The Long and Frustrating Hunt for One of America's Most Wanted (Psst: He's Not a Terrorist)

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Illustration by Asaf Hanuka for TIME

Update Appended: June 23, 2011

After 16 years on the run, alleged Boston mob boss James "Whitey" Bulger, 81, was arrested in Santa Monica on June 22. In their hunt for the fugitive with a $2 million reward on his head, the FBI found their search extending beyond the U.S. to Canada, Asia and Europe, where for a time they were convinced he was hiding. But in the end, Bulger was found closer to home, after a 30-second public-service ad focusing on his girlfriend Catherine Greig led to a tip that brought the police to his door.

James Bulger's story reads like the plot of a thousand mobster films. An Irish-American boy grows up in the poor neighborhood of South Boston — Southie — turns to a life of crime and ends up leader of the Irish Mob. Smart, charismatic and generous to those he liked, Bulger — whose blond hair earned him the nickname Whitey — was both feared and revered. At the height of his power in the 1980s, he was allegedly taking a share of almost every drug deal and racketeering operation in Boston.

But since 1995, Bulger, now 81, has been on the run. He fled the city, and probably the U.S., after receiving a tip from the FBI agent he had worked with as an informant that an indictment for federal racketeering was on its way. In the years that Bulger — who is also accused of 19 counts of murder, extortion and drug dealing — has been a fugitive, several of his Mob associates have been arrested and, in some cases, served time. The FBI handler who helped him escape, John Connolly, is currently in prison for his role in the 1982 killing of a businessman who was about to testify against members of Bulger's gang.

There are more than 60,000 fugitives worldwide at any given time, most of whom manage to disappear across international borders, according to Interpol, the global police body tasked with facilitating cooperation among its 188 member countries. And only a small fraction of those fugitives are high-profile crime figures like Bulger. It may have been a stretch when, speaking to the U.S. magazine the Atlantic on May 2, the Pakistani ambassador to the U.S. excused his government's inability to track down Osama bin Laden by pointing to the FBI's failure to find Whitey. But the long, fruitless hunt for Bulger is a perfect example of just how hard it is to track a criminal who has fled to another country.

In 2000 the FBI's Boston branch created a unit with the single purpose of finding the runaway Mob boss. Since then, a team has been following leads across the U.S. and to South America and Asia. Currently the task force thinks he could be in Europe. But even there, where criminals are up against some of the world's best-organized police forces, the search is painfully slow. International crime fighting is painstaking work, and even democracies that cooperate with one another on a whole range of policy matters are reluctant to give up their national prerogatives when it comes to law enforcement.

If Bulger went home to Southie today, he'd find the place much as he left it. The streets are still lined with dollar shops, liquor stores and squat, run-down wooden homes. But Bulger isn't going home. In January 1995 the FBI was readying racketeering charges against him. When former FBI agent Connolly, who had become close to the mobster, heard about the indictment, he warned his old friend. Bulger and his girlfriend Catherine Greig drove out of Southie for good. Almost everything the FBI knows about their movements since has come from interviews with people who knew Bulger, along with clues picked up from searches of his Boston properties. The file on Bulger runs to more than 13,000 separate documents. By talking with FBI task-force members (many of whom asked to remain anonymous for the safety of their families) about what's in that file, it's possible to build a picture that could give clues as to the kind of life Bulger's living.

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The FBI gave TIME's Jumana Farouky a CD with the last known recording of James Bulger's voice. Listen to it here.

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It's not an easy case. In 2001, Bulger's younger brother William — the former president of the Massachusetts state senate for a record 18 years — testified before a federal grand jury in Boston that he had spoken only once to Whitey after he fled, soon after the escape. Six years later, federal prosecutors decided not to press charges in a criminal investigation into whether William had obstructed efforts to find his brother. "It's really difficult to get people to talk to us, because of political patronage and a community over in South Boston that owes loyalty to the Bulger family," says Richard Teahan, coordinator of the Bulger task force.

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