Biographies & Memoirs


The Pinnacle of Power

Paul Ricca may have been incarcerated, but Humphreys and Rosselli likely felt an occasional twinge of envy, so exhausting was the year 1960. While Curly brainstormed Ricca’s and Accardo’s legal problems, cared for his mentally ill daughter and his grandson, entertained his new young wife, and worked the unions on behalf of Joe Kennedy’s kid (all the while dodging the G), Rosselli was himself pulling overtime out West. This was the period when, according to his biographers, Rosselli “came to preside over every facet of business in the gambling capital.”

For years, the original “Dapper Don” had been brokering complex Sin City financing partnerships - successes that left his associates in awe. “If Johnny Rosselli told [pension fund trustee] Allen Dorfman to go shit on the courthouse steps in Carson City,” said legendary Washington influence peddler Fred Black, “he would shit on the courthouse steps.” When not taking over the lucrative ice machine concessions for all Las Vegas, Rosselli was setting up power lunches in New York for Joe Kennedy. He also assumed hidden control of Monte Prosser Productions, which booked talent into the large local casinos and the worldwide Flilton Hotel chain. Billy Wilkerson, publisher and close friend of Rosselli, wrote in his Hollywood Reporter that the Hilton agreement was “the biggest deal in club entertainment history.” At the same time, Rosselli was overseeing the hiring of the critical casino pit crews and backroom counters, many of whom were sending the skim back to Chicago. Johnny summed up his growing prosperity for a friend over a 1960 dinner conversation: “Everything’s nice and cool. There’s money pouring in like there’s no tomorrow. I’ve never seen so much money.” An FBI informant told the Bureau, “Rosselli was the ’power’ in Las Vegas.”

If Rosselli thought the binding on his day planner could not become more strained, he was wrong. The mob’s ambassador was about to take a meeting with a man who wanted to enlist Rosselli’s services in a secret White House-CIA operation so indelicate that its repercussions would be felt for decades and, in the opinion of many, would inadvertently result in the death of Joe Kennedy’s boy Jack three years after its inception. For the next eight months, the planning of the operation would divert much of Rosselli’s precious time from his Vegas work.

The dangerous enterprise commenced in August 1960, when Rosselli received a call from an upperworld friend living in Beverly Hills named Robert Maheu. A West Coast version of Mario Brod, private detective Maheu would later admit that he had a history of handling “delicate matters” for the Central Intelligence Agency. James O’Connell, deputy to the CIA’s director of security, later testified that he had utilized Maheu “in several sensitive covert operations in which he didn’t want to have an Agency or government person get caught.” After a stint with the FBI in the forties, Maheu formed Robert A. Maheu and Associates (RAMA) and quickly negotiated a monthly retainer as a spy for hire with the CIA. Over the years, the Agency employed RAMA to produce and distribute propaganda aimed at destabilizing enemy states or potentates. Maheu himself admitted to running “impossible missions” for the CIA, many of which were brilliantly researched and reported in Jim Hougan’s 1978 book, Spooks.

Although Maheu often told how he had met Rosselli a year earlier in Las Vegas, Rosselli was adamant in FBI debriefs and Senate testimony that their relationship went back to 1955, when the two were introduced by an L.A. insurance executive named Spitzle. Washington detective Joe Shimon corroborated Johnny’s version, although Maheu’s rendition is admittedly more colorful.1

Regardless of the details of their original introduction, by August 1960, Maheu and Rosselli were, by both men’s admissions, good friends. “My children took to calling him ’Uncle Johnny,’ “ wrote Maheu. Sometime in August, Maheu was contacted by the CIA’s office of security. “They asked me if I’d help ’dispose’ of Castro,” Maheu recently recalled. Maheu was informed by his CIA handlers that the assassination would not take place in a vacuum. “The men from the CIA kept me informed of the invasion plan,” Maheu recently said. “The assassination plot was to take place just prior to the invasion, hopefully.” It seems that some senior CIA officers had met Johnny Rosselli at a Maheu clambake the previous spring and were so taken with the Outfit’s emissary that, when word came to the Agency that Castro was to be removed, the officers immediately thought of “Uncle Johnny.” It is not known if Rosselli had spoken to the CIA boys at the clambake as he had to actor George Raft a year earlier in a Los Angeles bar. When Raft had mentioned that he had just returned from Cuba, where Castro was threatening to take over, Rosselli had bragged, “You give me a couple of guys with machine guns, we could go down there and take over the whole island.” Whatever he had told the CIA officers in Maheu’s backyard, Rosselli left a powerful impression.

There is no way of knowing if Maheu and his Agency contacts were aware that the men pushing the hardest for the CIA operation (to be coincident with an all-out invasion of the Cuban island) were Vice President Richard Nixon and his military aide, General Robert Cushman of the marines. However, other CIA luminaries such as Thomas McCoy, deputy to former CIA director William Colby, knew that Nixon was frantic to add a victory over Castro to his campaign rhetoric before the November election. “It was suggested by various people [in the State Department and the CIA],” McCoy said in 1996, “that there was substantial pressure coming from the White House to get the Cuban thing settled by October 1960 so that this would not be an issue that Nixon had to deal with in the ’60 election.” Another senior Agency man, Tracy Barnes, was confronted by an overworked project officer who asked, “What’s the hurry?. . . Why are we working our asses off on this?” As CIA expert Peter Grose noted, “Barnes had the political savvy to understand that the person pressing the urgency was Vice President Nixon.”

Regarding the planned invasion, Nixon himself wrote in Reader’s Digest four years later, “I had been the strongest and most persistent for setting up and supporting such a program.” The go-ahead for Operation Pluto, the code name for the invasion, was given at a National Security Council meeting on March 17, 1960, just prior to the Maheu clambake. At Nixon’s urging, Cushman met with exiled Cuban militarists’ for the express purpose of implementing the assassination of all Cuban leaders when the invasion, later renamed the Bay of Pigs operation, commenced.2

Either the CIA or Nixon, or both, decided that their liaisons with the unpredictable exiles might not produce the wished-for results. Hence, the overture to Rosselli and the Outfit. As noted, the desired partnership with Rosselli was merely a continuation of a long-secret relationship between the feds and the underworld. However, Maheu was initially taken aback by the unorthodox request for a murder, but after his Agency friends likened Castro to Hitler and told Maheu the action was “necessary to protect the country” and to save thousands of lives, the politically naive Maheu agreed to the assignment, even though it might place his own family in jeopardy in the future.3

The CIA suggested Maheu contact the man they had met at the clambake, hoping that his associates were still enraged at Castro for taking over their casinos. The reluctant assassination accessory agreed to play middleman with the Outfit’s Johnny Rosselli, who agreed to meet for lunch at L.A.’s Brown Derby Restaurant. Surrounded by film people pitching scripts, the two discussed a real-life drama that dwarfed those being advanced by the lunching movie moguls. Without telling Rosselli of the larger invasion plan (he says he never told Rosselli of it), Maheu made his pitch. If Maheu was surprised by the government’s request, Rosselli was positively stupefied.

“Me? You want me to get involved with Uncle Sam?” Rosselli asked.4 “The feds are tailing me wherever I go. They go to my shirtmaker to see if I’m buying things with cash. They go to my tailor to see if I’m using cash there. They’re always trying to get something on me. Bob, are you sure you’re talking to the right guy?” Like Maheu, Rosselli was also initially disturbed by the essence of the request, political assassination. However, after Maheu played the Hitler card, the archpatriot Rosselli agreed to come to the aid of his beloved country - gratis. But as with all serious business, his Outfit bosses would first have to approve. Rosselli wanted verification that this was a government-approved murder plot, and Maheu promised to provide the proof. However, Maheu warned, under no circumstances would the G admit to the partnership, or even the operation. “If anyone connects you with the U.S. government, I will deny it,” Maheu intoned. “I will swear you’re off your rocker, you’re lying, you’re trying to save your hide. I’ll swear by everything holy that I don’t know what in the hell you’re talking about.”

According to Maheu, the appeal to Rosselli’s nationalism clicked. “If this is for the government,” Johnny finally answered, “It’s the least I can do, because I owe it a lot.” Although Maheu offered the Outfit representative a pot load of money, Rosselli declined the offer. Throughout Rosselli’s long involvement with the G’s assassination project, he not only never accepted a dime’s payment, but refused to have his hefty hotel and travel expenses compensated. Among his friends, who learned of the plots decades later, this gesture was no surprise. “He was one of the most patriotic men I ever knew,” remarked one longtime friend. Betsy Duncan Hammes, a Las Vegas singer and longtime Rosselli friend, remembers what Johnny told her after the plots were publicized years later: “He said it was his patriotic duty.”

Despite the denial of support from the feds and the questionable chances for success, Rosselli agreed to take the notion back to his Chicago bosses, and the two friends agreed to meet in New York on September 14 and, hopefully, proceed from there. In Chicago, Mooney Giancana, more concerned with getting a marker on the G than patriotism, made a jest of Johnny’s softheartedness. Detective Joe Shimon, a mutual friend of Mooney and Johnny’s, recalled, “[Mooney] always used to say, ’Give Johnny a flag and he’ll follow you around the yard.’” Of course, patriotism was not the only emotion that stirred in Rosselli; the partnership had practical business benefits. As Rosselli later told a gangster friend, “If somebody gets in trouble and they want a favor [from the G], we can get it for them. You understand. We’ll have the fucking government by the ass.” The idea of getting leverage on the G appealed to Mooney’s innate gangster style, and he seconded Rosselli’s proposal.

Although the Outfit’s low-profile brain trust was skeptical about the Castro plotting, they apparently gave a tentative go-ahead. But Giancana’s puppet masters were not unaware of the downside to Mooney’s new high-profile friends, Sinatra, the Kennedys, his girlfriends Phyllis McGuire and Keely Smith - and now the CIA. On his forays back to Chicago, Mooney Giancana had been crowing about his blossoming relationship with the Kennedys. Columnist Taki Theodoracopulos, who wrote for Esquire, Interview, and other well-known magazines, became close with Giancana as a result of an introduction by Jack Kennedy’s brother-in-law Peter Lawford. Taki recalled, “Sam Giancana was always talking about the Kennedys . . . It was clear that at some point he had met both brothers . . . [Lawford and Giancana] would talk fondly of their shenanigans with the first family . . . they used to talk about the girls Mooney used to produce for the Kennedys. Mooney was proud of it, very proud of his Kennedy connections.”

According to Jeanne Humphreys, Curly and the rest were beginning to worry that both Mooney and Johnny might be putting their growing affinity for the high life ahead of their business sense. “They were starting to call Mooney and Johnny ’starstruck,’” Jeanne recalls. “The fear was that they were getting off on hanging out with Sinatra and CIA guys.” Nonetheless, it appears that the decision was reached to play along if Maheu supplied proof of the government’s authorization for the plot. That proof would be given at the upcoming New York rendezvous.

On September 13, while Johnny Rosselli was en route to his clandestine rendezvous with the G in New York, the G in Chicago was eavesdropping on an important conversation between Curly Humphreys, who had returned from his brief respite in Florida, and Gussie Alex. The agents listened in amazement as Curly spoke of his obtaining the jury pool list for the upcoming Accardo tax trial. The agents had a front-row seat as one of the nation’s great criminal minds gave a seminar on how to succeed in the underworld. “Here’s what we’re gonna do,” Curly said. “After we’ve decided which ones, then we’ll decide how to make the approach.” Alex offered that one potential juror lived in a town where a made guy, Joe Gagliano, had a cousin who owned a gas station. Humphreys then said, “You work on a plan. Do like an investigator would do. Find out if there’s a connection there. Send Gags out there to talk to the gas station guy. Find out how well he knows this woman, then we’ll decide.” Regarding one potential juror, Curly hinted at the power he wielded through Hoffa’s Teamsters: “Now I got a truck driver [juror]. We have an ace there.”

The next day, Rosselli arrived at New York’s Plaza Hotel for his meeting with Maheu. There, Johnny was introduced to Jim O’Connell, the CIA’s chief of the Operational Support Division. O’Connell, using the alias Jim Olds, suggested to Rosselli that Castro be hit in a Capone-style “gangland rubout.” Rosselli quickly disabused O’Connell of the dangerous notion, and the men agreed that poison made more sense. The inclusion of O’Connell was the imprimatur Rosselli needed, and he agreed that he would bring a man with extensive contacts in Havana named Sam Gold to Florida in about ten days, where the team would get down to business. Although he never told Maheu the reason for the timing, it was likely because Sam Gold, aka Mooney Giancana, had other pressing business to address: He was buying into Joe Kennedy’s favorite resort, the Cal-Neva.

It was a perfect deal. Joe Kennedy wanted to demonstrate his seriousness, and Mooney needed a getaway retreat, especially one with the added lure of subterranean passages. On September 20,1960, with Frank Sinatra fronting for him, Mooney purchased stock in the Cal-Neva for approximately $350,000 from Joe Kennedy’s friend Wingy Grober. It has been widely misconstrued that Grober et al. sold the Lodge outright to Sinatra and Giancana. However, a close reading of the application put before the Nevada Gaming Commission reveals that the Sinatra purchasers (Sinatra; his manager, Hank Sanicola; and Dean Martin) only obtained a 49.5 percent interest in the operation, while Grober’s group maintained a 50.5 percent controlling interest. Gaming board member Turner emphasized that “the operation would remain the same, that, in other words . . . the present controlling interest would remain as it is.” Board chairman Milton Keefer added the Sinatra group’s purchase “is not really a transfer, that it is a new acquisition of stock from the present 100 percent operation.” However, if Grober was actually a front for Kennedy, and Sinatra was a front for Giancana, then, in essence, Bobby Kennedy’s nemesis, Mooney Giancana, was now in partnership with Bobby’s father. In an account that echoed the Rix allegation, Peter Lawford’s biographer James Spada reported that Joe Kennedy’s son-in-law Lawford was another of the resort’s many silent partners, a disclosure that has led some to believe that Joe Kennedy staked Lawford in the deal, thus retaining even more interest in the business.

Connected people like Mooney’s future son-in-law Bob McDonnell have known all along of Mooney’s stake in the Cal-Neva. “Mooney Giancana backed Sinatra totally, put up all the money for the Cal-Neva,” McDonnell says emphatically. The FBI also believed that Mooney Giancana was the “silent” owner of the hotel. Rosselli’s friend Betsy Duncan Hammes says emphatically, “I know for a fact that Giancana put the money up for the purchase. Besides, Frank didn’t have that kind of money back then.” One of Mooney’s drivers recently disclosed how he personally took the money from Chicago to Nevada for the transaction.

The allegations of Byron Rix add to the drama of the purchase. If Rix is accurate, then the transfer of Cal-Neva stock to Mooney was Joe’s way of solidifying the deal with the Outfit to back Jack in the election. The secret meeting at the Lodge that year between Joe Kennedy and “many gangsters” may have indeed been, as Rix reported, another reason the hoods decided to support the Kennedy effort. Whereas some in Chicago believed that the reason Mooney brought the Kennedy request to them was a combination of his desire to get a marker on the G, and his groupie mentality toward Sinatra, it now appears that he had a third reason: Joe Kennedy had promised him a piece of the coveted Cal-Neva.

The transfer of Grober/Kennedy stock in the Lodge to Sinatra/Giancana may have been the show of sincerity Mooney and the Outfit needed to fulfill their end of the election bargain. But before that would occur, Giancana and Rosselli moved forward with their participation in Operation Pluto, a scheme that, even if unsuccessful, would ingratiate the Outfit with the Republican candidate, Richard Nixon. It was classic hedge-betting.

On September 24, Rosselli, Maheu, and the CIA’s Jim O’Connell flew separately into Miami, which had been chosen as their logical base of operations. With O’Connell staying at another location, Maheu and Rosselli took adjoining suites at the Kenilworth Hotel. After a few days, “Sam Gold” arrived, and announced to Maheu that the Outfit was now an official partner with the government in its assassination endeavors against Fidel Castro. Gold, the actual Mooney Giancana, immediately moved the trio to the gang’s home away from home, the Fontainebleau Hotel in Miami Beach. There they were ensconced in a five-room suite (with the requisite kitchen) on the penthouse floor. The experience was an eye-opener for Maheu, who had never before experienced firsthand the style and charisma of men such as those from the Outfit. Maheu watched as Giancana had beluga caviar, from a gourmet shop in New York, and champagne delivered daily. The Chicago boss cooked high-cuisine meals while the trio plotted murder. In his autobiography, Maheu described Mooney as dynamic, prideful, and charismatic. “When Sam Giancana walked through the lobby of the Fontainebleau Hotel,” Maheu wrote, “it was like a king passing. People just made way.”

Maheu also bore witness to the other side of Mooney, the side that had seen him succeed on the mean streets of the Patch. The private detective described one exemplary scene at the hotel: “One time, we were all sitting by the pool when a good-looking man walked up and immediately started talking tough. Without even looking at the punk, Giancana grabbed his necktie and yanked him close. Sam stared right into the kid’s eyes and said, T eat little boys like you for breakfast. Get your ass out of here before I get hungry!’ “

Mooney and Johnny soon engaged a third accomplice, who was introduced to Maheu merely as Joe the Courier. Joe was, in fact, Florida Commission member Santo Trafficante, as Maheu would soon learn when he casually perused a Miami newspaper Paradesupplement, which prominently displayed a photo of the Cosa Nostra boss. Maheu was informed that Joe’s cooperation was essential due to his extensive contacts in Havana.

Although an association with the G on official business had its practical benefits, there may have been an emotional component to the Outfit’s acquiescence regarding the plots. Appearing on an ABC News documentary in 1997, Maheu reflected on a subtle expression he noticed in the hoods during his time with them:

Rosselli and Giancana . . . had surveillances on them for years, they’ve known about it. They’ve suspected wiretaps by the federal government, they’ve known about it. And here, out of the clear blue sky, they are asked to help the government. Just think about that as a human being. This perhaps was the biggest compliment that had been paid them since they were in their teens. And I think to a degree that sparked maybe an innate loyalty that they wish had been there or that they had won a war someplace, or that they had been more cooperative with the government. That is the feeling they imbued in me.

Over the next few months, Mooney (Gold), Maheu, O’Connell (Olds), and Rosselli (Rawlston), made frequent return trips to Florida, where they linked up with Santo (Joe) to troll Miami’s “Little Havana,” seeking out exile accomplices. It had been decided to inform the exiles that a group of Wall Street businessmen with nickel interests in Cuba would pay $150,000 for Castro’s head.

In a bizarre irony, the increased surveillance the gang endured in Chicago had followed them to Florida; the FBI was not privy to the Outfit’s secret dealings with the CIA on Nixon’s behalf. It is not known if the hoods noticed their FBI tails, but veteran detective Maheu, who already knew his room phone was tapped, could not help but discern them. “One night at dinner,” Maheu wrote, “I noticed one agent following Rosselli into the bathroom. When Rosselli came back to the table, I went to the men’s room and cornered the operative. I put him in the kitchen.” Maheu was in the awkward position of not being able to disclose the operation to the FBI agents, but at the same time having to let them know they were found out, hoping that they would back off.

When Rosselli made return trips home, he also experienced the paradox. “I had to duck them [the FBI] in order to meet my contacts at the CIA,” Rosselli would later testify. “One day, right in front of the [Los Angeles] Friars Club, I noticed a man. I walked over and opened the car door. He was on the floor of the car. I said, ’What the hell are you doing?’ He said, ’Tying my shoelaces.’ So I took his license number. Then I found out he was an FBI agent. He was there to follow me from the club . . . I told [Maheu] every time I would catch one of those fellows.” And Rosselli showed great bureaucratic insight, later proven accurate, when he guessed at what it all meant. “I was beginning to feel,” he testified, “that this was a pressure on the FBI’s part . . . that they wanted to find out about the CIA.”

Maheu recently commented on the atmosphere, saying, “Here we are, on the one hand, trying to get involved in a project that is presumably in the best interest of the United States government, and our efforts are being jeopardized by another branch of the government.” Maheu decided to let the G in on the scheme. “I made sure that Hoover knew what I was doing,” Maheu recently admitted, “because, from then on, I made all the calls out of the [tapped] suite at the hotel, collect to CIA numbers.” It is not known if Maheu’s suspicion of tapped hotel phones was accurate, but the FBI was certainly beginning to pick up rumblings about the furtive anti-Castro plotting. Just days after his late-September meeting with Maheu, Giancana traveled to New York, where the notoriously indiscreet don bragged to an FBI informant that Castro would be “done away with” before the November election. FBI director Hoover quickly notified, of all people, Richard Bissell, the CIA’s director of covert operations, and one of the small circle aware of the secret assassination efforts. At the same time, Hoover was picking up rumors that gangsters had been seen meeting with unnamed CIA officers in Florida. And on September 26, Hoover fired off a confidential memo to Allen Dulles, the director of the CIA, in which he informed Dulles that Miami-based Cuban exile (and future Watergate burglar) Frank Sturgis had been approached about mounting an operation against Castro. Hoover noted that the memo was classified “confidential” - “since [the] matter concerns a potential plot against the Castro government, the unauthorized disclosure of which could be detrimental to our national defense.” In classic Hoover-esque, the director was letting the Agency know he was wise to the plotting. Any details that had thus far eluded Hoover were soon to be revealed, thanks to Mooney Giancana and his celebrity-chasing.

In late October, Giancana decided to take the measure of Maheu’s loyalty. At the time, the boss feared that one of his best girls, singer Phyllis McGuire, was two-timing him with comedian Dan Rowan, who was appearing at the gang’s Desert Inn in Las Vegas. Giancana told Maheu that either he bug Rowan’s hotel room or he (Giancana) would have to abandon the Castro project and head to Vegas and straighten the matter out, Outfit style. Fearing not only Giancana’s desertion, but the potential for him to tell McGuire what he had been up to in Florida, Maheu agreed to ask a CIA superior, Sheffield Edwards, for advice. “Shef told me that the Agency . . . would pay up to a thousand dollars if I wanted someone to do the job,” Maheu later wrote. Maheu then enlisted a Miami private eye named Ed DuBois to install the bug in Rowan’s room. However, when Dubois’ technician was caught in the act, he told the police, and the FBI, that he had been hired by Maheu.

Eventually, Maheu had to admit to the Bureau the details of his secret plotting with the very hoods Hoover had been struggling to build a case against. Hoover supposedly hit the roof and quickly dashed off a series of memos to all key agencies in an effort to create a paper trail that would absolve the FBI in the event that the CIA’s collusion with the Outfit affected the Bureau’s ability to obtain convictions.

While the quartet worked the Miami streets, in Washington the CIA’s Technical Services Division experimented, often futilely, with nefarious potions for the Miami plotters to somehow have delivered into Fidel’s innards. Simultaneously, members of multiple branches of the U.S. military secretly toiled in Central America in a similarly futile attempt to coalesce a ragtag band of less than two thousand exiles into an effective invasion force. As is well-known now, neither the plotting in Miami Beach nor that in Central America would come to anything even remotely resembling success. But, in one way, that was beside the point, as the original purpose of the exercise was now moot: President Eisenhower refused to green-light the invasion in time for Richard Nixon to benefit in the November election. Now the operation would proceed under its own inertia, albeit with no raison d’etre.

On October 21, while Mooney, Rosselli, and Trafficante plotted with Maheu in Miami Beach, the two presidential candidates were taking stage in New York for their fourth, and final, television debate. Although Jack Kennedy appeared to have bettered Richard Nixon in the previous three encounters, it would soon become apparent to Nixon just how much Kennedy craved a knockout blow in what was still predicted to be a toss-up vote just two weeks off. At this point, virtually all the principals had sullied their hands in the muck of political foul play: Joe Kennedy had sought out numerous gangsters; Lyndon Johnson had obtained the support of New Orleans crime boss Carlos Marcello; for a $1-million payoff, Richard Nixon had jumped into bed with Jimmy Hoffa and his Eastern mob buddies; and even Bobby Kennedy had made a futile approach to Marcello. Now it was Jack Kennedy’s turn to deal from the bottom of the deck.

In the previous two months, candidate Kennedy had repeatedly been briefed on Operation Pluto, the Eisenhower-Nixon secret invasion plan for Cuba.5 It is not clear if Kennedy was also advised of the accompanying assassination planning, currently under way in Miami. Two days before the last debate, Kennedy released a statement to the press that would not only jeopardize the invasion’s chances, but force Nixon to deny the existence of the operation in order to salvage any hope of success. Of course, Nixon’s denial would paint him as “soft on Communism,” exactly what candidate Kennedy wanted - an irony given that Nixon had created his political persona by assuming an arch-anticommunist stance.

“We must attempt to strengthen the non-Batista democratic anti-Castro forces in exile . . . Thus far these fighters for freedom have had virtually no support from our government [italics added],” Kennedy’s statement read. When the debate commenced, Nixon was unable to admit that the “fighters for freedom” were in fact being supported to the hilt by the incumbent administration. Nixon later wrote in his autobiography, RN, “I had no choice but to take a completely opposite stand and attack Kennedy’s advocacy of open intervention in Cuba. This was the most uncomfortable and ironic duty I have had to perform in any political campaign.” In his memoir Six Crises, Nixon added, “For the first time I got mad at Kennedy personally. I thought that Kennedy, with full knowledge of the facts, was jeopardizing the security of a United States foreign policy operation. And my rage was greater because I could do nothing about it.”

The ploy worked, with a Gallup poll showing that viewers, by a 43-23 percent margin, believed Kennedy had won the gabfests. Before one sheds any tears over Kennedy’s treatment of Nixon, it should be remembered that Nixon’s own history of political chicanery is virtually unmatched in American history. Not only did Nixon begin his career by smearing his congressional opponent, Helen Gahagan Douglas, as a Communist, but he conspired with the South Vietnamese to stall the 1968 Paris Peace Talks until after his election6 and authorized virtual terrorism against political opponents in the 1972 contest.

Electing Jack

Back in Chicago, Curly Humphreys geared up for his role in the general-election push. Like his associates in Florida, Humphreys was placed in the contradictory position of carrying out a political function of international consequence while trying to evade the prying eyes and ears of Hoover’s G-men. Once again, Curly gave his wife the choice of whether to accompany him back into the Stevens for two critical weeks in October, adding that this time the work would be even more intense than before. Once again, Jeanne Humphreys chose the luxury of the hotel prison.

Only after the fact did Hoover’s eavesdroppers transcribe a gang conversation that noted Humphreys’ move to the Hilton Hotel. An October 28 report in Flumphreys’ FBI file notes the following secretly recorded recent conversation between Humphreys and underling Hy Godfrey in which Humphreys asked the aide to book him hotel rooms:

Humphreys: “How about this joint down the street?”

Godfrey: “Sheraton?”

Humphreys: “Yeah. See, sometimes it’s easier to get a two-room suite than it is to get one room. Go downstairs and call them. Ask for a one- or two-room suite for a week . . . This time I won’t check in under my own name. The hell with that.”

Godfrey: “Curly, there’s nothing available. Filled to capacity. Went to see [deleted] and [deleted] is there, and his contract is next to him. Also the Hilton [Stevens].”

Humphreys: “Get the Hilton. Get a two-room deal there.”

FBI Summary: “At the conclusion of the above conversation, Godfrey left apparently to get a two-room suite at the Hilton Hotel under a different name.”

The FBI mistakenly surmised that the purpose of the secret Hilton meetings was “to line up prospective witnesses in the defense of TONY ACCARDO.”

The second sojourn at the Stevens became so arduous that Jeanne Humphreys was conscripted into action, helping her husband transcribe his lists. Jeanne quickly noticed that security was even tighter than before, with Phil the maitre d’ personally escorting all visitors to the Humphreys’ suites. The couple’s workday started at six-thirty in the morning and concluded late in the evening. “Votes weren’t bought,” Jeanne wrote about what she overheard. “They were commanded, demanded and in a few cases cajoled.”

The transcribing and cajoling continued for two long weeks in late October. “After I made a legible list, Murray burned his copy,” Jeanne wrote. Although she had no idea what purpose the rewriting served, Jeanne toiled away. “It would have been easier to compile a list of politicians he [Humphreys] didn’t contact or meet with than otherwise,” Jeanne noted in her journal. She sarcastically asked again if she would be placed on the Kennedy payroll. Once again, the familiar names of Wortman, O’Brien, and Olf popped up repeatedly, with a new name added, Jackie Presser. At the time, the Ohio-based Presser was a Cleveland jukebox racketeer, and one of Hoffa’s key Teamster supporters. He would later succeed Hoffa as Teamster president. Curly had given up trying to convince Hoffa to back the Kennedy campaign. Considering all the characters working on bringing out the vote for Kennedy, the ever sarcastic Mrs. Humphreys noted, “It’s ironic that most of the behind-the-scenes participants in the Kennedy campaign couldn’t vote because they had criminal records.”

Watching her husband’s work ethic, Jeanne posed the obvious question: “How can you be so gung ho for something you think is a mistake?” Curly answered, “That’s what I do.” One night, however, Curly’s frustration surfaced as he spoke of Joe Kennedy, whose visage had just appeared on the hotel television. “That old man’s running things,” he said. “It’s his ball game. Mooney’s making a big mistake. Nobody’s going to control those punks as long as he’s alive.” Then, referring to Jimmy Hoffa’s alignment with Nixon, Curly added, “Jimmy’s right, I’m not going to push him [to switch].”

The self-imposed incarceration led to frayed nerves and occasional marital discord. On such occasions, Jeanne abandoned her list-making and stared at the TV. From her journal: “While millions of unsuspecting voters were debating which way to vote, the ’Fixer’ was holed up with a harpie whose only interest was trying to spot Jackie Kennedy in slacks. God Bless America!”

About ten days into the stay at the Stevens, the Humphreys received word from Eddie Ryan that Jeanne’s brother Bob had called on “our (safe) emergency number.” Bob was distraught over recent IRS harassment of Jeanne’s family, not only in Florida, but now also in St. Louis, where Jeanne’s aunt was in tears. Curly told his wife to go and comfort her family, but that she would not be able to return to the Stevens. Curly enlisted Maurie Shanker, one of St. Louis’ top criminal attorneys, to assist his wife’s family. (According to its Humphreys file, the FBI verified five months later Humphreys’ stay at the Stevens/Hilton: “During the fall of 1960, [DELETED] advised that MURRAY HUMPHREYS resided during the latter part of October, 1960, under the name FISHMAN in the Conrad Hilton Hotel in Chicago.”)

In Norman, Oklahoma, Curly’s first wife, Clemi, received a call from her former spouse, with whom she maintained a cordial relationship. After hanging up the phone she turned to their daughter, Luella, and nephew Ernie Brendle. “Father called,” Clemi said. “He and the boys have agreed to support Kennedy. He said to tell the family.” This came as a surprise, since up until this point, Curly had been pro-Nixon. Curly’s niece Brenda Gage recently recalled, “Uncle Lew [her nickname for Curly] said he knew Kennedy would win. He was so sure about it long before the election. Later, I just thought he was so wise to know that.” However, outside the family unit, the fix was to be tightly held.

As the election neared, knowledgeable insiders were tempted to parlay their awareness of the fix into a personal windfall at the Nevada bookie parlors. “I remember going to Vegas that year,” recalls Jeanne. “I told Murray I was going to bet on Kennedy in the election. He became angry, saying I couldn’t do it.” Curly cautioned his young wife, “If we’re seen betting on them, everyone will know what’s going on.” To which Jeanne now playfully adds, “I was only going to bet two dollars anyway.” Joe Kennedy, however, was not so discreet. Legendary sports promoter/ bookie Harry Hall recently said, “I know for a fact that Joe [Kennedy] went to L.A. and put down twenty-two thousand, to win, on his boy,” remembers Hall. “I knew Joe’s bookie. Frank [Sinatra] and Dean [Martin] made big bets also.” Las Vegas historians Morris and Denton located sources that recalled how Jack’s brother Teddy Kennedy had a friend get down an election night $10,000 wager with the Outfit’s Riviera Casino boss, Ross Miller. Hours later, as recalled by oddsmakers such as “Jimmy the Greek,” Teddy apparently enhanced the wager when he had aide Stephen Smith phone up Wingy Grober at the Cal-Neva just before the polls closed and had him lay down an additional $25,000 on brother Jack. All this insider wagering seemed overly bold to the bookies, who rated the contest a virtual toss-up, “six to five, too close to call.”

November 8, election day, brought continued behind-the-scenes manipulations. While Curly labored on the national front, Mooney Giancana worked hard to deliver his key city wards to the Democrats, an effort that not only aided Kennedy, but also worked against crusading state’s attorney Bennie Adamowski. Scores of Giancana’s “vote sluggers” or “vote floaters” hit the streets to “coerce” the voters. Giancana’s biographer William Brashler wrote, “The 1960 Kennedy-Nixon election played into Giancana’s hands . . . the master vote counters of the city’s river wards worked feverishly to deliver their man.” According to G-man Bill Roemer, there is no doubt that Giancana lent his considerable influence to the Kennedy effort. In 1995, Roemer recalled, “We had placed a microphone in Giancana’s headquarters right after the election. There was no question but that Giancana had been approached by Frank Sinatra before the election to help the Kennedys.”

The Outfit bosses were not the only ones working behind the scenes to fix the presidential contest. In Nevada, real estate mogul (and Kennedy insider by marriage to Jack’s wife’s aunt) Norman Biltz was rumored to have imported black voters from out of state, bribing them to cast illegal ballots for Kennedy. Biltz had employed the tactic years earlier when boosting the career of the seminal Nevada senator of the thirties and forties, Pat McCarran. In Texas, Kennedy running mate Lyndon Johnson’s Democratic machine made its own contribution to the 1960 election fraud. Nixon biographer Earl Mazo wrote, “The election shenanigans [in Texas] ranged from ballot-box stuffing and jamming the Republican column on voting machines to misreading ballots cast for Republicans and double-counting those for Democrats.” Mazo points out that in one county, the official tally had 148 for Kennedy-Johnson, and 24 for Nixon-Lodge, although only 86 people voted. The skullduggery proved critical to the Texas outcome, and likely the national tally. In a state where its favorite son should have led the ticket to a huge majority, Kennedy-Johnson managed only a 1 percent edge. It was not the first time Johnson’s clique had been implicated in election fraud.7 And there was more. In Alabama, Kennedy’s popular vote was counted twice, as reported by Neal R. Peirce in his study of the electoral college, The People’s President. If even just the Alabama totals had been accurate, Nixon would not only have won the state, but the nation as well.

From his Massachusetts home, Joe Kennedy continued to work the powerful Daley front via Marty Underwood, a Chicago consultant working for the mayor. Underwood, who would be brought to work in Washington after the Kennedy victory, was originally brought into the fold early on by Kenny O’Donnell as an election adviser. “The old man [Joe Kennedy] wanted to maintain contact with Daley, but didn’t want the phone calls traced,” O’Donnell recalls. “I was dispatched to Minneapolis on election night to route the calls from Hyannis Port to Chicago.” Underwood recently recalled an election night incident in which a Daley aide reported to the mayor that he wasn’t able to retrieve all the “votes” from a Chicago cemetery, as some of the tombstones were overturned. Daley barked, “Well, lift them up, they have as much right to vote as the next person!” Underwood was thus a witness to a ploy that has been recounted by, among others, the longtime JFK friend from Palm Beach, Patrick Lannan. Lannan told author John Davis’ literary agent, “Mayor Daley ’and friends’ went to work stuffing ballots and resurrecting the voters from the dead.” The 1960 election resurrected not just the dead, but an old Windy City proverb: “Death does not mean disenfranchisement.”

It would later turn out that Hoover’s FBI was spying not only on the Outfit, but its friend in the mayor’s office, an undertaking that shed more light on the mayor’s role in the 1960 vote-fraud wars. When Richard Daley’s three-hundred-page FBI file was released in 1997 to the Chicago Tribune, the following passage was included: “on 11/18/60 [DELETED] advised that he had learned from [DELETED] . . . that a Chicago attorney . . . had told [DELETED] that Mayor Daley had paid for thousands of votes in the 11/8/60 election but had not received 25,000 of the votes for which he had paid.”

Like his old friend Joe Kennedy, Los Angeles-based Frank Sinatra maintained an open phone line to Chicago via ward boss and Democratic national committeeman Jake Arvey, a known close friend of Mooney Giancana’s. Arvey updated Frank every half hour on the Chicago tallies.

Back in Washington that night, Washington Post editor Ben Bradlee was at dinner with his friend John Kennedy. He remembered his conversation with the candidate: “Over dinner he told me how he [JFK] had called Chicago’s Mayor Richard Daley while Illinois was hanging in the balance to ask how he was doing. ’Mr. President,’ Kennedy quoted Daley as saying, ’with a little bit of luck and the help of a few close friends, you’re going to carry Illinois.’ Later, when Nixon was being urged to contest the 1960 election, I often wondered about that statement.”

All night long, Illinois, and the nation for that matter, was a toss-up. At eight-thirty on Wednesday morning, Ann Gargan, Joe Kennedy’s secretary, arrived to inform Jack that he had won Illinois. “Who says so?” inquired the exhausted candidate. “Your father says so,” replied Gargan.

As it turned out, the election was so close that without Humphreys’ union work, and the other noted machinations, Richard Nixon would certainly have prevailed. In Chicago, Mayor Daley held back his county’s vote totals until the final tally was received from the Republican-stronghold farm belt in southern Illinois. It was common knowledge that the Republican pols in that region were counting thousands of uncast votes; Daley merely waited to see how many votes he would need to negate the downstate fraud. As the night wore on, Daley calculated that he needed to deliver a 450,000 vote advantage to Kennedy to carry the state; Kennedy took Cook County by 456,312 votes.

When the final count was tallied, out of almost seventy million votes cast nationwide, Jack Kennedy had won by a scant 113,554, less than one tenth of 1 percent of the total, and less even than his margin in just Cook County. Most pertinent, in the states where the Outfit had a strong union presence, Kennedy squeaked to gossamer-thin victories: in Illinois (+.2%), Michigan (+1%), Missouri (+.6%), and Nevada (+1.3%). These states accounted for a decisive 63 electoral votes, which, if given to Nixon, would have changed the outcome (269 were needed to elect; Kennedy obtained 303). With Curly Humphreys’ charges ordered to get out the Democratic vote, which included the all-important ferrying of invalids to the polls, the Outfit’s contention that it “elected Jack” is not without merit.

“I was an airhead,” says Jeanne Humphreys. “I didn’t know that a president could be elected on the whim of Chicago mobsters. In my ignorance, I thought majority ruled.” In Illinois, the next morning’s count showed that Nixon had prevailed in 93 of the state’s 102 counties, yet lost Illinois by 8,858 votes, the result of the large Kennedy majority in Cook County, where Daley and the Outfit turned out a staggering 89.3 percent of the eligible voters, including the eligible deceased. Chicago veteran reporter Walter Trohan asked his old friend Richard Daley about his party’s election shenanigans. “He never denied it,” recalls Trohan. “He confessed that they stole to offset the Republican stealing downstate, which I didn’t believe was on that grand a scale.” Years later, nearing death, Daley told his friend Washington power attorney Edward Bennett Williams, “I have only one question: Will God forgive me for stealing the election from Richard Nixon?”

Of more pressing concern to Daley than even Jack Kennedy’s victory was the simultaneous defeat of Daley’s nemesis, Bennie Adamowski, the threatening state’s attorney. Adamowski’s chief investigator, Paul Newey, recently said, “We were creating bedlam in Cook County, so they knew they had to do something. That election was stolen from Ben - I have no doubt of it.” Three weeks after his defeat, a bitter Adamowski told the Chicago Tribune that more than one hundred thousand votes had been stolen by Daley’s machine.8

With typical sarcasm, Jeanne Humphreys made a notation in her journal that reflected on the decision of the bosses who had outvoted her husband: “Well, the election efforts were a success and the Senate Racket committee was to be disbanded; Bobby Kennedy would kiss and make up with Jimmy Hoffa and all Mooney’s predictions of a respite from crime busters would materialize. What Dreamers!”

After the election, state Republicans conducted an unofficial recount and found that a switch of 4,500 votes in Cook County would have given the state to Nixon and reelected Adamowski. This unofficial recount, which established a gain of 4,539 for Nixon, was prevented from becoming an official tally by Mayor Daley. After Jack Kennedy’s inauguration, a federal grand jury recommended a formal investigation of the vote fraud, but by that time the head of the Justice Department was Robert Kennedy, and the idea had predictably lost favor.

Richard Daley’s help did not go unappreciated by the new president. The day after the inauguration, Daley became President Kennedy’s second visitor to the Oval Office, just after Harry Truman. Daley biographer F. Richard Ciccone wrote, “Of all the Democratic leaders in the nation, only Richard J. Daley had been invited to spend part of Kennedy’s first day in the White House with the new president. Camelot’s king had chosen the first knight for his Round Table.” The Chicago mayor made frequent trips to the White House in the ensuing months, often returning home to find Chicago awash in federal moneys, which led to the great rebuilding of the Chicago highway system. As president, Jack Kennedy appointed numerous federal judges in Chicago and sent many defense dollars Daley’s way. In three years, the city’s main east-west artery, the Northwest Expressway, was renamed the John F. Kennedy Expressway. In stark contrast was the treatment accorded the Outfit for its powerful role in the election, part of a deal struck with Jack Kennedy’s father, Joe.

Morris and Denton described a secret financial fallout from Kennedy’s victory, the bookie payouts: “An unknowing Graham Hollister - a wealthy Sierra foothills Democrat and future official in the Kennedy administration - brought Teddy [Kennedy] his winnings in Los Angeles, guilelessly carrying the cash in a ’brown paper package,’ as one witness remembered. Wingy Grober, it was said, sent the Kennedys their CalNeva winnings in similar wrapping.”

In Chicago, Mooney Giancana was on the top of the world and said to be acting like “a preening peacock” by one associate. “He was really cocky,” said another. On one occasion, Mooney told his and Jack Kennedy’s mutual girlfriend, twenty-six-year-old Judy Campbell, “Your boyfriend wouldn’t be president if it wasn’t for me.” Giancana bragged openly to the bosses that he had “elected” Kennedy, and that the gang would soon see a lessening of governmental harassment, both in Chicago and in Las Vegas. And as an added bonus, Mooney said, the hoods might even get Cuba back.

Giancana’s swagger would have a life span of exactly one month, terminated when Jack Kennedy announced the unthinkable: He was appointing his mob-chasing brother Robert to be the nation’s top law enforcement officer. It became dreadfully apparent to the wisest hoods, such as Curly Humphreys, that the decision to help Joe’s kid get elected would prove to be nothing short of suicidal for the hard-won, forty-year reign of the Outfit. In her journal, Jeanne Humphreys opined about how history would have been different without the Outfit’s participation in the 1960 election: “Nixon would have been elected. No assassinations, no Watergate, and most important to the Outfit, no Bobby Kennedy as Attorney General. The history of the United States from 1960 ’til eternity was made by a mobster from Chicago’s West Side who wanted to impress a crooner from New Jersey.”

1. Maheu said that he had taken on a job to serve a subpoena on the owner of Vegas’ El Rancho Hotel, Beldon Kettleman. The day before traveling to Sin City, Maheu found every hotel booked. In desperation he called old college buddy, and D.C. power attorney, Edward Bennett Williams, who then called Rosselli. Of all places, Rosselli, who had no idea of Maheu’s mission, booked Maheu into El Rancho. “They rolled out the red carpet,” Maheu later wrote. “[My wife] Yvette and I were given a beautiful bungalow, filled with flowers and fruit. And they told us everything was on the house. I was impressed. Johnny must be some kind of miracle worker.” It goes without saying the booking by Rosselli effectively dashed Maheu’s desire to serve Kettleman. When Johnny later found out about Maheu’s awkward position, he “laughed his ass off,” recalled Maheu.

2. Regarding Nixon and the assassination of Castro, the reader is urged to read Anthony and Robbyn Summers’ The Arrogance of Power: The Secret World of Richard Nixon (2000). In 1996, this writer conducted much of the research for the Castro-Nixon portion of that book, which gives ample evidence that Nixon approved the assassination plots.

3. “I had conducted a serious and dangerous assignment on behalf of my government during World War II,” Maheu recently recalled, “living with German agents for two years. And I felt that if I could be responsible in saving lives and that the request was at the behest of my government, I would take it on.”

4. Maheu originally tried to convince Rosselli that the plots were backed by businessmen, but Rosselli cut him off, saying, “I am not kidding. I know who you work for.”

5. For details of the secret Kennedy briefings, see Russo, Live by the Sivord, and Hersh, The Dark Side of Camelot.

6. In 1996, as part of research this author conducted for Anthony Summers’ The Arrogance of Power, the author convinced Anna Chennault to admit her liaison role with Nixon in the secret deal with the South Vietnamese delegation. The book goes into great detail regarding how President Johnson and Vice President Humphrey dealt with the electoral sabotage.

7. Since 1948, Johnson had been pursued by nasty rumors about his ability to create close victories where none existed. In that year, Johnson’s supporters helped erase a twenty-thousand-vote victory by Johnson’s opponent, Governor Coke Stevenson, in the Democratic senatorial primary. For one solid week, new county-by-county totals appeared and turned the election into an eighty-seven-vote Johnson victory. In 1990, Luis Salas, the election judge in Jim Wells County (Precinct 13) admitted to New York Timesreporter Martin Tolchin that under his supervision, and on orders of Johnson confidant and South Texas political boss George Parr, Salas stuffed the “Box 13” ballot with “votes of the dead, the infirm, the halt, the missing, and those who were unaware that an election was going on.” When Stevenson attempted to have the election investigated, he was forestalled when Johnson’s lawyer, Abe Fortas, appealed to the U.S. Supreme Court. Johnson later returned the favor when, as president, he appointed Fortas to the highest court. The Box 13 episode earned Johnson the hated nickname later utilized by Bobby Kennedy to get under his skin, “Landslide Lyndon.”

8. When Adamowski ran for county assessor ten years later, he ripped into the gross undervaluation of the Kennedy’s Merchandise Mart. Although Kennedy friend Cook County assessor P. J. Cullerton set the behemoth’s worth at $16 million, independent studies put the figure closer to $100 million. Deputy County Treasurer Peter Piotrowicz added that as a result of the undervaluing of the Mart and other Loop offices, the residents of Chicago faced a 17 per cent realty tax increase.

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