Long Before James ‘Whitey’ Bulger, There Was Joe Kennedy

Johnny Depp arrives for screening of the movie 'Black Mass' presented out of competition at the 72nd Venice International Film Festival on September 4, 2015 at Venice Lido. AFP PHOTO / TIZIANA FABI (Photo credit should read
Tiziana Fabi/AFP/Getty Images

BOSTON – It’s the stuff of Hollywood blockbusters – an ambitious Irish family parlays fabulous wealth generated in the rackets into a spectacular political rise. But in the end, like Icarus, they crash and burn as their sordid, never-severed underworld ties finally drag the arrogant sons down in disgrace and scandal. The Bulgers? Yes, of course.

But long before the ascent of the Bulgers of South Boston came the much greater success of the Kennedys of East Boston. In the earlier rags-to-riches-to-rags story, Joe Kennedy starred in the psychopath-as-patriarch role that Johnny Depp fills as James “Whitey” Bulger in the new Warner Brothers movie “Black Mass,” which opens in U.S. theaters Friday.

Like Whitey, Joe Kennedy was a gangster, make no mistake about it. Mobsters Frank Costello and Meyer Lansky confirmed it late in their lives. That inconvenient fact is the Kennedys’ original sin, and they are still trying to expunge it from the historical record, along with his rabid anti-Semitism, which may have stemmed from his bootlegging wars with Jewish gangsters during Prohibition.

In 1922, it was Joe Kennedy who supplied the booze for the tenth reunion of his Harvard class. One of his classmates wrote, “It came ashore at Plymouth Rock, like the Pilgrims.”

As Prohibition wound down, he journeyed to the UK with Jimmy Roosevelt, crooked son of the new President, and wrapped up most of the lucrative Scotch and gin importing franchises. Joe made millions until 1946 – when he sold Somerset Importers to a consortium headed by New Jersey’s “Public Enemy No. One,” Abner “Longie” Zwillman of Newark.

The fact that Longie was Jewish didn’t seem to bother Joe Kennedy, maybe because Zwillman and his partners were willing to pay $8 million for Somerset.

Joe Kennedy had “hundreds” of women, as even the author of his latest hagiography concedes. Like Longie Zwillman, Joe had an eye for Hollywood sex symbols. Joe’s leading lady was Gloria Swanson, Longie’s was Jean Harlow.

Like Whitey, Joe Kennedy also liked to grab women on the rebound, especially after they’d lost their mates in gangland hits. He had a brief affair with the widow of the late Broadway racketeer Larry Fay. Whitey took up with his last girlfriend, Catherine Greig, after murdering her two brothers-in-law, Donald and Paul McGonagle. She explained to her hairdresser, “I like the bad boys.”

Other than his Nazi cheerleading during his term as U.S. ambassador to the Court of St. James, few of Joe’s scandals were ever reported in the newspapers of the day. The Boston Globe whitewashed Joe Kennedy’s monstrous life just as assiduously as it would later cover up Whitey Bulger’s crimes – “he kept the drugs out of Southie,” the Globe’s top columnist proclaimed, as Bulger flooded the streets of his hometown with cocaine.

Actually, the Bulgers weren’t just following in the footsteps of the Kennedys. The connection between organized crime and politics has long haunted Boston, as it has so many American cities. In the 1930s the leading Southie gangster was an ex-cop named Dan Carroll; his brother Ed was the state senator in the same district Billy Bulger would later represent for 26 years.

The Congressman from South Boston was John McCormack, who rose to become U.S. House speaker. As the state senator before Ed Carroll, McCormack also worked as a lawyer for the Gustin Gang, another early Southie mob. And in 1968, as U.S. House Speaker, he would write his friend FBI director J. Edgar Hoover asking him to hire one of his constituents, John “Zip” Connolly.

Once he became an FBI agent, Connolly began accepting hundreds of thousands of dollars in bribes from Whitey and his gang. Connolly was so close to Whitey’s politician brother, Senate President Billy Bulger, that Billy tried to install the crooked cop as Boston police commissioner.

Connolly was flamboyantly, openly corrupt, even dressing like a New York Mafioso. He was so flush with cocaine cash that he let his paychecks pile up uncashed in his desk for months at a time. The honest agents in the Boston FBI office took to calling him “Agent Cannoli.”

Agent Cannoli is now serving a 40-year state sentence in Florida for a gangland hit in Miami. He is imprisoned in Chipley, 250 miles north of where his paymaster, Whitey, is incarcerated at a federal penitentiary in Sumterville.

In Black Mass, Connolly is portrayed by Joel Edgerton, an Australian actor. The role of Billy Bulger is filled by Benedict Cumberbatch, an English actor. Ironic, considering the Bulgers’ withering contempt for Brits – at his St. Patrick’s Day roasts, Billy Bulger used to tell his Yankee Republican guests, “Thanks for letting us use your country.”

In the 1960 presidential campaign, it was Joe Kennedy who reached out to the underworld to help his son win the presidency. Although he knew many of the hoodlums personally, he preferred to use Frank Sinatra as his emissary. Sinatra’s valet George Jacobs later recalled Joe’s first visit to Sinatra in Palm Springs in 1958, describing Kennedy as “another pillar of the underworld.”

“The man may have had a Harvard degree,” Jacobs wrote in Mr. S, “but was a disgrace to it, cruder and meaner and, alas, proving crime does pay, more successful than any of the street mobsters Mr. S had ever hosted.”

Whitey Bulger does not have a Harvard degree. But his FBI agent, John Connolly, did get a graduate degree from Harvard in 1982 – while he was simultaneously setting up the waterfront double hit that is one of climactic scenes in the movie. A year later Billy would try to force a new mayor to appoint the hit man as police commissioner.

From Harvard to City Hall to the meanest gangland dives – it has been ever thus in Boston. As Edwin O’Connor wrote in “All in the Family, “Underneath everything in our politics there seemed to be a depthless cushion of street-corner cronyism, a special kind of tainted, small-time fellowship which sent out a complex of vines and shoots so interconnected that even the sleaziest poolroom bookie managed in some way, however obscure, to be in touch with the mayor’s office or the governor’s chair.”

Or, as William Faulkner once said, the past is never dead. It’s not even past. Especially in Boston.

In 1960, the older mobsters across the nation remembered Kennedy’s Prohibition double crosses, hijacking his own truckloads of bootleg liquor in order to sell them a second time. When the question of merging with the JFK campaign was put to the elders of the Chicago Outfit, elderly mobster Murray “the Camel” Humphreys denounced Kennedy as a “four flusher,” according to Seymour Hersh in “The Dark Side of Camelot.”

But Humphrey was outvoted by his Italian associates, and the die was cast. LBJ stole Texas, and Sam “Momo” Giancana pilfered Illinois’ electoral votes with the help of Chicago Mayor Richard M. Daley. But Humphrey’s warnings proved prescient – despite Joe Kennedy’s promises to lay off, his sons reneged, and went after the Mafia once they were installed as president and attorney general, respectively.

Santo Trafficante Jr., the Mafia boss of Tampa, was particularly irate. In 1957, he had entertained Sens. Jack Kennedy and George Smathers at one of his pre-Revolution resorts in Havana, supplying three hookers to JFK, according to T.J. English in Havana Nocturne.

Carlos Marcello, the Mafia chieftain of New Orleans, had been personally recruited to the JFK campaign by both Joe and Bobby Kennedy, but stuck with Richard Nixon. In 1961, AG Bobby ordered Marcello summarily deported to Guatemala. When he returned, Marcello began to plot with Trafficante to “remove the stone from my shoe,” as an FBI wiretap recorded him saying in his Sicilian dialect. Trafficante told a Cuban associate of JFK: “He is going to be hit.”

Like the Kennedys, Whitey Bulger likewise betrayed his Italian cohorts. He became a rat for the FBI, in addition to bribing at least six G-men in Boston. But in both cases, some accommodations could have been worked out – if only the street-wise patriarch had been around.

In December 1961, Joe Kennedy suffered a debilitating stroke in Palm Beach. He was left unable to speak. He could no longer mediate between his fellow gangsters and his spoiled rich-kid sons. Frank Sinatra, the old man’s go-between, was distraught.

“Only the master strategist Old Joe,” Sinatra’s valet wrote, “could tell Frank how to sort this out, and by now, Old Joe wasn’t talking. What a can of worms!”

By 1968 both older Kennedy brothers had been assassinated, leaving as the family’s only male survivor Edward Moore Kennedy, of whom John McCormack’s nephew said in their famous 1962 Senate debate, “If your name were Edward Moore, your candidacy would be a joke.”

As for Whitey, as long as he was at large, his brother never lost an election. Maybe because Whitey threatened to murder any political rival, businessman, girlfriend, reporter or anybody else who crossed any member of the Bulger family – and sometimes did.

In late 1994, Whitey went on the lam ahead of a federal indictment. Billy never risked another election. Instead he tried to pass his Senate seat on to his son, Billy Bulger Jr. With Whitey no longer prowling the streets of Southie, his nephew was crushed in the Democratic primary in 1996.

Joe Kennedy died in 1969 at age 81. Whitey turned 86 earlier this month and will die in prison. The Kennedys are down to a single seat in Congress, held by one Joseph P. Kennedy III – a straight white male, not exactly a dream Democrat candidate these days, in Massachusetts or anywhere else.

This is shaping up as a big weekend at the box office for movies about corrupt Irish-American families built on blood money. Still, as time passes, it seems hard to believe that such terrible corruption could have ever occurred in America.

But then, as one of Whitey’s rat grave-diggers pointed out at trial, “We weren’t in America, we were in Boston.”

Howie Carr’s novel about the nexus of organized crime and politics in Boston, Killers, has just been published by Macmillan. He has also written two New York Times bestsellers, The Brothers Bulger and Hitman.


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