James 'Whitey' Bulger dead: History of notorious gangster's life

BOSTON — For most of us, our first glimpse of the elusive South Boston mob boss James Whitey Bulger was in federal prison orange, escorted under heavy guard on his way to a federal court hearing in Boston.

The man who was once the most feared name in Boston's underworld, reduced to a perp walk. 
James Bulger was born September 3, 1929, in Dorchester. He was one of six children in a Roman Catholic family and grew up in the South Boston projects.

Bulger’s first brush with the law was at the age of 14, setting up a lifetime of being on the wrong side of the law.

Before that side of his life, Bulger served in the United States Air Force. He received an honorable discharge in 1952 and that's when it all turned into a life of crime.

There were arrests for bank robberies and other crimes, a stint in a federal pen where Bulger volunteered for an LSD experiment in return for early release.

Bulger did time in Alcatraz; America’s future most wanted fugitive, housed in America's most notorious prison.

Finally, in 1965, James Bulger returned to the Boston area and inserted himself as a member of the Winter Hill gang, directly into what's become known as the deadly Irish gang wars.

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Bulger eventually took over the Winter Hill gang in Somerville from Howie Winter and that's when Bulger and his cohort Steven Flemmi moved their headquarters from Somerville to Lancaster Street and that's where the state police shot the infamous surveillance video.

That very location brought the Bulger gang close to the Italian mob's North End turf of the Anguillo family and soon enough, Bulger and Flemmi, according to court proceedings, became secret FBI informants. Their handler was FBI agent John Donnelly. It was an unusual relationship between an FBI operative and his informants and turned criminal. Connelly was convicted in 2002 on racketeering charges stemming from his relationship with Bulger.

The DEA started to put the heat on Bulger and that's when Whitey started living his life as a fugitive from justice. Along for the ride, his longtime girlfriend Theresa Stanley.

Stanley didn't last long; she wanted to go back with her kids.

Enter Catherine Greig. Twenty years younger than Bulger and had plenty of history with him. She’s believed to be his lover while he was with Stanley.

Nobody knew where they were. There were plenty of guesses, plenty of sightings. For 16 years this couple somehow eluded authorities.

Whitey was on the FBI's Most Wanted list the entire time with a million-dollar bounty on his head.

And then, the unbelievable.

A PSA was released by the same agency, that cut a deal with Whitey.

The FBI focused on Catherine Greig. They thought if someone recognized her or if somehow she got word that that would lead them to Whitey.

And they were right. It did.

But not in the states, in Iceland

A woman who used to live in Santa Monica, California recognized Catherine.

The FBI says she contacted them from her new home in Iceland and the rest is history.

An alleged mobster from South Boston, sitting on the FBI's Most Wanted list for so many years, was found living in California in a tiny apartment under the names Charles and Carol Gasko. Controlling his environment, his girlfriend, his world - until the FBI was able to lure him out of his apartment under a ruse and went in for the arrest.

The date, June 22, 2011.

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Greig was convicted and sentenced to prison for eight years after pleading guilty to conspiracy to harbor a fugitive, identity fraud and conspiracy to commit identity fraud.

Bulger sat at the Plymouth County House of Correction waiting for the trial of his crime, which started two years later in June of 2013. He faced 32 counts of racketeering, money laundering, extortion, and weapons charges, including complicity in 19 murders.

August 12, 2013, Whitey Bulger was found guilty on 31 counts, including both racketeering charges, and was found to have been involved in 11 murders.

Bulger was sentenced to two consecutive life terms plus five years for his crimes.

Bulger's assets were auctioned off in June of 2016, raising $109,000 for his victims.

Bulger's life of crime caught the attention of Hollywood. The character of Frank Costello, played by Jack Nicholson in the 2006 Martin Scorsese film The Departed, is loosely based on Whitey and Johnny Depp took on the role as the mob boss in the film Black Mass.

Cox Media Group