The Winter Hill Gang: Racketeering, race-fixing, loan-sharking, extortion, a networked army of drug dealers and bookies all across Boston, all of them loyal through fear. An underground network so comprehensive that it would take decades to bring down. And for decades, law enforcement officials have been digging.
The digging continues, and it is beginning to yield answers. Digging in the ground beneath some MBTA tracks in Quincy, for instance, yielded Winter Hill "rival" Tommy King, not far from a one-time girlfriend of Stephen "The Rifleman" Flemmi, who apparently got too close. Kenneth Conrad, a Boston bartender who is alleged to have seen something he shouldn't have, was unearthed in a suburban backyard in Canada. Investigators spent days digging outside the Hopkinton Sportsmen's Club for Walter and Edward "Wimpy" Bennett, and though they were unable to find them down there, they're taking "Cadillac Frank" Salemme for his word, assuming that they're under there "somewhere."
Kevin O'Neil and Kevin Weeks, high-ranking Winter Hill'ers who ran an appliance store as a front, went down in November '99 on racketeering charges. It seems they'd been demanding what they referred to as "rent" from bookies, on at least one occasion warning that a stay in payments warranted "break(ing) his head open." Stephen "The Rifleman" Flemmi has also gone down, opting for the risky plea strategy of going public with just how much he and bossman James "Whitey" Bulger assisted the FBI with information, even as they were gunning people downin the '60s and '70s: so that if he does manage to finnagle a shorter sentence, the Sicilian mob, the Italians, and La Cosa Nostra will be hunting him down for the rest of his short, free life.
One particularly helpful informant trading information for a plea-bargain is ex-hitman John Martorano. He was so pissed to hear that uber-boss James "Whitey" Bulger and The Rifleman had been talking to the Feds all that time, that he's talking up a storm in exchange for a 12-year murder sentence. One can only shake one's head when the sentence of a career murderer is commuted to 12 years in exchange for some information--one year for each murder he admits to committing: ten in Massachusetts, one in Florida, one in Oklahoma. Pretty generous deal.
Meanwhile, crimelord Whitey Bulger is on the run, and he's running far and wide: sightings in Ireland, Italy, California, Florida, even right back there in Boston, where he's something of a celebrity ghost-story figure. What with being on the FBI's most wanted list, a distinction that bears with it a $1,000,000 turn-his-ass-in-dead-or-alive payout clause, chances are he'll keep running. Now that Cadillac Frank and The Rifleman have spilled the beans on Whitey's long-time FBI informing, the Sicilians and the Italians have added heat to a hostile world of bounty hunters and Feds, the latter of whom are exceptionally motivated in the chase, as they're taking flack for letting him slip right through their fingers.
See, right about the time when Whitey Bulger offed Wimpy, he had a deal with the FBI: he'd keep talking, giving them the goods on the Sicilians and the Italians (who were, incidentally, encroaching upon his "market share") in exchange for the right to fix the occasional race and beat the hell out of the occasional debtor. But the deal was: no killing. Somehow, the FBI wasn't keeping tight enough tabs on the wily Irishman, who then proceeded with business as usual, in the machine gun, trunk-of-an-abandoned-rental-car-in-an-airport-parking-lot sense. How could this happen? An oversight?
Former Boston FBI agent John Connolly got pretty close to Whitey over the course of so many interrogation secessions, and Agent Connolly needed a new refrigerator. He went to an appliance store, he picked one out, and the proprietor, Kevin Weeks, delivered it to his home personally. Paying for it never came up. It must have been hard for Agent Connolly--he walks into the liquor store, picks up a couple things, and when the proprietor insists you not pay, what do you do? Next thing you know, Connolly's not paying for anything: he is king of the town. Soon, he's accepting cash as well. Meanwhile, he becomes one of the most respected FBI agents in Boston--"largely because of his role in securing indictments and convictions that decimated the Italian Mafia..." Whitey had the FBI working for him, just like that.
Perhaps most alarming of all about the Connolly situation, as has been dug up in subsequent investigations of his practices, was that Connolly was known to have taken visiting FBI agents to the State House for tours, making a point of introducing them to the State Senate President: William Bulger, brother of known murderer and Winter Hill Gang overlord Whitey Bulger. President of UMass up until August '03, when he stepped down under mounting public and political pressure, William Bulger vehemently denies having had any contact with his brother for years.
Where the Winter Hill Gang begins and ends, that is impossible to say. Even after so much digging, one can never be certain that there isn't so much more underground. Do we consider Connolly a part of the organization? J. Edgar Hoover's FBI of the '60s was more directly guilty of sponsoring far greater crimes than Connolly ever did. Take, for instance, the case of Winter Hill gang member and informer Vincent J. Flemmi. While informing, he mentioned a murder he intended to perpretrate, and noted his accomplice, Joseph "The Animal" Barboza, by name. They killed Edward "Teddy" Deegan and left him to be found in an alley. The FBI then stood idly by as Barboza became the star witness in the successful prosecution of four innocent men, two of whom died in prison before the scandal broke. "The government stole more than 30 years of my life," remarked an outraged Joseph Salvati upon his release. FBI Agent H. Paul Rico, an interrogator at the time of the trial, believes the FBI handled things properly, that the information gleaned from leaving The Animal on the streets was a benefit that outweighed the gross injustice: "Remorse - for what? Would you like tears or something?" He adds that the story might make for "a nice movie."
And all the while, since 1995, Whitey has been running. He is now over 70 years old. People want him dead, people want him for money, people want him for justice, people want him simply because it's their job to hunt him. He's the 458th man to be put on the FBI's Ten Most Wanted list, and 429 have been caught. Still, there may be a lot more digging to do if the FBI is ever going to get its hands on the man. Perhaps they should begin by digging up some gardens in the backyards of Sicilian Mafioso.
October 10, 2003: Agent Rico has been indicted on murder charges. Apparently, he left the FBI to become chief of security for a businessman who had been skimming from Winter Hill interests, and that man was promptly bumped off. Is anyone not involved in the Winter Hill Gang?