Paddy Whacked: The Untold Story of the Irish American Gangster (46 page)

If Kennedy did play a role in the woman’s mysterious death, or in the frame-up of Pantages, as Pringle alleged on her deathbed, it’s likely he would have handled the matter in such a way that he’d never be directly implicated. The former whiskey baron and aspiring studio boss cultivated the kinds of relationships he did for precisely this reason: to maintain a reliable buffer zone between the man who gives the order and those who carry it out.

Kennedy’s less-than-distinguished although profitable stint as a movie mogul and producer ended in late 1931, when New York Governor Franklin Roosevelt summoned him to the East Coast to become a key operative in his bid for the presidency of the United States. Coming from a political family as he did, Joe jumped at the chance to establish a direct line to the White House. He personally contributed or helped to raise $200,000 for the campaign—equal to $2.5 million today. According to Timothy A. McInerny, a former
Boston Post
editor who later worked for Kennedy, Joe also served as Roosevelt’s money collector or bag man, arranging for cash contributions from underworld figures and others who wanted to hide their identities. After F.D.R.’s election as president, Kennedy was rewarded with appointments as chairman of the Securities and Exchange Commission, later as chairman of the Maritime Commission, and finally as ambassador to England.

At the same time that Kennedy served in the Roosevelt Administration, he pursued his own business interests. In 1933, through inside contacts in the government, Joe learned that Prohibition would soon be repealed. He immediately began buying up huge quantities of Scotch—fraudulently—by claiming that it was for “medicinal purposes.” The Scotch, mostly Haig & Haig and Dewars, was stockpiled in warehouses near the Canadian border. When Prohibition was finally repealed, Kennedy became overnight the largest single distributor of Scotch in the United States and remained so until 1946, when he sold his interest in Somerset Importers, Inc. for a huge profit.

Following his resignation from the Roosevelt Administration in 1941, Kennedy resumed his relationship with underworld figures in various U.S. locales. In 1943, Joe purchased 17 percent, a controlling interest, of the Hialeah Race Track in Miami, which was frequented by South Florida mob boss Santo Trafficante, Meyer Lansky, and other notable mobsters. Rose Kennedy, in her memoir, wrote of visiting the track with her husband “a couple times a week.” Kennedy was also a regular at roulette tables in Miami Beach carpet joints owned and operated by Lansky during and immediately after World War II. It was also alleged that, through a silent partner, Kennedy purchased a 10 percent interest in the Tropicana Hotel & Casino in Las Vegas, which was co-owned by a consortium of gangsters, including Johnny Roselli, Frank Costello, and New Orleans mob boss Carlos Marcello. And in 1945, with $12.5 million of his own money, Kennedy bought the Merchandise Mart in Chicago, then the world’s largest building and a center of organized crime and corruption in the Windy City.
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The Merchandise Mart, a massive commercial/office building, brought Kennedy directly into the realm of the Outfit, the Chicago-based syndicate that would play such a crucial role in the creation of Las Vegas, the plundering of the Teamsters Union pension fund, and other major post-World War II criminal rackets. Once home to the most renowned speakeasy in the city, Kennedy’s latest purchase was located just north of the Chicago River in the East Chicago Avenue police district, famed for having what senior police officials called a solid setup of corruption. Organized crime controlled the bars, gambling, and prostitution that dominated the area’s economy, as it had back in the days of the old Levee District. It was understood that any illicit business could operate without disruption, as long as two payoffs were made at the beginning of each month—one to the East Chicago Avenue police and one to the local ward committeeman.

Joe Kennedy was nothing if not astute. He knew exactly what he was inheriting when he purchased the Merchandise Mart. He rarely showed his face in the area and didn’t need to. He was now, economically speaking, at the center of a nexus of corruption from which the city of Chicago had derived its very personality. It was a nexus he would come to rely on in later years, especially during the frantic runup to his son John’s landmark election as president.

All the Way With J.F.K.

By late 1944, with too many skeletons in his own closet to attain higher political office for himself, Papa Joe was free to turn his attentions to his oldest living son, John Fitzgerald Kennedy. Known as “Jack” to his friends and family, J.F.K., like his father, had a reputation as a flagrant womanizer. He’d come back from World War II with at least one notorious affair under his belt (with a married Scandinavian journalist and alleged Nazi spy), along with medals for bravery that would eventually become the basis for his bestselling book,
Profiles in Courage
. Upon Jack’s return from oversees, Joe sent him to a well-known Massachusetts political sage to assess his prospects for elective office. “He has poise, a fine Celtic map. A most engaging smile,” reported the sage. Kennedy should “buy him in.”

Joe immediately began plotting the details of John Kennedy’s introduction into the local political landscape. The problem was that Massachusetts, the home base of the Kennedy dynasty, was a highly competitive political universe crowded with veteran incumbents and eager wannabes. Joe quickly determined that the most likely prospect for Jack was to run as the congressman from the 8th Assembly District, which included a couple of Irish working-class neighborhoods as well as Cambridge, home to Joe and Jack’s Harvard alma mater. The district’s current representative, James Michael Curley, was soon up for reelection. A legendary figure in Massachusetts politics for the last four decades, Curley was unbeatable in a one-on-one contest, but Joe Kennedy had other ideas.

The relationship between Kennedy’s family and the most renowned Irish pol in all of Boston history went back at least to the days of Honey Fitz and his tenure as mayor. Curley had blackmailed Fitzgerald into not seeking reelection as mayor in 1914, by threatening to go public with information on his extramarital affair with a woman named Elizabeth “Toodles” Ryan. Curley, who’d once been reelected as ward boss from jail, was as shrewd a hardball politician as ever lived. He merely hinted to the Fitzgerald camp that he was about to deliver a public address entitled, “Great Lovers: From Cleopatra to Toodles.” Fearing public scandal, Honey Fitz stepped aside. Curley went on to serve multiple terms as mayor, governor, and congressman.
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Joe Kennedy knew that Curley’s dream was to be elected mayor of Boston once again. He also knew that Curley, who’d recently had to defend himself in court on various charges of political malfeasance, was deeply in debt. By Curley’s own estimations, he needed somewhere in the neighborhood of $100,000 to run in the city election, which was to be held in November 1945. Curley did not have access to that kind of money. That’s where Joe Kennedy came in.

In November 1944, on the eve of Curley’s reelection as congressman from the 8th District, Kennedy approached Curley with a classic Irish American proposition:
You scratch my back; I scratch yours.
Specifically, Kennedy told Curley that if he agreed to step down from his congressional seat and run for mayor, Joe would pay off his debts, finance his campaign, and even subsidize the salary of Curley’s campaign manager. It was, quite simply, an offer too good to refuse. Curley stepped aside, and Jack Kennedy got himself elected to congress in 1946, serving with a minimum of distinction. In 1954, activating phase two of Joe Kennedy’s master plan, J.F.K. was elected U.S. Senator from the state of Massachusetts.

By the time Joe’s other son, Bobby, became chief counsel for the McClellan Committee, J.F.K. had emerged as an attractive, well-spoken senator with serious potential as a national candidate. Joe the Patriarch, meanwhile, had virtually disappeared from public life. A millionaire many times over (Kennedy’s worth at the time of his death was estimated at $500 million), he was content to stay in the background and manipulate the levers of power on behalf of his offspring. Jack was now the golden boy. In 1956, as a trial balloon, he’d entered his name into nomination as a Democratic party candidate for president and quickly stepped aside when it became clear that Adlai Stevenson would be the party’s nominee. The gesture served the purpose of elevating J.F.K.’s name and face into the national scene, making him appear to be a viable and even likely future candidate. This is why Papa Joe was so concerned about Bobby’s involvement in a potentially embarrassing and dangerous investigation into the activities of organized crime.

The McClellan Committee turned out to be one of the longest and most expensive senatorial investigations in history, lasting over two years, with fifteen hundred witnesses whose recollections (or, at least, recitations of their Fifth Amendment privilege not to testify on the grounds of self-incrimination) filled dozens of volumes totaling over twenty thousand pages of testimony. Most of the dominant mafiosi in America were dragged before the committee, including Johnny Roselli, Carlos Marcello of New Orleans, and, of course, Sam Giancana of Chicago, who smirked at Bobby Kennedy from the witness stand and famously received this retort from the pugnacious chief counsel: “I thought only little girls giggled, Mr. Giancana.”

Bobby’s strongest vitriol was reserved for Teamsters Vice President Jimmy Hoffa, who was short, fiery, and equally as stubborn as Kennedy. The rivalry between the two men was intensely personal, at least on Bobby’s part, which Hoffa could never fully comprehend. Years later, in his own defense, Hoffa commented, “You take any industry and look at the problems they ran into while they were building it up—how they did it, who they associated with, how they cut corners. The best example is Kennedy’s old man…. To hear Kennedy grandstanding when he was in front of the McClellan Committee, you might have thought I was making as much out of the Teamsters pension fund as the Kennedys made out of selling whiskey.”

Throughout the hearings, Bobby Kennedy seemed hell-bent on establishing “the Mafia” as
the
source and instigator of organized crime in America. Mobsters with Italian immigrant roots, in particular, were linked together in a “conspiracy of evil,” as Kennedy called it. One of the more riveting encounters was between the chief counsel and forty-nine-year-old Carlos Marcello, who oozed contempt as he sat in the spacious, high-ceilinged senate hearing room and invoked his Fifth Amendment privilege no less than sixty-six times. Marcello even refused to tell the committee where he was born. Kennedy moved on from Marcello to Giancana and others—badgering, ridiculing, and excoriating them all in his sometimes shrill, Hyannis Port-by-way-of-Harvard manner of speech.

Most Kennedy biographers agree that it is unlikely the aggressive young chief counsel, at this point in his life, knew the full extent of his father’s history with underworld figures. Even so, Bobby’s sometimes obsessive fascination with the Mafia seemed to contain an undercurrent of expiation—as if, by underscoring the fraternal Italian and Sicilian nature of organized crime in America, he was shifting the focus away from others (like his own father) who may have occasionally benefited from or played a role in the underworld’s conspiracy of evil. Bobby’s zeal was undoubtedly inspired by events outside the hearing room as well.

In November 1957, roughly midway through the hearings, an extraordinary event shifted the focus of the committee. In Apalachin, a small town in Upstate New York, local police stumbled onto a large gathering of mobsters at the home of a local resident. The mobsters fled into the woods, where many were caught, rounded up, and held for questioning. The large-scale mobster meeting dominated newspaper headlines throughout the country. Of the fifty-eight men who were detained, fifty had arrest records, thirty-five had convictions, and twenty-three had served prison terms. Eighteen had been involved in murder investigations, fifteen netted for narcotics violations, thirty for gambling, and twenty-three for illegal use of firearms. Clearly, this was not a gathering of the Rotary Club. The conference seemed to suggest something that FBI director J. Edgar Hoover had been discounting for years; there was, in fact, a commission or syndicate of gangsters in the country who met and operated together. The round-up at Apalachin would go down as a landmark in organized crime history and give the McClellan hearings added impetus as part of a vital, straight-from-the-headlines crusade against organized hoodlums.
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As the McClellan Committee finally began to wind down in early 1959, Joe Kennedy was not in the mood to wait around for the dust to settle. His son Jack had already announced his candidacy for the presidency, and there was much to be done. Joe knew that Bobby had ruffled feathers in the underworld, but this was not the time to placate bruised egos or simmering grudges. Joe had been dealing with underworld personalities for decades; he had helped many criminal figures make money through bootlegging, stock scams, and political influence. Now was the time to call in his chits.

In February 1960, Papa Kennedy reached out to his old friend, Johnny Roselli. Through the underworld’s Mr. Smooth, he arranged for a sit-down with a number of high-ranking mobsters to discuss J.F.K.’s candidacy. The gathering took place at Felix Young’s Restaurant in Manhattan. One of the people in attendance was Manhattan attorney Mario Brod, a mysterious figure who had served as a liaison between various mobsters and the U.S. government since the days of Lucky Luciano. Many years after the fact, Brod revealed the details of the Kennedy-mobster powwow to historian Richard Mahoney; he said that many of the New York and Chicago crime bosses whom Kennedy had asked Roselli to invite failed to show up. There were, however, a fair number who did.
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Once the attendees were settled in, Kennedy got right to the point; he asked for a large campaign contribution and, more importantly, for the mob’s help in ensuring that organized labor support his son’s campaign. A number of people at the table objected, reminding the elder Kennedy of son Bobby’s recent high-profile, anti-Mafia crusade. Wrote Mahoney in his book
Sons & Brothers:
“The elder Kennedy replied that it was Jack who was running for president, not Bobby, and that this was business, not politics.”