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.
The most far-reaching member of this group, purely from a business standpoint, had to be the Man from Boston. Having come from the most intensely parochial Irish city in the United States, Joe Kennedy was not content to settle for local success, either in his home state of Massachusetts or even in the entire Northeast. Kennedy’s vision, which he applied to his life, his career, and later to the lives of his children, was breathtakingly audacious for a man from Irish Catholic immigrant stock. As a corporate entrepreneur, he was always looking for ways to expand and increase profits, which, in the bootlegging business, inevitably led him to Al Capone.
In 1926, Capone was firmly entrenched as the bootlegger boss of Chicago and much of the Midwest. He’d rubbed out Dean O’Banion and taken over his lucrative North Side territory, expanding into the Illinois suburbs and even adjoining states like Indiana, Missouri, and Wisconsin. Kennedy wanted Big Al’s business. Allegedly, the two men met over dinner at Capone’s home in Cicero. The meeting was seen and overheard by a young piano tuner named John Kohlert. Capone was a jazz lover who sometimes invited musicians to his place for jam sessions after the clubs closed. He had Kohlert keep his piano tuned on a monthly basis. On this particular night, the young man was invited to stay for a spaghetti dinner, which was attended by Kennedy. The young piano tuner listened while Kennedy and Capone struck a deal wherein Capone traded his whiskey for a shipment of Kennedy’s Seagram’s brand. The exchanges were to be made in Lake Michigan, off Mackinac Island.
Kennedy’s role as a supplier for Capone’s syndicate is further documented in The Outfit, author Gus Russo’s thorough delineation of the Chicago underworld from Prohibition to the present. Russo unearthed records of a 1926 Canadian government investigation into Canadian alcohol being exported to the United States, primarily by way of Detroit and Chicago. At the time, Canadian authorities were trying to discern how much export tax they were owed by the American bootleggers.
The commission’s paperwork showed that the one purchaser whose name appeared time and again was Joe Kennedy; he had been buying up liquor from Canada’s Hiram Walker facility, which had upped its production 400 percent to meet Kennedy’s demand. In the same Hiram Walker record book was the name of Al Capone and other U.S. “partners” of Kennedy’s.
The extent to which Kennedy profited from this arrangement was made clear in mid-1925, when Fortune magazine estimated Joe Kennedy’s wealth at $2 million, equal to roughly $20 million today. Yet Kennedy had left his most recent job as a stock broker at the firm of Hayden, Stone, and Company in 1922. While he undoubtedly made hundreds of thousands of dollars via stock market investments, only his role as the country’s preeminent whiskey baron could account for such sudden and fabulous wealth.
Through it all, Kennedy maintained his upperworld reputation as a stock tycoon and rising star in the world of high finance and public service—a term Kennedy virtually invented to disassociate himself and his family from the more small-minded, unsavory aspects of Boston-style politics as usual. Publicly, Kennedy’s reputation remained unbesmirched; his meetings with people like Madden, Costello, and Capone were handled in the most discreet manner possible, taking place in hotel rooms or some other highly guarded setting. Although he was known to present expensive bottles of Scotch as gifts or gratuities in his business dealings, Kennedy, like his father, was a teetotaler; he rarely patronized speakeasies or swanky nightclubs. His public life rarely intersected with the mobsters with whom he did business, with one notable exception.
In 1933, shortly after Prohibition had been repealed, Kennedy began an affair with Evelyn Crowell, a Broadway showgirl and the widow of Larry Fay. Fay was the business partner of Owney Madden and fashionable club owner who was gunned down by a disgruntled employee in front of his Casa Blanca nightclub. Before Fay’s corpse was even cold in its grave, Kennedy and Crowell were romantically involved. The affair was well-known enough that, three years later, it appeared as a blind item in Walter Winchell’s widely read New York Daily Mirror gossip column: “A top New Dealer’s mistress is a mobster’s widow.”
After publication of the item, Kennedy arranged to meet with Winchell. The two men became confidants, with Kennedy, legendary for his ability to co-opt journalists, thereafter becoming one of Winchell’s most valuable unnamed sources. In return, there were no more Kennedy references, veiled or otherwise, in any of Winchell’s columns.
The Friends of Joe Kennedy
There is no record of Joe Kennedy’s involvement in whiskey smuggling after 1926. Perhaps, as Prohibition became increasingly homicidal in the latter years of the Roaring Twenties, Kennedy was put off by the untowardly violent nature of the business. Essentially a corporate predator and white-collar criminal, Joe Kennedy was not a mobster in the sense that Owney Madden, Frank Costello, and Al Capone were mobsters; he did not kill men with his own hands. Like most legitimate businessmen who traffic on the dark side of American commerce and profit at some level from organized crime, Kennedy’s role was predicated on the assurance that he would be able to sleep nights without the metaphorical sight of blood on his hands. It may have become increasingly difficult for Kennedy to justify his role as primary supplier in a business that yielded a higher weekly body count than some U.S. wars.
In 1927, Joe Kennedy took his fortune and his penchant for underworld alliances and headed to Hollywood. Kennedy’s years as a Hollywood producer spanned the Silent Era and the dawn of the talkies. Although his cinematic output as a producer at RKO Studios and Film Booking Office (FBO) was decidedly unimpressive, Kennedy manipulated the situation to his advantage and made millions.
In Hollywood, Joe immediately established contact with Johnny Roselli, the underworld’s main representative in the movie business. Years later, at the Church Committee hearings before the U.S. Senate in 1975, the dapper Roselli testified that Joe Kennedy had begun courting him almost as soon as he arrived in town. At the time, Roselli was very familiar with the Kennedy name. Born in Italy and raised in East Boston, the same area where Kennedy’s Irish immigrant grandfather had first settled, Roselli was still living in Boston in 1918 when young Joe Kennedy showered the city’s Italian neighborhoods with money, looking for sluggers to serve as campaign operatives on behalf of his father-in-law, Honey Fitz.
As a youngster, Roselli was a lean and scrappy thug. By the age of seventeen, he’d been arrested twice for narcotics trafficking, once due to a sting operation involving an informant. After spending six months in jail, Roselli was released, and the informant was soon found murdered. When local authorities came looking for Roselli, the young gangster fled to Chicago, where he soon took on an envied role as Al Capone’s personal driver. A handsome man and slick dresser, he became known in the underworld as Mr. Smooth. He was also known to have mastered the art of malocchio, or the evil eye. In later years, he once counseled a friend: “The secret is not to look in [a person’s] eyes. You pick a spot on their forehead and zero in. That way you don’t blink, you don’t move. It intimidates the hell out of them.”
Joe Kennedy was himself known to have this skill, which his family and friends referred to as “Hickey eyes” because he had inherited the trait from his mother, whose maiden name was Hickey.
The Kennedy-Roselli relationship was not exactly a secret. Far removed from the bootlegging centers of the East and Midwest, Joe was more sanguine about mixing with known underworld figures than he had been in the past. The two men occasionally played golf and cards together, and Roselli was an occasional guest at Kennedy’s Beverly Hills mansion. Among other things, the budding movie mogul used Roselli’s influence with various Hollywood trade unions to stave off potentially costly strikes.
Kennedy didn’t need Johnny Roselli to get rich in the movie business. Using techniques he had developed in his years as a Wall Street broker, where he became a master at driving up the price of stocks and then dumping them at enormous profits, Kennedy was an expert at recognizing undervalued corporations. Hollywood had become the fourth largest business in the United States, although few major investors took the industry seriously. “It looks like another telephone industry,” Kennedy told several friends, meaning that it was brand new and ripe for the taking. People in the underworld referred to Hollywood as the new booze.
At the same time that Joe presided as chairman of FBO, he moved around town from company to company, making money wherever he went. He was chairman of RKO Studios for five months, special adviser to First National Pictures for six weeks, special adviser to Radio Corporation of America for two and a half months, and adviser to Paramount Pictures for seventy-four days. He made his biggest killing at Pathé, the venerable newsreel company that had been around since the beginning of motion pictures. Kennedy was brought in as a special adviser and proceeded to plunder the company’s stock. He arranged to pay himself eighty dollars a share, while the average stockholder received a dollar-fifty a share.
Favoring insiders to such a degree was a form of corporate robbery that would be punishable by a prison sentence today. Since Kennedy had acquired his Pathé stock at thirty dollars a share, he more than doubled his investment in little over a year. Stockholders filed suit, but nothing came of it. In Joe’s private papers, Kennedy family biographer Doris Kearns Goodwin found anguished letters from stockholders at Pathé. Wrote Ann Lawler of Boston, who lost her life savings to Kennedy: “This seems hardly Christian-like, fair, or just for a man of your character. I wish you would think of the poor working women who had so much faith in you as to give their money to your Pathé.”
Kennedy’s avarice appeared to know no bounds. He realized that, to truly make a killing in the movie business, he needed to own his own theater chain to distribute his pictures. In late 1929, he sought to purchase the Pantages Theatre chain, whose primary showcase was a resplendent Art Deco movie palace at the corner of Hollywood and Vine. Kennedy made an offer to buy out the entire Pantages chain, the second largest on the West Coast. The company’s ow
ner, Alexander Pantages, an illiterate Greek immigrant, did not want to sell. After several bullying maneuvers against Pantages failed, Kennedy resorted to other means.
On the evening of August 9, a seventeen-year-old woman named Eunice Pringle, wearing a low-cut red dress, went to Pantages’ office inside his theater on South Hill Street in downtown Los Angeles. Several minutes later, the woman ran screaming into the lobby, where she collapsed into the arms of a theater employee, crying, “There he is—the beast. Don’t let him get at me.” She pointed at Alexander Pantages.
A cop arrived on the scene. Pringle, barely coherent, her clothes torn, told the police that Pantages had tried to rape her.
“It’s a lie,” protested Pantages, whose command of the English language was barely adequate. “She raped herself,” he told the cop, meaning that it was some kind of setup. Pantages was arrested and booked on a charge of assault with intent to rape.
The trial was a Hollywood sensation. The main witness, Pringle, was described in the Herald-Examiner as “the sweetest seventeen since Clara Bow.” On the stand, she told a lurid tale of Pantages ripping at her clothes and biting her breast. Pantages, in denying her story, broke into tears and repeated over and over in broken English, “I did not; I did not.” Compared to the seemingly angelic Pringle, Pantages came off as a crude, paranoid foreigner. The jury found him guilty, and he was sentenced to fifty years in prison.
But Pantages appealed the verdict. A team of private investigators unearthed evidence showing that Eunice Pringle was a girl with a past; she was at the very least a professional con artist, if not an outright prostitute. At a second trial, Pantages was acquitted of the attempted rape charge, but the notoriety caused his business to go down the tubes. In November 1931, a few months after Joe Kennedy had made a final offer of $8 million to buy him out, the theater chain owner was forced to cut his losses and sell out to Kennedy’s RKO for less than half that price.
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