Paddy Whacked: The Untold Story of the Irish American Gangster (47 page)

After making his case, Kennedy left the restaurant. The mobsters discussed Kennedy’s overture amongst themselves. Most were lukewarm in their response, but Roselli reminded the men that Kennedy had come to them, which was significant. He asked his associates at least to consider the Kennedy alliance. Meanwhile, the patriarch did not wait around to see if this meeting in Manhattan bore fruit. He was not deterred by the fact that there was resistance due to Bobby’s activities with the McClellan committee. Joe had other names in his mobster rolodex—other fish to fry.

Having studied Jack’s prospects carefully, Joe determined that there were two main areas of concern: the West Virginia primary in May, which J.F.K. desperately needed to win, and the state of Illinois, which would be crucial in the general election. Both were heavy labor states that could be turned around with the right kind of mob support.

In April 1960, Papa Joe invited entertainer Frank Sinatra to the Kennedy compound at Hyannis Port. Kennedy knew Sinatra through his son-in-law, actor Peter Lawford. He also knew that Sinatra had a special relationship with Sam “Momo” Giancana, boss of the Outfit. The Chicago Outfit, through Johnny Roselli, their man in Hollywood, had helped boost Sinatra’s career on numerous occasions. The singer was eternally grateful and even closed his live shows by singing “My Kind of Town (Chicago Is)” as a tribute to Sam Giancana.
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For decades, Sinatra remained mum about his initial meeting with Joe Kennedy, until 1997, when he authorized his daughter Tina Sinatra to give the following account:

A meeting was called [between Joe and Frank]. Dad was more than willing to go. It was a private meeting. I remember it was over lunch…. Dad was ushered in. He hadn’t been to the house before. Over lunch Joe said, “I believe you can help me in Virginia and Illinois with our friends. I can’t approach them, but you can.”

It gave Dad pause…. But it still wasn’t anything that he felt he shouldn’t do. So off to Sam Giancana he went. Dad calls Sam to make a golf game and told Sam of his belief and support of Jack Kennedy. And I believe that Sam felt the same way.

Once Frank Sinatra broke the ice with Giancana, Kennedy took matters into his own hands. Again, it would be many decades before the full extent of his meetings with the mob on JFK’s behalf were fully documented. Gus Russo’s
The Outfit
offers the most detailed account. Russo quotes numerous first-hand sources who were party to a highly secretive meeting between Kennedy and Giancana, which was arranged by a First Ward alderman and circuit court judge William J. Tuohy, one of Kennedy’s oldest friends in Chicago. The meeting took place inside the judge’s private chambers. Behind closed doors, Kennedy made certain assurances that, Bobby Kennedy’s recent history notwithstanding, the election of J.F.K. would benefit Giancana and his friends. Certain known mob figures currently facing legal and/or deportation problems would see those problems disappear. “Any administration led by the Kennedy family will be good for your people,” Joe assured Sam.

Given the way Giancana had been ridiculed by Bobby Kennedy during the McClellan hearings, the mobster had every right to be skeptical. But he was apparently dazzled by the Irish patriarch; in later months, he was often heard bragging that he was “trying to get that Joe Kennedy’s kid elected president.”

There were other meetings that summer, most of them held covertly at the Cal-Neva Lodge, a luxury resort that straddled the California-Nevada state line on the north shore of Lake Tahoe, a region known as Crystal Bay. In this bucolic setting, described in brochures as “Heaven in the High Sierras,” Kennedy maintained a series of bungalows that became headquarters for the unofficial Kennedy campaign braintrust. It was a short hop by plane from Cal-Neva to Las Vegas and on to Chicago, which became a well-worn path for Joe, Sinatra, Giancana, and others involved in a subterranean effort to ensure J.F.K.’s election as the country’s first Irish Catholic president.

In hindsight, Giancana’s willingness to trust Joe Kennedy and go to bat for his offspring may seem inexplicable. Many people in Giancana’s own organization told him he was crazy. Murray Humphreys, a high-ranking member of the Outfit who remembered Joe Kennedy from his bootlegging days, bad-mouthed Kennedy as an untrustworthy “four-flusher” and a “potato eater.” Others told Giancana he was putting his neck on the line by working for the Kennedys after Bobby’s excoriation of “our friends.” Some mobsters flatly refused to help with Kennedy’s election in any way, most notably Carlos Marcello in New Orleans, who later made a personal cash contribution of $500,000 to the campaign of Kennedy’s rival, Richard Nixon. The money was picked up in New Orleans and delivered to the Nixon campaign by another avowed Kennedy hater, Teamster boss Jimmy Hoffa.

But Momo Giancana had his reasons. An underworld traditionalist, his motives for cooperating with Joe Kennedy were rooted in a tacit agreement between certain Italian underworld figures and Irish Americans that had been in effect since at least the big Atlantic City conference of 1929. That conference had established new ground rules by redefining the role of the Irish in the eyes of Italian and Jewish racketeers. Irish mobsters were shut out or killed, nowhere more so than in Chicago, where young Sam Giancana had established a reputation as a fierce gangster described in one police report as “a snarling, sarcastic, ill-tempered, sadistic psychopath.” Giancana started out as member of the 42 Gang, a notorious Italian street gang, and eventually caught the attention of Al Capone, who enlisted the young gangster’s services as a wheel man. Giancana became a key player in the mob’s hostile takeover of Irish American bootlegging operations, forcing many would-be Irish crimesters to seek refuge in ward politics and police work, which is exactly where the Syndicate wanted them.

By forcibly assigning the Irish this role, the Italians accepted as a quid pro quo that they at least listen when approached by an Irish American politician, lawman, or businessman looking to play along with the mob. After all, the Irish had arrived before everybody else and infiltrated mainstream society in a way the Italians and Jews had not. Their function was to hatch schemes from the inside, which is exactly what Joe Kennedy was offering Sam Giancana. Kennedy was dangling the prospect of an inside track on American political and business affairs unlike anything the Syndicate had ever experienced before. How could Sam Giancana say no to such an offer?

The truth of this hypothesis is to be found in the way Giancana dutifully carried out Kennedy’s wishes, as if he were fulfilling an obligation that was at the very heart of the mob’s multiethnic agenda. Giancana didn’t just agree to go along with Kennedy’s plan; he leaned on others in the underworld to do so also, mortgaging his own reputation on the alliance with Papa Joe.

The first order of business was to guarantee Jack Kennedy’s victory in the upcoming West Virginia primary, thus proving the candidate’s electability even in rural, non-Catholic regions of the country. Overnight, mob-controlled juke bosses throughout West Virginia began featuring J.F.K.’s campaign theme song, a reworded version of Sammy Cahn’s current hit “High Hopes,” sung by Sinatra. A Kennedy aide traversed the state (one of the poorest in the United States), paying tavern owners twenty dollars each to play the song repeatedly.

Money began to fall out of the sky. Suitcases full of cash were delivered by silk-suited men named Vinnie, Tony, and Rocco. As FBI wiretaps would later disclose, Sinatra and Giancana’s close friend Paul “Skinny” D’Amato spent two weeks in the state dispensing $50,000 worth of contributions, most of it in the form of desks, chairs, and supplies for politicians around the state. According to D’Amato, Joe Kennedy even paid him a personal visit and, in exchange for his help in the campaign, promised that, if elected, his son Jack would allow deported New Jersey mobster Joe Adonis to return to the United States. This was just one of many Joe Kennedy promises to the mob that would go unfulfilled.

J.F.K. won in West Virginia and went on to secure the nomination by August. By all indications, the general election that fall was going to be close, with Nixon and Kennedy neck-and-neck in most polls. Every vote would count. Just as Joe Kennedy had predicted, it looked like the race was going to come down to the state of Illinois. The Kennedy patriarch would pull out all the stops.

There were continued meetings with Giancana, at least one of them arranged by Mayor Richard Daley of Chicago. In the long history of Irish American political bosses, Daley was truly the last of his breed—a quick-tempered, salt-of-the-earth product of the Chicago Machine who was fiercely proud of his working-class Irish roots. “Da Mare” had known Joe Kennedy for years. Having come from opposite ends of the Irish American spectrum—Kennedy, the Irish WASP by way of Harvard, Daley, the aggrieved proletarian from blue-collar Bridgeport—their relationship was based more on political expediency than friendship. Kennedy cultivated the mayor to be his Irish lackey, and Daley soaked Kennedy for campaign cash. They met occasionally for lunch at the patriarch’s Merchandise Mart, no press allowed.

At the Ambassador East Hotel in downtown Chicago, over the course of three meetings, Kennedy, Daley, and Giancana discussed strategy. It was agreed that certain key districts, including the First Ward, would be delivered on election day by large pluralities. Mayor Daley, through the Chicago police department, would make sure there was no outside interference.
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On election day, November 8, 1960, everything fell into place. J.F.K. won by the slimmest margin in history, with the key districts in Chicago proving to be the margin of victory. The election was a classic Machine-style effort. Subterranean Irish and Italian criminal forces coalesced as they had in many old-style city, county, and state elections since the birth of the American underworld. In many ways, it was a replay of the election Joe Kennedy had engineered for his father-in-law, Honey Fitz, way back in 1918. Only this time, Papa Joe had outdone himself by making grandiose promises to the powerful underworld figures who had dutifully followed his every command. These were not men to be taken lightly. Now that they had done what was asked of them, they expected to see results.

The Kennedy Double Cross

The first shocker came with J.F.K.’s naming of his attorney general. The appointment of brother Bobby as the nation’s top cop had come at the insistence of Papa Joe, who saw the choice as a fait accompli. Joe must have known that Bobby’s appointment would not sit well with Giancana, Roselli, and the rest of the boys, but he was faced with an even more pressing concern. J. Edgar Hoover had come to Joe immediately after J.F.K.’s election with the startling information that Jack had been carrying on an affair with a woman named Judith Campbell (later Judith Campbell Exner), who was at the same time having an affair with Sam Giancana. Hoover claimed to be concerned that the president, at the very least, was opening himself up to potential blackmail. Joe Kennedy was concerned that Hoover would hold this information over the president’s head. The elder Kennedy believed Bobby’s appointment as attorney general would provide an essential buffer that would protect J.F.K. from internal government attack from the likes of J. Edgar Hoover.

Bobby Kennedy undertook his role as attorney general with the same kind of zeal he had exhibited during his stint with the McClellan Committee. In fact, at his first press conference under his new title, Kennedy announced that dismantling organized crime would be the Justice Department’s highest priority, and added that he had his brother’s full support in the effort.

Kennedy’s actions were swift and unprecedented. The number of attorneys in the Department’s Organized Crime and Racketeering Section ballooned from seventeen to sixty-three; the number of illegal bugs and wiretaps grew from only a few to more than eight hundred nationwide; Bobby drew up a hit list of top mob targets—a list that included Johnny Roselli and Sam Giancana, the very men whom Papa Joe had leaned on to get J.F.K. elected. To the gangsters, Bobby’s antimob initiative was inexplicable and seemed highly personal in nature. Among the many acts undertaken by the Kennedy Administration that rocked the underworld were

1. The “kidnapping” of Carlos Marcello:
Tops on Bobby’s mafiosi hit list was New Orleans crime boss Carlos Marcello, who had defied Bobby during the McClellan hearings and, as Kennedy later learned, made a secret $500,000 contribution to the Nixon campaign through arch-enemy Jimmy Hoffa. On April 4, 1961, under pressure from the Justice Department, Marcello was literally snatched off the streets of New Orleans by federal agents, put in an airplane, and flown to Guatemala, where he was summarily deported under the pretext of traveling under a false passport.

Outraged to the point of hysteria, Marcello snuck back into the United States two months later and filed suit against Attorney General Robert Kennedy. At the same time, he apparently tried to broker a truce. According to author John H. Davis in
Mafia Kingfish
, an FBI wiretap picked up a conversation between two well-known northeastern mob bosses about how Marcello had tried to use Frank Sinatra to help get Bobby Kennedy off his back. Sinatra was successful in getting Bobby’s ear, but the overture only made matters worse. Instead of getting Kennedy to take it easy on the Louisiana mob boss, the stubborn attorney general, suspecting perhaps that his father had put Sinatra up to it, stepped up his efforts against Marcello. The U.S. government reinitiated criminal proceedings against the mafioso on charges of conspiracy in falsifying a Guatemalan birth certificate and committing perjury. Marcello’s brother also was indicted.

Down in New Orleans, the volatile Marcello seethed and cursed the Kennedy name, telling anyone who would listen, “You just wait; you wait an’ see if that son of a bitch Bobby Kennedy is gonna take me away from my wife an’ kids.”