, who continued to invite him to speak at defense seminars and to play golf on military bases. He lunched with his fellow Bay of Pigs casualty, Arleigh Burke, at the Metropolitan Club. After Kennedy forced him out of the Navy, Burke quickly found another perch in Washington’s far-flung national security complex, becoming chairman of the newly created Center for Strategic Studies at Georgetown University (now the Center for Strategic and International Studies) that he cofounded with David Abshire, a platform he used to publicly air his grievances with the Kennedy administration. Burke made dark allegations about the White House’s “dictatorial” tendencies, charging that his Georgetown offices were the target of a suspicious 1963 break-in.

Rising Republican politicians also sought out the retired spy chief, including a young Illinois congressman named Donald Rumsfeld, who, decades later, would achieve notoriety for his own national security reign. Rumsfeld arranged for Dulles to speak about the CIA and Cuba to the 88th Congressional Club in March 1963, an event the ambitious congressman declared a “tremendous success.”

Cuba remained the source of greatest friction within the Kennedy government. In October 1962, these tensions came close to exploding during the Cuban Missile Crisis, when virtually the entire national security circle around the president urged him to take aggressive actions that would have triggered a nuclear conflagration. JFK’s lonely stand—which was supported only by his brother and McNamara within his inner council—was a virtuoso act of leadership. As the world held its breath, the president painstakingly worked out a face-saving deal with Khrushchev that convinced the Soviet premier to withdraw his nuclear missiles from the island.

Kennedy achieved the compromise by agreeing to remove U.S. missiles from Turkey, which the Soviet Union found equally menacing. In fact, the president had been trying to get the obsolete Jupiter missiles demobilized for over a year but had been stymied by State Department foot-dragging—just one more example of the intransigence and insubordination that bedeviled his administration. JFK was furious when he learned that his original order to remove the Jupiter rockets from Turkey had been ignored. “The President believed he was President, and that, his wishes having been made clear, they would be followed and the missiles removed,” Bobby Kennedy later wrote in Thirteen Days, his memoir about the missile crisis. The President believed he was President . . . it was a striking turn of phrase, one that captured JFK’s uncertain grasp on the wheel of power.

The searing experience of teetering on the nuclear edge had the effect of creating a survivors’ bond between Kennedy and Khrushchev. JFK came to respect the Soviet leader’s earthy wisdom and his surprising eloquence on behalf of peace. “At the climax of events around Cuba, there began to be a smell of burning in the air,” Khrushchev evocatively began a speech he gave a few weeks after the missile crisis, in which he denounced the “militarists” who had sought a nuclear confrontation. Kennedy read aloud part of the speech to Schlesinger, adding, “Khrushchev certainly has some good writers!”

The feelings of respect were mutual. The Soviet leader later said he came to greatly admire JFK during the missile crisis. “He didn’t let himself become frightened, nor did he become reckless,” Khrushchev commented. “He showed real wisdom and statesmanship when he turned his back on right-wing forces in the United States who were trying to goad him into taking military action in Cuba.”

Kennedy’s sincerity in the quest for peace continued to impress Khrushchev the following June, when the U.S. leader gave an electrifying oration at American University, in which he soundly rejected the bellicose assumptions of the Cold War. The address, which would go down in history as the Peace Speech, carried echoes of Khrushchev’s own heartfelt pleas to Kennedy at the height of the Cuban crisis, when he had told JFK that the Russian people were neither “barbarians” nor “lunatics” and they loved life as much as the American people. At American University, Kennedy invoked the same sentiments, in the poetic cadence of speechwriter Sorensen. “We all inhabit this small planet. We all breathe the same air. We all cherish our children’s future. And we are all mortal.”

JFK reinforced his pathbreaking speech by dispatching Averell Harriman to Moscow the following month to hammer out a limited nuclear test ban treaty with Khrushchev—the first diplomatic breakthrough in the struggle to control the weapons race. When the triumphant Harriman returned home, his Georgetown neighbors poured into the street outside his brick town house on P Street to celebrate his achievement. One young woman, who was carrying a baby in her arms, told the old diplomat, “I brought him because what you did in Moscow will make it possible for him to look ahead to a full and happy life.” The crusty millionaire was touched by the effusive neighborhood welcome. Harriman told Schlesinger that by picking him for the mission—instead of one of the usual Cold War envoys—Kennedy had “persuaded Khrushchev that we really wanted an agreement” and were not simply “going through the motions.” Khrushchev had a fondness for Harriman, whom he called “my friend, the imperialist.”

JFK once confided to his friend Bill Walton, “I am almost a ‘peace-at-any-price’ president.” It was a wry reference to the insult that Barry Goldwater, positioning himself for the 1964 presidential race, had begun flinging at political opponents he deemed insufficiently hawkish. By 1963, the military and espionage officials in Kennedy’s government were all too aware of their commander in chief’s dedication to peace—a growing commitment to détente with the Communist world that, in the minds of the national security high command, demonstrated JFK’s naïveté and weakness and put the country at risk. The leadership ranks in the Pentagon and the CIA were convinced that the Cuban Missile Crisis had been the ideal opportunity for Kennedy to finally knock out the Castro regime by launching a full-scale military invasion or even a nuclear broadside. The peaceful resolution of the crisis left Kennedy’s warriors in an ugly mood. Daniel Ellsberg, who later became famous for leaking the Pentagon Papers, observed the seething fury among uniformed officers when he was serving as a young defense analyst: “There was virtually a coup atmosphere in Pentagon circles. Not that I had the fear there was about to be a coup—I just thought it was a mood of hatred and rage. The atmosphere was poisonous, poisonous.”

The anti-Kennedy feelings were particularly virulent in the Air Force, which was under the command of cigar-chomping General Curtis LeMay, who had made his savage mark on history with the firebombing of Tokyo during World War II. The president and the general regarded each other with barely concealed disgust. Twenty-five years after JFK’s death, LeMay and his top Air Force generals were still brooding about Kennedy when they sat down to be interviewed for an official Air Force oral history project. “The Kennedy administration,” LeMay growled, “thought that being as strong as we were was provocative to the Russians and likely to start a war. We in the Air Force, and I personally, believed the exact opposite.”

LeMay and his generals continued to angrily replay the “lost opportunity” of the Cuban Missile Crisis: it was the moment “we could have gotten the Communists out of Cuba,” LeMay declared. “We walked Khrushchev up to the brink of nuclear war, he looked over the edge, and had no stomach for it,” said General David Burchinal, who served as LeMay’s deputy during the crisis. “We would have written our own book at that time, but our politicians did not understand what happens when you have such a degree of superiority as we had, or they simply didn’t know how to use it. They were busily engaged in saving face for the Soviets and making concessions, giving up the . . . Jupiters deployed overseas—when all we had to do was write our own ticket.”

By spring 1963, after two years of turbulence, it was clear that Kennedy was searching for a way to defuse Cuba as an international flashpoint. Abiding by his missile crisis agreement with Khrushchev, the president began to crack down on the anti-Castro raids operating out of Florida and to withdraw funding from the militant exile groups. In April, the leader of the Miami-based Cuban Revolutionary Council, the umbrella organization that tied together the anti-Castro movement, announced his resignation, accusing the administration of cutting a deal with Moscow to “coexist” with Castro. It was now clear that—despite his pronouncements of solidarity with Cuban “freedom fighters”—Kennedy was not serious about overthrowing the Havana regime. This marked the fateful turning point when the rabid, CIA-sponsored activity that had been aimed at Castro shifted its focus to Kennedy.

As Kennedy de-escalated the U.S. campaign against Havana, the violent anti-Castro network of spooks, political extremists, paramilitary adventurers, and assassins went underground. The scheming in hotbeds of exile activity like Miami, New Orleans, and Dallas grew more vicious in the spring and early summer of 1963. Mysterious characters with blood in their eyes began to make their appearance on history’s stage.

One day, Dulles called his former lover, Clare Luce, to warn her about the Kennedy administration’s crackdown on the maritime raids she was helping to finance. “He said to get out of that boat business—he was well aware of it, by the way—because the neutrality act has now been reasserted and it was against the law to aid or abet the Cubans in any attempts to free their country.”

Dulles’s old friend, Bill Pawley, the right-wing Miami entrepreneur who had long collaborated on secret CIA missions, was also warned about his involvement in the exile raids. But he remained defiant, hatching a plot so ambitious that he claimed it would bring down Kennedy himself. In April, Pawley wrote a long letter to his political comrade, Dick Nixon, declaring, “All of the Cubans and most Americans in this part of the country believe that to remove Castro, you must first remove Kennedy, and that is not going to be easy.” Pawley’s plan was to assemble a rogue’s crew of Mafia hit men and Cuban desperadoes and to set sail on his sixty-five-foot yacht, the Flying Tiger II, for the waters off Cuba, accompanied by a reporter and photographer from Life magazine to document the daring mission. Once ashore in Cuba, the raiders were to rendezvous with two Soviet military officers based on the island who wanted to defect, bringing them back to the United States with explosive evidence that Khrushchev had double-crossed Kennedy and had never withdrawn his missiles. The mission went nowhere: there were no missiles or Soviet defectors, and the raiders themselves disappeared, presumably into the jaws of Castro’s security forces.

Years later, two of the mercenaries who had slithered through Miami’s anti-Castro underworld in the early 1960s claimed that the Pawley raid had really been a cover for yet another CIA-Mafia assassination attempt on Castro. The plotting against the Cuban leader continued to flourish, even after the CIA assured the Kennedy administration that it had terminated its alliance with the Mafia. Two emissaries from the CIA informed Bobby Kennedy of the assassination plots at a meeting in his Justice Department office in May 1962. The attorney general, who had built his law enforcement reputation as an aggressive mob hunter, listened to the CIA men with barely contained fury. “I trust that if you ever do business with organized crime again—with gangsters—you will let the attorney general know,” he said with icy sarcasm. The CIA officials assured Bobby that the Eisenhower-approved plots had been shut down—but, in truth, they would continue, without the Kennedys’ knowledge, throughout their administration and for many years after.

The displays of disrespect for President Kennedy’s authority grew more glaring in the clubs and suites of Washington’s permanent government. By the spring of 1963, JFK was painfully aware of the profound miscalculation he had made by appointing Eisenhower-Dulles holdovers and “designating conservatives to do liberal things”—particularly in the case of John McCone. In March, the president’s secret White House recording system picked up a heated conversation between the Kennedy brothers about their increasingly disloyal CIA director. McCone, Bobby informed his brother, was going around Washington feeding anti-Kennedy information to the press. “He’s a real bastard, that John McCone,” responded JFK. “Well, he was useful at a time,” observed Bobby. “Yeah,” replied the president ruefully, “but, boy, it’s really evaporated.”

Meanwhile, Dulles—who had made a show of harmony with the White House early in his retirement, telling friends he would continue to consult with the president—no longer felt a need to keep up the pretense. He became increasingly outspoken in his remarks about Kennedy, despite the earlier reticence he had displayed “for the good of the country.” In June, after delivering a lecture in Cold Spring Harbor, near his Long Island home, Dulles told reporters that he “doubted” he would ever be willing to work again for the Kennedy administration. He also made clear that the president was not serious about ousting Castro. “I don’t know of anything that can be done about Cuba—short of intervention,” he said. “Once a Communist regime gets fastened in a country and the military regime is built up, it’s hard to get that [regime] changed.”

In October 1963, Dulles went public with his most direct criticism of the Kennedy administration in a militant address that he titled “The Art of Persuasion: America’s Role in the Ideological Struggle.” In it, Dulles ridiculed the administration’s “yearning to be ‘loved’ by the rest of the world. . . . No country that wishes to be really popular should aspire to or accept the role of leadership.” The United States was “too rich and too powerful” to be loved, Dulles declared—and that’s the way it must remain.

“I should much prefer to have people respect us than to try to make them love us,” he continued. “They should realize that we propose to remain strong economically and militarily, that we have firm principles and a steady foreign policy and will not compromise with communism or appease it.” Here it was, at last, Dulles’s critique of the Kennedy presidency, in stark relief. JFK was an appeaser, a weak leader who wanted to be loved by our friends and enemies, when the man in the White House should be feared and respected.

Dulles maintained a busy schedule throughout 1963—speaking, traveling, and meeting with an intriguing mix of intelligence colleagues, high-powered friends, and, at least on one occasion, a member of the anti-Castro demimonde. The pages from Dulles’s crowded 1963 calendar that were later released by the CIA contain numerous gaps and blackouts. But, even with the curious blanks, his appointments book has the look of belonging to an active espionage professional who was still fully engaged in a subterranean life. Dulles’s calendar pages and other declassified documents give provocative hints about the retired spy chief’s life, including the identities of some of the obscure characters with whom he was associating. Here was a man, say these pages, to whom people still looked to get things done.

In the summer of 1963, Peter Dale Scott, a young English literature professor at the University of California’s Berkeley campus, found himself in the thick of anti-Kennedy ferment. Scott, the son of distinguished Canadian poet F. R. Scott, a mentor of Leonard Cohen, had served as a Canadian diplomat to Poland, and much of his social life when he arrived in Berkeley revolved around passionately anti-Soviet Polish émigrés. One day, a former Polish army colonel who had befriended Scott invited him to a dinner party at the Palo Alto home of W. Glenn Campbell, the intellectual entrepreneur who built Stanford’s Hoover Institution into a leading center of the conservative resurgence in America. At Campbell’s home that evening, the conversation among the sixteen or so guests soon grew heated as it turned to the man in the White House. “In those days, I was not very active politically, but I was amazed, even shocked, at how reactionary the conversation became around the dinner table,” Scott later recalled. “Most of the talk focused on the danger presented to the nation by its aberrant president, John F. Kennedy. His failure to dispose of Castro, especially during the missile crisis, may have been one of the chief complaints, but it was by no means the only one. The complaints threatened to drag on forever, until one man spoke up with authority. I’m not sure, but he may even have stood up to do so.”

The striking figure who commanded the group’s attention was a Russian Orthodox priest in a dark cassock with a crucifix around his neck. He spoke quietly, but with confidence, assuring the group that they had no need to worry. “The Old Man will take care of it,” he said simply.

At the time, Scott assumed the priest was referring to old Joe Kennedy, who presumably could be counted on to set his son straight. But by 1963, the Kennedy patriarch was confined to a wheelchair after suffering a massive stroke in December 1961 that left him severely debilitated. It was not until years later that Scott realized the Russian priest was more likely referring to someone else. By then, the Berkeley professor was a respected dean of the JFK assassination research community and had devoted years to studying the political forces surrounding the president’s murder. In conversation with a fellow Kennedy researcher one day, Scott was reminded of the nickname by which Allen Dulles was affectionately known in intelligence circles: the Old Man.

On that summer evening in 1963, the Russian émigré priest spoke with the calm assurance of a man who knew something the other dinner guests did not. The Old Man will take care of it. That was enough to calm the heated discussion around the table. The Old Man will take care of the Kennedy problem.

Among the peculiar figures with whom Dulles met in the spring and summer of 1963 was a militant anti-Castro exile named Paulino Sierra Martinez, whose background and affiliations were so murky that even the CIA labeled him “a mystery man” in a memo dated November 20. According to an internal CIA document, Sierra arranged to meet with Dulles and retired Army general Lucius D. Clay in Washington on April 15, 1963. Dulles and Clay were unusual company for a man who, not long before, had been working as a judo instructor in Miami while studying for his law examinations.

Like Dulles, General Clay occupied positions in the top ranks of the American establishment. After serving as the U.S. military governor in postwar Germany, Clay had worked with Dulles in Cold War propaganda projects like the Crusade for Freedom, returning to Germany in 1961 as an adviser to President Kennedy during the Berlin Wall crisis. Clay dangerously escalated the crisis without the president’s authorization by threatening to knock down the recently erected wall with U.S. Army tanks. It took all of the Kennedy brothers’ back-channel diplomatic skills to defuse the confrontation at Checkpoint Charlie. A disgusted Clay later accused Kennedy of losing his “nerve.” By 1963, Clay had given up military service for a corporate career, taking a senior partner position with Lehman Brothers, the Wall Street investment firm, as well as board seats at General Motors and other major companies.

Paulino Sierra Martinez was not the type of man with whom Dulles or Clay normally dined at the Army and Navy Club or the Metropolitan Club. The son of a Cuban police sergeant, Sierra had worked his way up in Havana society, landing a job in dictator Fulgencio Batista’s foreign ministry. But some of his intimates suspected that Sierra’s government post was a cover for his true profession, as a Batista assassin. Fleeing Castro’s Cuba, Sierra settled first in Miami, but after passing his U.S. bar exams, he went to work in the legal department of the Chicago-based Union Tank Car Company, a railroad freight company that had been built by the Rockefeller family. It was in Chicago that Sierra suddenly emerged as a mysterious player in the confusing and conflict-ridden Cuban exile movement.

In May 1963, following his Washington meeting with Dulles and Clay, Sierra—who was virtually unknown in anti-Castro circles—convened a meeting of Cuban exile leaders at the Royalton Hotel in Miami. The leaders were skeptical about the tall, well-dressed man from Chicago, with the long, homely face that put some people in mind of Lincoln. But the anti-Castro movement was in disarray following Kennedy’s withdrawal of support, and Sierra arrived in Miami with an enticing proposal—and the promise of big money to go along with it.

Sierra told the group that he represented an alliance of major U.S. corporations that wanted to regain their lost investments in Cuba. He did not name the companies, but on other occasions he dropped such Fortune 500 brand names as United Fruit, U.S. Steel, DuPont, and Standard Oil. Sierra claimed that these corporations were willing to put up as much as $30 million if the fractured anti-Castro movement could reassemble itself and mount an invasion of the island. He explained that such an operation would not have Washington’s official approval but would be supported by officers within the U.S. military, who would help provide weapons and training bases.

Freely spreading money around, Sierra attracted enough support from within the anti-Castro network to form a coalition he ambitiously titled the Junta of the Government of Cuba in Exile. He crisscrossed the country, drumming up support for the new organization and going on a weapons-buying spree. The sources of Sierra’s funds, which were passed to him through Union Tank Car, remained something of a mystery, although an article in The Miami News indicated that at least some of his money was coming from organized crime lords who were intent on winning back their Havana gambling casinos and prostitution franchises, which before Castro had been a source of enormous underworld profits.

Law enforcement agencies began tracking Sierra as he pursued his shady agenda, but in June the FBI terminated its investigation after concluding that he was involved in nothing more than a “con job.” The Chicago office of the Secret Service, however, suspected that Sierra was a more sinister figure. By November 1963, Chicago—like Miami, New Orleans, and Dallas—had become a nest of anti-Kennedy intrigue. On November 2, local Secret Service officials foiled a well-organized assassination plot against President Kennedy. After landing at Chicago’s O’Hare Airport that day, Kennedy was scheduled to ride in a motorcade to Soldier Field for the annual Army-Navy football game. But the motorcade was canceled after the Secret Service exposed a plot to ambush the president from a tall warehouse building as his limousine slowed for a hairpin turn. The plot, which involved a sniper team composed of a disgruntled ex-marine who worked in the building and at least two Cuban marksmen, bore a disturbing resemblance to the series of events that would claim Kennedy’s life twenty days later in Dallas.

The Secret Service could not connect Sierra to the Chicago assassination plot, but his name did come up in relation to another troubling report. On November 21, the day before JFK’s assassination, a serious threat against the president was made by an outspoken anti-Kennedy Cuban exile leader named Homer Echevarria. While negotiating an illegal arms purchase, Echevarria reportedly said that he had “plenty of money” and would conclude the deal “as soon as we take care of Kennedy.” Sources told the Secret Service that the Echevarria weapons purchase was being financed by Sierra with mob money. After the president’s assassination, the Secret Service planned to pursue an investigation into Echevarria’s threat and the Sierra arms deal, but the agency’s probe was shut down by the FBI after President Johnson gave the bureau responsibility for the case.

Following Kennedy’s death, Paulino Sierra Martinez faded from the front lines of the anti-Castro campaign. Accused by Union Tank Car’s legal counsel of wasting the Junta’s funds, he was eventually replaced as head of the organization. But according to relatives of Sierra, he continued to pursue his underground war against Castro and other left-wing leaders in Latin America. Tough-looking men carrying concealed rifles showed up from time to time at Sierra’s Chicago apartment—men whom one of his children described as “father’s banditos.” Sierra, who frequently packed his own gun, even when taking his young granddaughter to the zoo one day, continued to travel widely well into the 1970s, including to Chile, where he briefly relocated during the CIA-orchestrated unrest that led to the violent overthrow of President Salvador Allende in 1973.

Although Sierra never discussed his hidden life with his son, Paul Sierra became convinced that his father was involved with U.S. intelligence. “I think that personally, Father’s patriotism and hatred for the Communists made him go a little overboard,” the younger man concluded.

More than a dozen years after the Secret Service’s abortive effort to find out more about Paulino Sierra Martinez, the House Select Committee on Assassinations—which reopened the JFK case in the 1970s—again raised questions about Sierra. The sprawling congressional investigation ultimately concluded that Kennedy was the victim of a conspiracy, but it was unable to pin down the identities of those involved or the source of their funds. Committee investigators were intrigued by Sierra’s unsavory connections, including to three sketchy characters who showed up with Lee Harvey Oswald at the Dallas home of Silvia Odio, the daughter of a prominent anti-Castro activist, in September 1963. But, in the end, lacking the time and resources to fully pursue its leads, the congressional panel was forced to acknowledge that the “relevance to the assassination” of Sierra’s activities “remained undetermined.”

At least the House Select Committee on Assassinations tried to shed some light on Sierra and his auspices. The first official inquest into President Kennedy’s assassination—conducted by the Warren Commission in 1964—made no serious effort to examine anti-Castro militants like Sierra and their connections to the CIA and organized crime. Despite the Secret Service’s suspicions about Sierra, his name appears nowhere in the Warren Report’s twenty-six volumes. Allen Dulles, a prominent member of the Warren Commission, could have revealed what he knew about Sierra. But Dulles never brought up Sierra’s name—nor did he ever inform fellow commission members that he had met with someone whom the Secret Service regarded as a person of interest in the Kennedy assassination.

It remains one of the many enduring mysteries of the Kennedy case. Why did Dulles meet with Paulino Sierra Martinez in April 1963? What brought together the former CIA director and an obscure, Mafia-connected, anti-Castro conspirator with a penchant for violent action? As Dulles was keenly aware, organizing a paramilitary operation against the Cuban government was, by the spring of 1963, a violation of Kennedy administration policy and of federal law. By meeting with a character like Sierra, Dulles made it abundantly clear how little regard he had for the president’s authority—and perhaps for his life.

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