The most significant and yet least-noticed account of hard evidence tying Kennedy to business dealings with crime figures can be found among the many thousands of pages of testimony on organized crime generated in the early 1950s by the famed Senate hearings chaired by Estes Kefauver, a Democrat of Tennessee. During scores of public hearings across the nation, Senate investigators and local police officials focused on, among other things, the influx of gambling and racketeering in the Miami area prior to and during World War II. One of the most important front men for organized crime in that era was Thomas J. Cassara, a lawyer from New London, Connecticut, who first came to the attention of law enforcement officials in the late 1930s, when he signed a lease as co-owner of the newly constructed Raleigh Hotel in Miami Beach, which was known to have been financed by organized crime families led by Capone’s successors in Chicago and Costello in New York. A few years later, just as World War II was breaking out in Europe, Cassara took over the leases of two nearby hotels, the Grand and the Wofford. Daniel P. Sullivan, a former FBI agent who became operating director of the Crime Commission of Greater Miami, told Kefauver’s Special Committee to Investigate Organized Crime in Interstate Commerce that the area around the Cassara-operated hotels in Miami Beach “became nationally known as a meeting place probably for more nationally known racketeers and gangsters than any one local area in the United States.” The Wofford Hotel, in particular, became the hotel of choice for the criminal elite, Sullivan testified, including Costello, Joey Adonis, Longy Zwillman, and many senior members of the Miami-based organization of Meyer Lansky. This was an era, Sullivan added, when America’s racketeers, hiding their ownership behind men such as Cassara, were pouring “difficult to trace” money into dozens of legitimate businesses, including hotels and nightclubs.
Cassara left Miami in 1941. By 1944, according to testimony before the Kefauver Committee, he was working full-time for Joe Kennedy’s Somerset Importers. The testimony came from Joseph Charles “Joey” Fusco, a former bootlegger and strong-arm man for Al Capone in Chicago. In October of 1950, Fusco was subpoenaed to testify at a closed-door hearing and asked, among other things, about his dealings with Cassara. Fusco replied unhesitatingly: “When he first came to Chicago, I think [it] was in 1944, he was working for Kennedy, the Somerset Import Company. He was their representative here. He used to call on the trade as a missionary man [sic], and that is when I first met Tom Cassara in Chicago. He came into our office and introduced himself. From then on we knew Tom Cassara’s working for Somerset in Chicago. Later on, he opened a company here called the Raleigh Distributing Company. He became one of the distributors with us. In other words, he came in and became a distributor for the Somerset line.” The reference to Kennedy’s company was fleeting, and although the committee understood who Fusco was talking about, Joseph P. Kennedy’s name does not appear in the index to the hearings. Journalists plowing through the voluminous transcripts did not link Kennedy to Cassara or Fusco, and thus the important Fusco reference to Joe Kennedy’s liquor importing business escaped public notice.*
In late January 1946, Cassara was shot in the head, gangland style, in front of a mob-dominated nightspot known as the Trade Winds on Chicago’s trendy Rush Street, an area dominated by nightclubs, bars, and restaurants in the infamous East Chicago Avenue police district, where the hoodlum “outfit” exercised near-total control over illegitimate—and legitimate—business activity. Chicago newspapers identified one of Cassara’s business partners as Rocco DeStefano, but did not report that DeStefano was a first cousin of Al Capone and Joey Fusco. Nor did the newspapers report that Cassara was an employee of Joe Kennedy’s liquor importing business. Cassara survived the bullet wound, the case remained unsolved, and newspaper attention quickly turned elsewhere. Cassara left the liquor distribution business and moved to Los Angeles, where he once again operated as a front man for organized crime families in New York and Chicago.
Joe Kennedy began negotiating his exit from the liquor business within months of the Cassara shooting. On July 31, 1946, he formally sold Somerset to a New York firm controlled in part by New Jersey gangster Longy Zwillman and his longtime Prohibition partner, Joseph Reinfeld.
With that sale, Kennedy cut his last known tie to the liquor business. But few businessmen had his understanding of the intricate relationship between politicians, unions, and organized crime in the major American cities after World War II. Joe Kennedy’s knowledge and contacts would play a major role in the 1960 presidential election, an election stolen, with the help of organized crime, from Richard Nixon.
In 1945 Kennedy bought the Merchandise Mart in Chicago, then the world’s largest building, located just north of the Chicago River, in the East Chicago Avenue police district, and joined the long list of businessmen making monthly payoffs to stay in business. The Mart was famed for its block-long speakeasy, which swung into operation shortly after the building opened in 1930, with no interference by the local police. “The free lunch was magnificent,” New York Times reporter Harrison E. Salisbury recalled in a memoir. “I never knew whether Old Joe owned the bar, but we thought he did and it made someone a lot of money.” One of Kennedy’s former employees, in interviews for this book, said he knew nothing of a Kennedy involvement in the Merchandise Mart speakeasy, but he did recall that Kennedy maintained ownership, at least into the late 1950s, of two old-fashioned Chicago saloons near the Mart that also were within the jurisdiction of the East Chicago Avenue police district.
The district was famed for having what senior police officials called “a solid set-up” of corruption. Organized crime controlled the bars, gambling, and prostitution that dominated the area’s economics, just as it did in Boston’s Fifth Ward. 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, who represented Chicago’s Democratic political bosses. Journalist Sandy Smith, who in the 1980s became the chief investigative reporter for Time magazine in Washington, was assigned to East Chicago Avenue as a police reporter for the Chicago Tribune in 1946. “The mob was so strong,” Smith recalled in an interview for this book. “They had the police department and they had the politicians. If you paid at the beginning of the month, you had a month of immunity.”
Only one FBI document showed a direct link between organized crime figures and Kennedy’s liquor importing business, and it was not among the documents on Kennedy routinely released to journalists by the FBI. In this heavily censored document, part of a 1944 survey of “outstanding mobsters and racketeers” in the Miami area, the FBI reported that a gambler named Charlie Block was “the Southern representative of the Somerset Importers from New York City. He [Block] is known to be a big figure in the liquor industry.” The FBI document added that Somerset was owned by Joseph Kennedy. Block later operated one of Miami Beach’s most popular restaurants, the Park Avenue, in partnership with a professional gambler named Bert “Wingy” Grober, one of Joseph Kennedy’s close friends, who was also heavily involved in Mafia-controlled casinos in Las Vegas. Joe Kennedy’s love for Las Vegas, with its high life, beautiful women, and easy access to political cash, would be shared by his son Jack.
Joe Kennedy’s decision in 1946 to sell Somerset to Longy Zwillman and Joe Reinfeld and get out of the liquor business has been interpreted by some historians as a result of Jack Kennedy’s decision—made with his father’s strong encouragement—to run for Congress that year. “He had enjoyed thirteen profitable years,” wrote Richard J. Whalen, in The Founding Father, a bestselling 1964 biography of Joseph Kennedy, “but the whiskey