Just the mere mention of the name “Whitey Bulger” sends chills down any South Boston resident’s spine. The infamous Irish gangster left a torrent of bloodshed and crime in his path as he strolled down the alphabetized streets, out of the grasp of crime enforcement agencies. But after a 16-year hunt, the law has finally clenched its fist and arrested Whitey.

James J. “Whitey” Bulger and his girlfriend Catherine Greig were arrested on Wednesday at their apartment in Santa Monica, Calif., just days after the FBI launched a female-oriented publicity campaign on daytime television to capture the couple. Ads were run on television and billboards featuring pictures of Greig.

“It’s very big deal, its a significant deal,” said Brad Bailey, a noted Boston defense attorney. “Obviously at 81 years old, regardless of whatever sentence could be imposed, it’s clear that he could be spending the rest of his natural life in prison.”

Bulger led a long life of crime not only in Boston, but also throughout the country. He was first arrested at age 14 for theft, and so began his tumble into delinquency. From there he committed various crimes, which landed him in a juvenile detention center for five years. He then joined the Air Force, where he served time in military jail for assault. Bulger returned to Boston and waged a string of bank robberies from Rhode Island to Indiana, which earned him 25 years in federal prison. He only served nine of those years.

After his release in 1965, Bulger joined Boston’s Winter Hill Gang and quickly rose through the ranks. By 1979, Bulger assumed leadership of the gang and became in control of much of Boston’s drug trade and gambling operations. He has been charged with 19 murders.

Bulger instilled fear throughout the whole neighborhood, but also provided a level of security. He would help kids or local businesses as long as they helped him, however if one of the people he helped made one wrong move, he would get revenge, often much worse than the original infraction.

It was this volatility that sparked the fear.

But Bulger threw a wrench into the gang’s operation, as he often liked to do: he was an FBI informant. He told no one of his position, even his right hand men. With this power, he helped take out the Italian Patriarca crime family, decimating the Italian mafia in Boston, and consolidating his empire in their wake.

This relationship with the FBI proved to be very helpful to Whitey. He avoided various murder charges, including one in 1982 when Bulger and Stephen “The Rifleman” Flemmi, gunned down a former Winter Hill member in broad daylight. Whitey’s FBI handler, John Connolly, filed an FBI report saying that a rival gang member was responsible for the killing.

In 1995, as law enforcement finally closed in, Connolly warned Bulger about his pending arrest. Bulger was able to flee and avoid arrest for the following 16 years. He landed on the FBI’s Ten Most Wanted list, second to Osama Bin Laden.

Although Whitey was on the run, he wasn’t all that hidden. The FBI received a slew of tips as to where he was, had multiple sightings, they took recent pictures of him, and knew his favorite hangouts. Nobody is quite sure why it took so long to apprehend the mobster.

“I think that’s anybody’s guess,” Bailey said. “It would appear that for him to be living in Santa Monica he was hiding in plain view. There are all sorts of levels of speculation of why it took so long, but the fact is that now he has been apprehended.”

The FBI has been battling accusations that they were not trying very hard to find Bulger for the past few years. This is partly because of Bulger’s informant status; people suspected that the FBI might have been protecting him.

“Although there are those who have doubted our resolve at times over the years, it has never wavered,” said Richard DesLauriers, special agent in charge of the FBI’s Boston office, during a news conference.

The arrest has sparked mixed emotions in those who grew up during Whitey’s reign. Some are ecstatic at his arrest, including many of the victims’ families, others are angry.

“Well, I don’t know what the exact emotions are, but I think there are a number of people out there with whom it spark a lot of anger,” Bailey said, referring to the people that Bulger ratted out during his time as an informant.

John Ahearn, 66, a former resident, said he was never too afraid of Whitey.

“Sometimes, back then, I had a lot to go with the gang members when I hung out at the bowling alleys. They were nice guys, but they were wise guys. They were very discreet guys. I think some of them were Winter Hill,” Ahearn said.

“The Winter Hill gang, they were particularly a rough gang. They were a lot of trouble. The other guys were just booking guys,” Ahearn remembered. “In the winter hill area, if you wanted to do business…[Bulger] used to go in and say I will protect you if you pay me. Every week they used to go around and collect the money. If you didn’t pay, they would send their goons to rob the store.”

Although he never felt particularly affected by Bulger, he new many people who were.

“I knew a guy that used to rob one of [Winter Hill’s] stores. His friends took him out for a ride and they shot him. He was told not to do anything, but he did it any way,” Ahearn said.

Bulger is expected to appear in court in Los Angeles Thursday, and he will likely be returned to Massachusetts for legal proceedings, according to Bailey. Bulger is up against a laundry list of charges of murder, extortion and money laundering.

“I think under the sentencing guidelines he certainly facing a sentence of up to life,” Bailey said.

Although the case seems fairly clear-cut against Bulger, Bailey thinks that his defense might try to use his status as an informant to his benefit.

“I suppose that one of the defenses their going to look at is whether an alleged top echelon informant, whether he was authorized to do the things he was accused of doing,” Bailey said. “The answer is that no informant would be allowed to engage in crimes such as murder, but that would be one of the things they’re going to try to look at. ”

Bailey didn’t have much faith in this defense however. He said that he”express[es] extreme skepticism,” in the defense.

“I guess the rest of it is going after the various cooperators that have connected him to the crimes. That they made things up to protect themselves and their own interest,” Bailey continued.

He also added that Bulger faces murder charges in Oklahoma and Florida, where they may try to pursue the death penalty against him.

About The Author

Brittney McNamara is a Blast Junior Editor

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