The Outfit

by Gus Russo

  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 Parade supplement, 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 S
t. 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.”