The Old Man Next Door

The last days of America’s most wanted mobster, James “Whitey” Bulger

About half a dozen agents in the bureau’s Boston office landed on Bulger’s payroll, including its top administrator, John Morris, and his subordinate, Connolly, a gregarious wheeler-dealer who had grown up in the same housing project as the Bulger family. Initially the data that Connolly and other agents provided FBI informant BS 1544 TE, as Bulger was designated, allowed him to identify FBI and police informers who needed to be eliminated. But then the intel was used to warn Bulger of pending arrests and other actions against him being planned by non-FBI law enforcement agencies. Rumors of Bulger’s special arrangement with the FBI tainted the bureau’s Boston office in the eyes of other police agencies for years.

The demise of Bulger’s criminal Camelot came, fittingly, after he was snitched out by a bookie in 1992. As a result, by 1993 a task force of state police and federal Drug Enforcement Agency cops was organized to catch Bulger—a coalition that deliberately cut the FBI out of its operation and kept it secret from the bureau as long as possible. Connolly retired in 1990, but his FBI radar was still very much online. In the final days of 1994, he was able to warn Bulger and Flemmi one last time of plans to apprehend them. Flemmi, believing he was arrestproof, remained in Boston and was taken into custody; his eventual conviction on murder charges led to a life sentence.

Bulger and his longtime girlfriend, Teresa Stanley, however, fled to Europe, Florida, and New Orleans, relying on cash that he had stashed in far-flung bank deposit boxes. But Stanley grew homesick for Southie, so Bulger had to return to Boston and trade her in for Catherine Greig. When the pair tried to create new lives for themselves in Grand Isle, Louisiana, Stanley gave up Bulger’s alias to Boston FBI agents—who dutifully informed Bulger’s remaining lieutenants so they could let him know. The warning, along with the Boston FBI’s purposely bungled search for Bulger and Greig, enabled the couple to stay well out of reach of their captors for years.

In 1998, however, a cornered, retired John Morris testified before a federal judge about his bureau’s corruption and Whitey Bulger. Morris’s appearance earned him immunity from prosecution, but the FBI finally arrested Connolly for obstruction of justice and racketeering. He was convicted and sentenced to ten years in prison—after which he began serving a 40-year term on a 2008 conviction for second-degree murder for his role in setting up two victims to be killed by Bulger’s men.


There had been no escape from the media for Bulger’s old neighbors in the days that followed his arrest. Reporters tried to sneak into Apartment 303, while across the street at the Embassy, whose rooms had no air-conditioning, residents who left their windows open during the summer night were kept up by the activities of reporters and news van crews. Visiting Bostonians would ask locals to take their pictures as they stood next to the Princess Eugenia’s sign. Then there were the tour buses. “Whitey Bulger lived in this apartment building!” neighbors heard guides announce over loudspeakers.

But the excitement was nothing compared to the media scrum drawn to Boston for Bulger’s two-month trial. While legal experts speculated whether he’d testify, his lawyers began with an extraordinary move, seeking to claim that a deceased federal prosecutor had granted Bulger and Flemmi blanket immunity for their information to the FBI—essentially a license to commit any crime they wanted, including murder. Absurd as the defense might seem, it would have potentially opened the gates for testimony about FBI corruption and the complicity of individuals in other law enforcement agencies. Bulger’s judge wouldn’t permit the argument. The defense attorneys were left to claim that he merely pretended to give away secrets and that the information he received from the FBI was not part of a reciprocal exchange; rather it was a product purchased by Bulger with hard-earned blood money. The spin was intended to make the gangster somehow look less like a rat and more like a shrewd businessman.

Steve Davis, whose sister had disappeared 32 years before, was a constant—and sometimes volatile—presence in and out of court, at one point loudly correcting Stephen Flemmi’s testimony from the gallery. Burly and tattooed, Davis was a man obsessed with avenging Debra’s murder and a reminder of the human wreckage Bulger stood accused of leaving in his wake. Davis speaks in a Southie accent that is vanishing among residents of that gentrifying neighborhood. “My wife says, ‘I can smell fall in the air. What are we going to do for Labor Day?’ It’s only a few weeks away, but I was so tied up with this trial the whole summer, I lost track of time,” he said days after the proceedings ended in August.

During Flemmi’s six-day appearance, the two former partners occasionally spat epithets at one another, each accusing the other man of being a rat. In the witness chair Flemmi denied being friends with Bulger, despite their sometimes vacationing together. He described his relationship with Bulger as “strictly criminal” and said, “Bulger kind of resented the fact that I didn’t spend enough time with him…. He would contact me, and I wouldn’t respond.”


This feature originally appeared in the October 2013 issue of Los Angeles magazine