How was it that in civilized Massachusetts, urbane Boston, the “Athens of America”, no one was ever seriously bothered by fact that for almost thirty years, Billy Bulger, President of the State Senate and most powerful politician in Massachusetts, and James “Whitey” Bulger, the man who controlled the cocaine distribution in northern New England, were brothers?
When I was a kid, the fact was acknowledged, and attributed to the peculiar culture of South Boston “where every family produces a priest, a politician, a policeman… and a gangster.” Billy was widely seen as a decent man devoted to his city, not responsible for his brother’s sins. Whitey, it was claimed, was really not as bad as all that. Sure he had robbed banks as a kid and did his time; sure there were rumors, maybe he was hijacking trucks or shaking down bookies… but cocaine? Never! Murder? Of course not!
Plenty of reporters and columnists accepted and repeated the narrative of the lovable Leprechaun Billy and his shadowy rascal of a brother. Others, who investigated too deeply into a grisly murder or shady state contract were told to stop unless they wanted their wives and children murdered.
Howie Carr, newspaperman turned radio-shock jock, while not exactly a hero, was one of the reporters who never bought the narrative about either of the brothers Bulger. Carr was on the receiving end of Whitey’s threats and he made his career lampooning corruption in the State Legislature, so he is well positioned to write a book about it. Others have written the story of Whitey’s relationship with the spectacularly corrupt FBI agents who helped him, but in The Brothers Bulger Carr chooses to focus on the parallel careers of Whitey and Billy, the latter enabling the former.
Like most American cities, Boston politics revolves around a Democratic Party political machine that is basically a system of patronage. The politicians ensure their popularity by handing out favors, mostly in the form of fake jobs or disability checks, to as many people in their home neighborhood as they can. Public transportation, the police, the teachers, the fire department, any possible public service is brought into the system. The employed in turn makes sure that the votes and union dues go back to the same politicians come election time.
Of course, such a system is hopelessly inefficient and corrupt, and it eventually bankrupts the city. But Billy Bulger was a master of it and it made him a powerful man. The effects of his patronage were seen throughout the city: hopelessly overrun building costs, public works bleeding funds, and massive holes blown in the state budget. But connected people in Southie could get a job and not have to work hard at it. In fact, when in 1993 the DEA arrested Whitey Bulger’s entire network of coke dealers, every single one of them either had a government job or was receiving a disability check.
Billy built his career on patronage and ruthlessly ruining the careers of his critics. Whitey built his career on patronage, and killing anyone who stood in his way. Once or twice Billy shook down construction companies the way Whitey habitually shook down bookies. Billy took control of public works, hid the books from the press, and ran them into debt to enrich his friends, the way Whitey took over liquor stores and bars and bled them until they folded.
While Billy learnt the laws of patronage in the halls of power, Whitey learned them as teenager working nights as a prostitute in Boston’s underground gay bars: there he met H. Paul Rico, FBI agent. It was probably Rico who later got Whitey out of his first jail stint, and it was definitely Rico who set him up in Boston’s underworld working as an informant. First Rico, then other agents, let Whitey Bulgar murder his way to the top of organised crime in Boston, in part because they preferred Irish mobsters to La Cosa Nostra, and in part because they knew Whitey’s younger brother was an up-and-coming politician. They knew that by being friends with Whitey, they would get favors from Billy, mostly in the form of high-paying jobs in public utilities companies.
Billy always kept distance from his brother. He always claimed that he was ignorant of any evil deeds committed, and he probably was, but willfully so: he knew the FBI agents who protected Whitey and got them all jobs. FBI Agent Tom Connolly, a South Boston native, had helped manage one of Billy’s early campaigns before Billy got Tom Connolly into the FBI. Tom Connolly later was a close friend of Whitey, feeding him tips and framing others for his murders, becoming one of the most corrupt agents in the Bureau’s history.
Billy lived next door to the mother of Whitey’s closest partner, Stevie “the Rifleman” Flemmi, serial killer and pedophile. Stevie and Whitey hid guns, drugs, cash, and the mutilated bodies of a couple of Stevie’s girlfriends in Mrs. Flemmi’s house, with the knowledge of Agent Connolly, whom Billy later recommended to the Mayor for the role of Police Commissioner. (The mayor, the charming, athletic, alcoholic Ray Flynn, later Ambassador to the Holy See, refused, making him Billy’s enemy.)
The only time Carr shows any sympathy for Billy (“the corrupt midget”, was Carr’s nickname for him on his radio show) was for his role in the busing crisis of the 1970’s. Boston, like so many other cities, had a problem: schools were paid for at the local level, meaning the lower-middle class ethnic neighborhoods like Southie or the North End had more money to spend on schools than a poor black neighborhood like Roxbury. Worse, since the white ethnics were running the political machine, their schools got more of the city-wide funds. Critics claimed this was de facto segregation, and it had to stop.
The solution imposed by politicians and judges at the state level was to bus some of the black kids to the white schools, and some of the white kids to the black schools. The ethnic whites of Boston (and any other city this happened in) put up a ten year legal battle, and in the end resorted to barricades and riots. Billy Bulger was one of the leaders of the failed effort against busing.
It is commonplace to condemn the opposition to busing as simple racism, but it was not. Inner city black communities in the 60s and 70s were extremely dysfunctional: gang violence, drug abuse, broken families, jail time for teenage boys and pregnancy for the teenage girls were not the exception but the norm. The white ethnic neighborhoods like Southie however were relatively healthy. Now the white ethnics were expected to send their own kids to the poorest preforming, most violent schools in the state, and accept among their own kids children whom they had every reason to expect would bring a culture of drugs and violence with them.
Of course, the wealthy liberals who were pushing for the new rules lived just outside the city line; their children, if they attended public school at all, would therefore not be subject to busing. The liberal wing of the Democratic Party was preforming a social experiment on the children of the conservative wing of the Democratic Party, the effects of which they would never suffer themselves.
By opposing busing, Billy Bulger was going against the liberal direction of the party, and while he never lost popularity in Boston, his chances at statewide office were destroyed.
The experiment, by the way, failed: the schools of Roxbury did not improve. The schools of South Boston got worse. Between the cratering schools and ever higher taxes (thanks to inefficiencies of their own patronage machine) middle class whites who could afford it started fleeing for the distant suburbs, leaving their poorer neighbors to fend for themselves. Without the stabilizing presence of middle class families, the neighborhoods deteriorated into a familiar pattern of violence, drugs, and broken homes. (This phenomena was repeated in hundreds of cities; a death spiral that destroyed urban culture in America for at least a generation.)
Ironically, Billy Bulger’s defeat gave Whitey Bulger a new market in which to sell drugs: the poor whites of South Boston.
By the mid-nineties the FBI was finally coming to grips with the corruption in its Boston office and the extent of Whitey’s criminal activity, and the Massachusetts Democrats were getting sick of having Billy boss them around. The Boston Herald and even The Boston Globe, usually more deferential to the Bulgers started reporting on political scandals and, for the first time ever, began mentioning in print what the whole world knew, that Whitey ran the mob in Boston. Whitey went into hiding 1994. Billy retired from the Senate to the Presidency of the University of Massachusetts, whose money he looted for himself and his friends, usually with the help of Governors who owed him favors.
Come the early 200os, the corruption of the FBI in Boston had become the subject of a congressional investigation, and at this point it seems the first politician in thirty years who owed nothing to Bulger came on the scene, newly elected Governor Mitt Romney. Romney insisted Bulger cooperate with the investigation, and refused to pull strings on his behalf. Romney then leaked the finances of UMass to the press, so the whole city could see the six figure salaries being paid to layers upon layers of unqualified bureaucrats hired by Bulger. Finally, Romney announced that instead of appointing Bulger’s recommended sycophants to the University’s board of trustees, he would appoint a retired judge whose career Bulger had destroyed 20 years before, Harvard Law professor Alan Derschowiz, who had represented clients in civil suits against Bulger’s attempted shakedowns, and radio shock-jock Howie Carr.
Billy got the hint and retired, but not before granting himself a six-figure pension.
Whitey Bulger ran from the FBI for the better part of two decades before he was captured in Santa Monica, California in 2011, at the age of 81. He was convicted of racketeering, extortion, narcotics distribution and 19 counts of murder.
Every family in Southie produces a priest, a politician, a policeman… and a gangster. The truth is that for the dock-laboring families of South Boston in the first half of the 20th century, those were the only ways they could imagine to escape poverty. It is not a wonder then that Southie produced so many political hacks and crooked cops, and 9% of its priests were pedophiles.