The Close Calls of Whitey Bulger

A list of the many times and places in which Bulger could have been caught before now

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For real-life criminal masterminds, escaping police detection on the lam is about more than just blowing on your fingers and faking a limp. It's about the ability to assimilate, the urge to keep moving, and a willingness to take on new physical features and personality quirks as the situation dictates. That's the difference between the recently-apprehended South Boston gangster James "Whitey" Bulger and Kevin Spacey's Keyzer Soze character from The Usual Suspects (he's the guy in the video below). Both ferocious criminals seemed uncatchable, but Bulger was catchable, because he's a man, not a plot device in an over-written movie.

Whitey Bulger eluded capture for 16 years, but was he ever really safe? Judging by the number of near-misses already in the public record before the late-night arrests Wednesday of Bulger and girlfriend Catherine Greig in Santa Monica, the FBI was always just kind of hanging around, waiting to get their man. Last night they did. Here's a list of the various places and times Bulger could have been captured:

Somewhere between New Orleans and Boston (January 1995) The Bulger manhunt could have been avoided had the FBI been keeping closer tabs on him when the racketeering indictments were being handed down. The F.B.I. got a tip on Jan. 5 that Bulger and two associates were planning to flee, but only found one of the three. Bulger was driving back from a vacation in New Orleans when he heard about the warrant that was secretly issued for him. At that point, he peeled off into the void.

Grand Aisle, Louisiana (1995 and 1996)

Whitey and Catherine spent "months at a time" on this island 90 miles south of New Orleans in 1995 and 1996. They said they were Tom and Helen from New York. They took a liking to a young family called the Gautreauxs and "lavished the family with gifts: a stove, a refrigerator, a freezer, toys, clothing, books. Soon the children were calling them 'Uncle Tom'' and 'Aunt Helen.,'" wrote Shelley Murphy in a 1998 Boston Globe story. Penny Gautreaux, meanwhile, defended Bulger on the stand and stonewalled the FBI when agents inquired if he'd placed any subsequent calls to Louisiana.

Boston (October 1995)

With the FBI "chasing tips that Bulger was as far away as Ireland or as close as Cape Cod," Murphy writes that Bulger made his return to South Boston. At a payphone inside Conley Terminal, he called Quantico, Va. and asked to speak with John A. Morris, who once supervised the FBI's organized crime squad in Boston and handled Bulger as an informant. He swore at him, accused him of trying to smear his brother, and hung-up. A weeklong manhunt in South Boston followed.

Long Island  (July 1996)

According to Murphy, authorities on Long Island in early July missed running into Bulger, although they "found the Grand Marquis he had bought there 18 months earlier," and discovered that [i]n the 18 months since he had bought the car, Bulger had driven 65,000 miles. Receipts found inside the Marquis led investigators to Louisiana for the first time. But again, Bulger was gone."

London (September 2002)

Special Agent Richard Teahan of the FBI's Bulger taskforce says that before last night, this was "the last known witness sighting of Bulger." It was also the closest he thinks agents got to apprehending him. "I think we were close then," Teahan said. Bulger was reportedly alone and walking along Piccadilly Square.

Orange County (July 2005)

Well, this one probably wasn't a "close call" so much as a goose chase. Was Bulger the "Elderly Bandit" who ripped off three Orange County banks in 2005? The FBI thought it was possible and sent a team of investigators to look into the matter. You can sense the palpable excitement investigators felt about arresting Bulger in this statement from Laura Eimiller, a spokeswoman for the FBI's Los Angeles office who was asked whether anyone really thinks Bulger and the Elderly Bandit are one in the same. "Absolutely, there's speculation," she said. "But although we can't say it's absolutely not him, we really don't think it is."

Sicily (September 2007)

Another speculative listing. While on vacation in Italy, a DEA agent took out his video camera and started a man the New York Daily News describes as "a vigorous but tense and guarded-looking older man in a cap and sunglasses who resembles Bulger." It really does, but the FBI's facial recognition software read it as inconclusive. Perhaps this will get resolved as Bulger makes his way through the legal system.

This article is from the archive of our partner The Wire.