The Outfit (60 page)

“Sinatra was an idiot for playing both sides of the field like that,” said D’Amato. “Playing Mooney for a sucker? What, are you kidding me? If he wasn’t so fucking talented, he never woulda gotten away with being such a fink. With the boys, when you let ’em down, you got hit. . . And lie to Sam? Forget it. I can’t think of anyone else who would’ve continued to breathe air after telling a story like the one Frank told to Sam.” Dean Martin agreed, saying, “Only Frank could get away with the shit he got away with. Only Frank. Anyone else woulda been dead.”

On December 6, 1961, the FBI eavesdroppers also caught wind of the escalating warfare between Sinatra and Giancana. On that night, Mooney was meeting in his Armory Lounge headquarters with Johnny Formosa, an underling used as a courier between Chicago and the West Coast, and who occasionally worked at Mooney’s Cal-Neva Lodge.

“Let’s hit Sinatra,” Formosa advised Mooney. Formosa’s rage was such that he relished taking out the entire Rat Pack. “Let’s show those fuckin’ Hollywood fruitcakes that they can’t get away with it,” Formosa said. “I could take the rest of them too - Lawford, that Martin prick, and I could take the nigger and put his other eye out.” The suggestion echoed what the normally restrained Johnny Rosselli had also told boss Giancana. According to FBI wiretaps, Rosselli told Mooney that he should lash out at the those who had broken their word. “They only know one way,” Johnny said. “Now let them see the other side of you.”

But Mooney responded, “No. I have other ideas for them. You call those cocksuckers and tell them I want them for a month or else.”

Giancana’s “other ideas,” which involved having the entire Rat Pack perform gratis at Mooney’s Villa Venice, would take a year to reach fruition. In the meantime, a Chicago associate of Mooney’s named Tommy DiBella learned just how close Sinatra had come to graduating from swing music to “trunk music.” Mooney told DiBella he was considering putting a contract out on the double-crossing singer when he had an erotic epiphany. “[One night] I’m fucking Phyllis, playing Sinatra songs in the background, and the whole time I’m thinking to myself, Christ, how can I silence that voice? It’s the most beautiful sound in the world. Frank’s lucky he got it. It saved his life.”

Sinatra’s reprieve would be, like many of Mooney’s other pronouncements, temporary. In the meantime, Mooney began making plans for Sinatra’s payback for the Kennedy embarrassment.

Giancana’s restraint was surprising, especially given the continued heat being placed on the Outfit by the administration they had helped elect. Bobby Kennedy, clearly not privy to whatever hollow deals his father had cut with the mob, now began to move on Vegas, the very city the Outfit thought it had protected when it had fallen in with Joe Kennedy. Before the Kennedy regime, the
FBI
had managed to tap only the Fremont Hotel. In Vegas, the FBI was now authorized to tap twenty-five telephone lines into Outfit-controlled, or Outfit-invested, casinos such as the Desert Inn, the Sands, the Stardust, and the Riviera. (The phone taps were discovered in 1963 by an engineer for the Fremont, the manager of which promptly enlisted the other casinos in a class action suit against the FBI. The suit was pending until 1967, when the Justice Department indicted them for the skim operation.
⁴
) The noose became so tight for the hoods that they had to put a prohibition on phone conversations altogether. One wiretapped conversation gave evidence of the agony the taps were inflicting on the underworld: Hood One: “I need to get a hold of a guy in Las Vegas, and how the hell am I going to get ahold of him? They don’t even want you to make a call there.”

Hood Two: “You can’t call the state of Nevada. That’s the orders.”

The tireless assault on the underworld did not appear to hamper the Kennedy administration’s efforts regarding the rest of its agenda. Not unlike the overworked Curly Humphreys, Bobby Kennedy continued to burn the midnight oil in his zeal to bring down the number one man on his hit list, Fidel Castro. With the onslaught of millions of pages of recently released government documents, the evidence has become conclusive that Bobby Kennedy, like so many upperworld scions before him, attempted to walk the fine line between moral indignation and utilitarianism regarding associations with the underworld. For in his ardor to remove Castro from the scene, Bobby Kennedy almost certainly approved the ongoing CIA liaisons with Johnny Rosselli and others.
⁵
Years later, Rosselli was asked by a congressional committee if he had ever met the Kennedy brothers during the operation. He responded that the only Kennedy he knew was patriarch Joe Kennedy. Then he postulated that he might indeed have met Jack when he first met Joe. “The only recollection I have,” Rosselli answered, “is I think when they were all kids out in California when his father was running the studio.”

On December 11, 1961, Hoover began a campaign of slow torture against the Kennedy family by first alerting Bobby that Hoover’s hidden mikes had heard all about Giancana’s frustration regarding the double cross in the election deal he had cut with Joe Kennedy via Sinatra. It was just the sort of dirt that Hoover had historically coveted as his own guarantee of job security. He had gathered information on the private lives of powerful people for decades, occasionally letting the subjects discreetly know how vulnerable they were. The Bureau’s head of intelligence at the time, William Sullivan, wrote, “[Hoover] kept this kind of explosive material in his personal files, which filled four rooms on the fifth floor of headquarters.”

Hoover was especially concerned about his purchase with the Kennedy brothers and knew that this was the sort of intelligence that would forestall any attempt to remove him from the FBI. Even before the election, candidate Kennedy had let it be known that he was considering replacing Hoover. “Jack Kennedy disliked Hoover in return,” wrote William Sullivan, “and wanted to replace him as Director.” Now, it appeared, Joe’s dealings had tied the brothers’ hands.

Hoover biographer Curt Gentry powerfully described the charged atmosphere in his book /.
Edgar Hoover: The Man and the Secrets:
“What happened between the Kennedys during the next few days can only be surmised. Robert would obviously warn John that Hoover believed the story (that is, had yet another arrow to add to his quiver), whether it was true or not. Typically, the attorney general would have confronted Joe, certainly to ask about the tale and probably to rant and rave. . . And Robert Kennedy would surely be writhing furiously at this latest twist of Hoover’s thumbscrew.”

Gentry is quick to point out that seven days after Bobby learned of Joe’s campaign shenanigans, and after a likely shouting match between the two, Joe suffered a massive stroke, from which he would never rebound. But Hoover was not yet finished with the education of Bobby Kennedy. In a few weeks, the director would apprise the self-righteous attorney general that he was fully cognizant of more examples of Kennedy family hypocrisy surrounding their dealings with the Outfit.

By the end of 1961, the Castro vendetta had transmogrified into a new joint White House-CIA venture code-named Operation Mongoose, which was typified by open sabotage against Cuba and more tightly held murder plots against its president. The man brought in to oversee this latest variation was a decorated CIA veteran and former FBI agent named Bill Harvey, who openly clashed with the impulsive and inexperienced attorney general over both style and strategy. By this time, Robert Maheu had long since extracted himself from the scheme, and Harvey had no desire to rerecruit him. When Rosselli was later asked about Maheu’s departure from the scene, he explained, “[Harvey] never trusted [Maheu] since his FBI days . . . they were in the FBI together.”

The perceptive Harvey also immediately cut Agency ties to Giancana and Trafficante, both of whom he rightly suspected were conning the White House. By the spring of 1962, Harvey had begun meeting Rosselli in Miami and elsewhere, and with Harvey as the conduit, the CIA passed four poison pills to Rosselli, which he in turn gave to a Cuban exile who promised to get them into Cuba with a team that would administer them to Fidel at the earliest opportunity.

Although he was shirking his Outfit responsibilities in Las Vegas, Rosselli enjoyed the CIA intrigue, and the strong bond he was making with new friend Bill Harvey. Like Rosselli, Harvey was an action man, who defied all bureaucratic refinements that slowed the pace. Both men were also strong patriots with a visceral hatred of all things Communist. Their bond would grow into a lifelong friendship, attested to by Harvey in congressional testimony, and more recently by Harvey’s widow, Clara Grace, or “CG.”

“Rosselli was a very good friend of ours,” CG Harvey recently recalled. “He had dinner in our home.” On those occasions when Rosselli showed up at the Harveys’ Indianapolis home, he always brought gifts for their children, a recurring theme in the childless Rosselli’s life. When the Harveys’ son was in Hollywood, Johnny squired him around, introducing him to movie stars. “He would do anything for you he could possibly do,” CG fondly recalled, “but Bobby Kennedy was hot on his neck.” Although CG Harvey was not naive about the ways of Rosselli’s other life, she made no apologies for her affection for the charming gangster. “I know he had his bad side,” she said, “but he was really doing things on our side that really counted. Bill defended Johnny, saying he was a loyal American. Bill said he would rather ride shotgun with him than anyone else.”

Like Mrs. Harvey, Bill Harvey’s coworkers also became aware of Harvey’s fast-growing bond with Rosselli. An assistant CIA chief of station who worked directly under Harvey recently noted, “Bill was proud of his friendship with Rosselli. He bragged about it. These were guys that got things done, and that appealed to him.”

As their friendship blossomed, Harvey granted Rosselli the privilege of an open door at the massive CIA base in Miami, from where Harvey’s Mongoose raids were coordinated. Throughout the summer of 1962, “Colonel Rosselli,” as he was known at the “JM/WAVE” CIA base, was a part of the Mongoose team, with all the excitement and bunkhouse camaraderie that such an undertaking entailed.

“[Rosselli] had virtual carte blanche into the highest levels of the [Miami] station,” remembers Bradley Ayers, an army captain assigned to the CIA base. “It was clear that somebody had said, you know, give this guy whatever he needs.” Ayers also saw in Rosselli what everyone else had seen regarding his devotion. “There was a quality to Rosselli that came off as the patriotic, true-blue, one hundred percent American. I could see the spark of patriotism there, and I guess that made it all palatable. We were all trying to get the same job done, although we were coming from entirely different places.”

Over many months, Rosselli commandeered V-20 speedboats across the straits to Cuba in dangerous nighttime runs, infiltrating shooters onto the island. On one occasion, his boat was sunk by Cuban patrols, leaving the fifty-seven-year-old gangster to swim hundreds of yards in the cold ocean at night to reach a second boat. On another occasion, a sunk boat forced him into a dinghy, where he drifted for days before being rescued by colleagues who had given him up for dead. For all his devotion, however, Rosselli (and everyone connected to Mongoose for that matter) saw few successes. As time wore on, Bill Harvey began to see the assassination project as not only unwise, but immoral. And Johnny Rosselli had grown weary of the Cuban teams, which seemed far less capable than the hit men with whom he had been acquainted in his other life. According to Harvey’s widow, also a CIA officer with whom her husband spoke freely, Bill Harvey began sandbagging the plots, hoping Bobby would just drop the idea.

At the end of 1962, Bobby Kennedy had drummed Harvey out of Mongoose for what he considered insubordination (Harvey had cursed out Bobby and his brother at a White House meeting). And Rosselli went back to his old life, only to find that the IRS was after him as well. Rosselli’s biographers wrote that he “resented what he perceived as the government’s double-standard - the pressure was increasing at the same time he was risking his life doing Uncle Sam’s dirty work in the Florida Keys.” Rosselli said as much to a Las Vegas associate, elaborating about the influence of Bobby Kennedy. “Here I am,” Rosselli said, “helping the government, helping the country, and that little son of a bitch is breaking my balls.”

The seriousness of the Mongoose enterprise was not without occasional comic relief. One such episode occurred during the summer of 1962, when Curly and Jeanne Humphreys arrived at their Biscayne Bay house after a recent Jamaican vacation. During the island jaunt, Jeanne had learned about how the Jamaicans had imported mongooses to solve their snake infestation problems. Coincidentally, the Humphreys were having a snake problem on their Florida property, and when the pair made a trip to Miami Beach to visit Rosselli at the Fontainebleau, the subject of mongooses was in the front of Jeanne’s mind. Thus, while Curly was upstairs with some of “the boys,” Jeanne remained poolside and made what she thought was innocent small talk with Johnny Rosselli. In doing so, a simple intention to determine what the plural was for
mongoose
turned into a potential disaster for Rosselli. Jeanne remembers the following exchange:

Jeanne: “What do you know about the word
mongoose}”

Johnny (nervously): “Is this a joke?”

Jeanne: “Not to some people it isn’t.”

Johnny: “Are you crazy? This Castro stuff is OK’d by the G. We’re not supposed to talk about it. I can’t believe Curly would talk about such a thing.”

Jeanne: “First, why on earth would Castro be concerned about the snakes in my front yard, and second, I’m the one who told
Curly
about them.”