Paddy Whacked: The Untold Story of the Irish American Gangster (44 page)

The emotional force Papa Joe exhibited when arguing against Bobby’s potentially damaging decision to oversee the McClellan investigation was no surprise to those who knew him—nor was the rigidity of his son’s counterargument. To even his best friends, Bobby was known at times to be a “stubborn bastard.” In the weeks that followed Bobby’s Christmas announcement, Joe enlisted some of his son’s closest mentors and advisers to try to talk him out of it to no avail. Bobby held his ground.

R.F.K.’s decision to proceed as planned caused a rift between father and son that continued over the next two years. The rift was regrettable but expected, given Joe Kennedy’s proprietary interest in seeing J.F.K. ascend to the presidency. Most everyone who knew Papa Joe accepted his argument at face value: He was against Bobby’s involvement in a crusade against organized crime because it would “stir up a hornet’s nest” that might hurt John’s chances. But there was more to this argument than the elder Kennedy was able to fully vocalize at the time.

Papa Joe knew that chasing after mobsters was not like chasing communists, as both Bobby and John had done during the McCarthy hearings. Chasing “Reds” had been like shooting fish in a barrel; communists were social pariahs, with no one to advocate on their behalf. Mobsters, however, tended to strike back. They created corrupt, subterranean alliances that could destroy careers, resorted to violent intimidation, or sought revenge through sensational acts of murder and mayhem.

At the very least, taking on the mob was messy business. Joe Kennedy knew this intuitively and from firsthand experience, not because he read it in a book or heard it through the grapevine. Although very few people, not even members of his own family, were cognizant of it at the time, Joe Kennedy’s rise to power was riddled with potentially compromising underworld alliances. Kennedy had been dealing with mobsters nearly his entire adult life. By and large, they had served him well. He had amassed millions of dollars, in part, by cultivating certain nefarious relationships. Were these relationships to become known, they would destroy the hopes and dreams he had for his family. This was, in effect, Papa Joe’s dirty little secret. For decades, he had been not only the patriarch of an attractive and politically ambitious Irish clan, but also, in a number of interesting ways, the patriarch of the entire Irish American underworld.

Portrait of the Artist as a Young Whiskey Baron

In the nearly forty years since Joseph P. Kennedy’s death in 1969, a more complete portrait of the man’s life has slowly emerged. It has taken this long partly because Kennedy shrouded his personal and professional activities behind a veil of secrecy. Even today, the official record is carefully sanitized. Voluminous FBI records released under the Freedom of Information Act (FOIA) are comprised mostly of innocuous security reviews and fawning letters between Kennedy and FBI Director J. Edgar Hoover. There is no mention of Kennedy’s associations with organized crime figures. FBI communiqués about Kennedy’s links to mobsters have come to light in recent years, leaked to various biographers and investigative reporters, but they are not part of the official file. For a more well-rounded profile of the man, we have a library full of memoirs and remembrances from nonofficial sources, people who knew Kennedy or were directly affected by his actions throughout history.

According to those who knew or did business with the man, Kennedy’s involvement with gangsters began, not surprisingly, with Prohibition. The Kennedy family fortune, which Joe inherited as the oldest son of five-time Massachusetts representative and state senator Patrick Joseph “P. J.” Kennedy, made it possible for the young businessman to dabble in banking and shipbuilding before the onset of Prohibition in 1919. As the full dimensions of the Volstead Act became apparent, enterprising entrepreneurs like Kennedy were in the right place at the right time. With his family fortune and money he made from the stock market, Joe had the capital. He also had the contacts. His father’s political career had been largely financed by the Boston liquor lobby, and his father-in-law, John F. Fitzgerald, was a Boston saloon keeper who rose to become the city’s highly popular mayor and served proudly in local politics from 1892 to 1919.

In accounts of his life, Joe Kennedy is sometimes called a bootlegger, which is not exactly accurate. The term itself comes from old-time moon-shiners hiding flask bottles of whiskey in their boots and refers to the process of distribution. Kennedy was more precisely a rum runner or whiskey baron—an importer and wholesaler. He purchased large quantities of alcohol, mostly Scotch, from England or Canada and facilitated its shipment along Rum Row. The booze was usually transferred from Nova Scotia to the Eastern Seaboard, where it was off-loaded under cover of darkness along the Massachusetts or Rhode Island coastline or somewhere in Long Island, New York. The bootleggers and crime syndicates took over from there. There were literally thousands of bootleggers in operation during Prohibition, but there were very few overseers like Joe Kennedy, who supplied the suppliers and kept up the steady flow of product that made the entire booze racket possible.

The relationships Kennedy forged through whiskey smuggling were the same types of alliances he depended on at various stages throughout his career. In the fledgling movie business, in real estate, and in politics, the scion of the Kennedy clan did not hesitate to utilize the influence of the underworld as an edge in his professional life. He understood how spheres of power interacted in big-city America. Kennedy gained this knowledge at the knee of his father and later from his father-in-law, “Honey Fitz” Fitzgerald, a quintessential Irish pol who sang “Sweet Adeline” at campaign stops and seemed politically invincible until he was forced to relinquish his hold on the mayoralty because of a sex scandal.

In biographies and other accounts of the Kennedy clan, Papa Joe is often described as having been tough and ruthless in his business dealings. In fact, he was probably no more ruthless than the Cabots, the Lodges, and other Brahmin family dynasties of his Boston youth. He was certainly no more ruthless than American industrialists like J. P. Morgan and Henry Ford who used violent strikebreaker squads and labor espionage to keep workers in their places. In the early years of the twentieth century, for a man to rise to a level of corporate esteem, the ability to play hardball was highly valued. What Kennedy also possessed in abundance was an inherent sociability and charm, the byproduct of a vibrant cultural heritage.

Joseph Patrick Kennedy was born on September 6, 1888, at a time when Boston was fiercely divided between New England’s entrenched Yankee aristocracy, the Brahmins, and the growing mass of Irish immigrants who had been flooding into the city since at least the 1840s. Boston, more than any other city, became a center of hostility between native-born Protestants and Irish Catholics. The Know-Nothing Movement achieved its highest level of electoral success in Boston, where church burnings and other acts of intimidation against Catholics were part of the city’s heritage.

The most famous attack was the torching of the Ursuline Convent in 1834. A small group of nuns operated the convent as a boarding school for children of local families. The nuns and children were chased from the building by a Protestant mob, and the convent was burned to the ground. Eight people were eventually brought to trial for the capital offense of arson, but they were all acquitted, a verdict that was greeted with cheers of delight by their supporters. For Irish immigrants throughout the United States and especially in Boston, the burning of the Ursuline Convent and its aftermath was a watershed event in the history of anti-Catholic bigotry.

By the end of the century, the Irish had grown in significant enough numbers to overwhelm the Know-Nothings and ensure that there would be no more church burnings. By 1900, Irish immigrants and Irish Americans represented more than a third of the city’s population and acquired clout in all of the typical areas of employment—police, firefighting, saloons, and politics—but were still relegated mostly to ghetto neighborhoods in the North End, Charlestown, and South Boston.

Joe Kennedy’s father was the son of famine immigrants from County Wexford. Thick and square-shouldered, with neatly-parted brown hair and a luxurious handlebar mustache, P. J. Kennedy had made his way in the New World in the traditional Irish fashion—first as a stevedore on the East Boston waterfront and then as a saloon keeper, from which he launched his political career. After nearly two decades in state politics, he became the city wire commissioner, responsible for electrifying Boston. From there, P. J. went on to infiltrate the most sacrosanct territory of the Brahmins, the banks.

Kennedy’s success as a banker made him rich. With all that wealth, he diversified. Although a lifelong teetotaler, he became the owner of three Boston-area saloons as well as a prosperous liquor importing business that handled shipments from Europe and South America. By the time his oldest son Joe was a teenager, P. J. Kennedy was perhaps the most powerful Irish American in Boston. Even so, young Joe came of age in a city where class divisions were pronounced, not only between the Brahmins and the Irish, but also between the lower-class, shanty Irish and the “two toilet” Irish such as the Kennedys.

The fact that the Kennedy family was more prosperous than most other Irish in Boston but still looked down upon by the WASP establishment engendered a fierce ethnic inferiority complex in Joe that became a guiding principle throughout his life. Kennedy was raised to be an Irish Brahmin; his mother indoctrinated him in the ways of the WASP upper class, insisting that he forego the Catholic school system and attend Boston Latin, a monument to Protestantism with an alumni that included Cotton Mather, Benjamin Franklin, and John Hancock. Kennedy continued his higher education at Harvard University. After graduation, he immediately established himself as young man to watch in the world of high finance. By the age of twenty-five, he was the youngest bank president in the country. In public, he excelled amidst the most entrenched WASP aristocracy in America. In private, with his receding hairline, steely blue eyes, and pronounced Kennedy teeth, he was a Boston Irishman.

Despite his breathtaking upward mobility, Kennedy maintained links with his Irish American roots, mostly through his father-in-law, Honey Fitz. Joe had married Rose Fitzgerald in October 1914, when her father was in the midst of his remarkable political career. Papa Fitzgerald’s reputation as something of a stage Irishman, sentimental and comically verbose, was contrary to Joe Kennedy’s upbringing, but it appealed to his ethnic pride and sense of fun. He also admired his father-in-law’s embodiment of hardball politics, a classic Irish American means to an end involving the use of friendships, political chicanery, and the skillful manipulation of power, of which Joe Kennedy would become an unparalleled master.

In 1918, Joe Kennedy became involved in Papa Fitzgerald’s last winning foray into elective politics. As a key campaign organizer in Honey Fitz’s drive to unseat incumbent Massachusetts congressman Peter F. Tague, Joe acquainted himself with the city’s growing Italian immigrant population. In the Fifth Ward, where the Italians had supplanted an earlier generation of Irish immigrants, Kennedy recruited and paid local paisano to intimidate potential Tague voters. Kennedy achieved his goal; his father-in-law defeated the incumbent by a mere 238 votes. But one year later, after a congressional inquiry into circumstances surrounding the campaign, Fitzgerald was formally accused of voter fraud and his election was overturned.

The repudiation of Honey Fitz was a stinging last blow to the once-vaunted politician, but for young Joe Kennedy the party had only just begun. The Volstead Act made Kennedy a popular man. The earliest recorded example of his ability to slake the thirst of those in need occurred in 1922, two years into Prohibition, when he arranged for the overseas delivery of bootleg Scotch to a Cape Cod beach party, celebrating the ten-year reunion of his Harvard class of 1912. Within the following months, Kennedy organized the importation of another major shipment to Carson Beach in South Boston, believed to be the biggest single shipment of whiskey in Boston Prohibition history.

The profits for Kennedy were staggering. The best Scotch cost $45 a case on Saint-Pierre and Miqueloon, a group of eight, small craggy islands in the North Atlantic Ocean, situated about sixteen miles south of Newfoundland. The cost of shipping along Rum Row added another $10 per case, labor and payoffs perhaps another $10, for an adjusted total of $65 a case—or $325,000 for a typical five-thousand-case shipment. Before it ever reached the marketplace, the Scotch was usually “cut” with other liquids, diluting it by half. It was then rebottled and sold to bootleggers for $85 a case. Thus the net profit for Kennedy on a $325,000 investment could be $525,000: a markup of roughly two-thirds.

How did Kennedy distribute his booze? Over the years, some of the most legendary gangsters from the Prohibition era have given first-hand testimony of their relationship with Joe Kennedy. Frank Costello, in interviews for an autobiography he intended to have ghost-written by author Peter Maas, told the writer shortly before his death that he and Kennedy were “in the liquor business together during Prohibition.” Q. Byrum Hurst, a former Arkansas state senator and a longtime attorney for Owney Madden during his retirement years in Hot Springs, told investigative journalist Seymour M. Hersh, “Owney and Joe Kennedy were partners in the bootleg business for a number of years. I discussed the Kennedy partnership with him many times…. Owney controlled all the nightclubs in New York then. He ran New York more than anyone in the 1920s, and Joe wanted the outlets for his liquor.” The lawyer added that Madden “told me he valued Kennedy’s business judgment. He recognized Kennedy’s brains.”

Kennedy appears to have reached out to Owney and the New York Combine sometime in the mid-1920s, when Big Bill Dwyer was away in jail. That’s why Kennedy found himself dealing with Paul Costello, who was shepherding the operation while Dwyer served his sentence. In numerous Manhattan meetings with Madden, Costello, and Danny Walsh of Providence, the whiskey baron and the bootleggers finalized distribution arrangements. These surreptitious meetings led to speculation that the entire bootlegging racket in the Northeast was led by a group known as the Big Seven—including Kennedy, Madden, Dwyer, Costello, and Walsh.