Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (11 page)

“He didn’t want to see us get indicted,” Flemmi explained, and the FBI culture provided Connolly with the room he needed to improvise; he could talk the talk of the manual but also make up his own lines along the way.

Five months after Whitey Bulger was opened up as an FBI informant, Connolly succeeded, on February 2, 1976, in having him elevated to top echelon status. The Boston-bred agent now had two “TEs” in hand, Bulger and Flemmi. Flemmi, once “Jack from South Boston,” became known as “Shogun.” Bulger was “Charlie.”

But cracks—small fissures, but cracks nonetheless—began to show. “Connolly fashioned himself as a very important guy,” recalled Robert Fitzpatrick, a seasoned agent who became an assistant special agent in charge (ASAC) of the Boston office in the early 1980s. He always seemed to be moving around the city working people in the media, in politics, and at the office. He became the go-to guy for Red Sox tickets. On occasion Connolly failed to make the mandatory morning sign-in. His manner began to change, and his style became more charged. He began to operate like a salesman—skilled at feigning sincerity but uninterested in the real thing. It was the consummate skill of a great pretender, a skill that became his hallmark.

And he’d apparently outgrown his marriage. John and Marianne Connolly separated in early 1978. He promptly relocated to an apartment in Quincy just a few blocks from the beach road where he’d met with Bulger that moonlit night. The apartment was also practically across the street from the Louisburg Square condo complex where Bulger bunked with Catherine Greig, the younger of his two girlfriends. But for Connolly, Quincy was part of a journey, not a destination. He began thinking about moving back into Southie.

Fitzpatrick was one FBI manager who began having reservations. He and Bulger and Connolly had a secret meeting, a rendezvous that was part of a required, periodic supervisory check of an FBI handler and informant.

“I let him bullshit,” recalled Fitzpatrick, about how Bulger immediately took control of the session. Bulger talked about his weight lifting, the good shape he kept himself in.

“He did a lot of talking. He did a lot of bragging—what I would consider bragging—about how strong he was, what he was doing in prison. He told me about his background. We talked about Southie. And generally speaking, it was my impression that he was trying to impress me.”

After the meeting, Connolly told his FBI boss, “Isn’t he a great fuckin’ guy?” Fitzpatrick never forgot agent Connolly’s line. Bulger, the reputed killer, loan shark, and drug trafficker—a great fuckin’ guy? Fitzpatrick blanched.

IN AN office where some agents had their doubts, managers took comfort in the December 1977 promotion of another agent to oversee Connolly. The new supervisor of the Organized Crime Squad, veteran agent John Morris, was viewed as a good match for the savvy street agent, a straight-arrow supervisor who could serve as counterpoint.

The two paired off like an odd couple. Connolly was gregarious, tall, and dashing. Morris, a man of midwestern origins, was quiet and plain-looking. Connolly was a free man moving about the town. Morris was married, with a family. He lived in the suburbs, often commuted to work with Dennis Condon, and was considered a smart, capable manager whose paperwork was thorough and of high quality.

But over time Morris would himself turn out to be the polar opposite of a role model. The FBI brass had made a horrible mistake. The intense, thin-lipped Morris was no match for all that was brewing inside the Boston office of the FBI. The deal between Connolly and Bulger and Flemmi was going to turn out to be bigger than Morris could handle—bigger than any subsequent supervisor, or even the FBI itself, could handle.

The third race
at the Suffolk Downs racetrack was set to go according to script. The Winter Hill gangsters were standing by in Somerville in eager anticipation. Led by Howie Winter, and including associates Whitey Bulger and Stevie Flemmi, they had placed thousands of dollars in bets at both the track in East Boston and with bookmakers.

Time to sit back and smell the roses.

But something was wrong. One jockey, who’d been paid $800 to do his part, had decided to improvise. Instead of holding his horse out of the running, he’d raced hard to the end. Bets had been made, and now money had been lost. Howie Winter was not happy.

In the back room of a restaurant in Somerville, the jockey dutifully showed up for a postrace secret meeting. Winter was there waiting, along with one of his henchmen and the fixer himself, Anthony “Fat Tony” Ciulla. Howie Winter had gone into business with Ciulla in order to make big money off horse races up and down the East Coast. Known as the “master fixer,” Fat Tony was a hulking beer keg of a man: six-feet-four and 230 pounds.

The menacing Winter got right to the point.

“You realize you took my money and allowed your horse to run?”

The jockey was nervous. He tried responding with a light touch, but his remark came off as flip. Before he could finish, Winter’s sidekick, Billy Barnoski, whipped out a blackjack and whacked the jockey on the head. For good measure, Winter stepped up and slapped the jockey’s face.

The jockey decided to adjust his attitude. Profusely apologizing, he offered to hold back horses in upcoming races for nothing. Winter wasn’t sure. There had been talk about killing the jockey and dumping his body in the back stretch of Suffolk Downs. Nothing like a cold corpse to send a message.

But Winter decided the beating itself would suffice. The mangled race result in mid-October 1975 probably signified nothing more than a rare bad day. Federal prosecutors estimated that the gang’s race-fixing enterprise with Ciulla had amassed more than $8 million in profits while operating in eight states. It could afford to lose one race.

IT WOULD always be Connolly’s position that the extent of the Boston FBI’s knowledge of Bulger and Flemmi’s criminal activities was narrow—restricted to the gambling and loan-sharking the two had going in order to maintain their underworld credibility. But the truth was that Bulger and Flemmi had all kinds of rackets going, including the racetrack plot.

The scheme was straightforward. Using bribes and intimidation, Ciulla made sure that certain horses, usually the favorites, lost. Depending on the jockey and the horse, the bribes ran from eight hundred to several thousand dollars. Meanwhile, Winter’s associates were putting down bets on the long shots, either to win, place, or show or in various high-paying combinations; in a trifecta, for instance, a winning bettor picked, in sequence, the first three winners. The gangsters spread their bets around, at the track, with bookies in the Boston area and with bookies out of Las Vegas. In some races handicapping the outcome of the race was a cinch. For instance, the field at Pocono Downs in New Jersey was often small. Ciulla bribed three of the five jockeys, and then watched the money roll in.

For his part, Ciulla really had no other choice but to hook up with Winter’s gang. The son of a fish merchant, Ciulla grew up in the Boston area tagging along with his father to the track. He began fixing races in his twenties at tracks in Massachusetts and Rhode Island, sometimes bribing jockeys, sometimes drugging the horses. By late 1973 the thirty-year-old hustler had made the mistake of hoodwinking bookmakers controlled by Howie Winter. The crime boss discovered he was being “victimized” by young Ciulla. Winter decided to pay Fat Tony a visit.

Ciulla recalled meeting Winter at Chandler’s Restaurant, a restaurant in the South End of Boston that Winter controlled. “He told me he knew I had bet with his bookmaker, Mario, on a fixed race.” The amount was $6,000. “He told me I was responsible for beating him out of X amount of dollars and that I would have to make this money good or otherwise I would be in trouble.”

But by the time they were finished talking the beef had evolved into a new business opportunity. Soon afterward the two met again in Somerville. They talked some more. Then, near the end of 1973, they convened at Winter’s Marshall Motors. This time Winter had his inner circle present, including Bulger. Terms were negotiated; techniques were discussed. For each party there was a strong upside. Ciulla had the racing expertise. He knew the tracks, the jockeys, and the horses. Winter had the access to bookies. He and his associates also had the deep pockets to finance the substantial betting action they all had in mind. Just as important, Winter Hill brought along its muscle to ensure that the bookmakers they exploited would not think about retaliation if and when they realized they’d been cheated.

Starting in July 1974, Ciulla and Winter’s gang began fixing horse races along the East Coast—in East Boston (Suffolk Downs), in Salem, New Hampshire (Rockingham), Lincoln, Rhode Island (Lincoln Downs), Plains Township, Pennsylvania (Pocono), Hamilton Township, New Jersey (Atlantic City), Cherry Hill, New Jersey (Garden State), and at other racetracks as well.

Then things went wrong. A jockey in New Jersey began cooperating with state police. Ciulla was busted, convicted at trial, and sentenced to serve four to six years in New Jersey state prison. But Fat Tony did not cotton to prison life. By late 1976 he’d begun talking too. The New Jersey State Police brought in the FBI, and suddenly, in early 1977, Ciulla was plucked out of prison and deposited into the federal witness protection program. In return for leniency, Ciulla was going to reinvent himself as a star government witness, and in the early days of 1977 he began talking to agents about his venture with Howie Winter’s gang, about the regular meetings at Marshall Motors with Winter’s crew, about Bulger, and about Flemmi, who in 1974 had returned to Boston from Montreal.

BACK in Boston during the early part of 1977, word about Ciulla’s career change was not widespread. Though FBI agents in Boston were assigned to the case, Connolly was not one of them. John Morris had yet to take over as supervisor of the Boston office’s Organized Crime Squad. None of the controls were in place that in the future would help snuff out inquiries into the prized informants. The race-fix probe had gotten under way out of state and only then looped back into Boston. It was all happening beyond Connolly’s control. No chance for Melotone-redux.

The FBI case agent was Tom Daly, who worked out of Lowell, Massachusetts. Daly later grew close to Connolly but for now was discreetly developing Ciulla as a major trial witness to take down Howie Winter and his gang. Things got even more complicated not long after John Morris stepped into the picture as Connolly’s new supervisor. The FBI could not be running informants who were simultaneously targets of a major FBI case. Thus, Morris ordered the top echelon informant shut down. Bulger, wrote Morris in a memo, was being “placed in a closed status at the present time as subject could possibly become involved in legal difficulties in the near future.” Connolly himself had no choice but to sign off on the report of January 27, 1978, that was placed in Bulger’s administrative file and sent to FBI headquarters in Washington, D.C. The bureau’s guidelines and regulations for handling informants required no less.