Winter Hill Gang Headquarters, Boston

By David Posted On Apr 16, 2017

I Walked Boston’S Winter Hill Gang Headquarters – Situated in a parking garage along Lancaster Street in Boston resides what was once the headquarters of Irish organized crime syndicate, the Winter Hill Gang and their former leader James “Whitey” Bulger. The Winter Hill Gang is said to be the basis for the 2006 Martin Scorsese film, The Departed.

The Winter Hill Gang was most noted for having fixed horse races along the East Coast. That is until 1979 when an Atlantic City jockey provided police with evidence necessary to indict members of the Irish crime syndicate. This indictment included Howie Winter himself, and left a vacancy at the top. Not arrested for the crime due to his existing relationship as an informant within the FBI and paving the way for his claim at the top was “Whitey” Bulger.

Bulger obtained his early “career” experience at the age of 14 through larceny and robbing banks for which he spent a number of years in various jails, including the infamous Alcatraz. Known for his platinum blond hair in his younger years it led to him earning the nickname “Whitey.”

When Bulger took over the reigns of the Winter Hill Gang he moved their headquarters to the Lancaster Foreign Car Service parking garage at 131 Lancaster Street. Almost every day around 1:30pm Bulger arrived at this location in his 1979 Chevy Caprice and got down to business.

Winter Hill Gang Headquarters

Winter Hill Gang Headquarters

Under Bulger’s leadership, the Winter Hill Gang re-focused their business model to stay out of activities like race fixing which could be directly traced back to them. Instead they instituted a pyramid scheme of sorts whereby they charged local criminals a “fee” to stay in business. Fail to pay once, it’s a broken bone. Fail twice, well you didn’t. Per the FBI, 18-19 murders have been directly linked to Bulger although for much of this time they turned the other way.

The reason for this was that, as mentioned earlier, Bulger had a “working” relationship with some members of the FBI where he acted as an informant, primarily versus his arch enemies the Italian Mafia. FBI supporters who often tipped off Whitey of any ongoing investigations claimed that information from Bulger helped lead to the eventual arrest of Jerry Angiulo, the head of the Italian Mafia at nearby 99 Prince Street in Boston’s North End. Others in the FBI were less optimistic as to the quality of information provided.

Bulger’s biggest supporter in the FBI was a childhood friend by the name of John Connolly. The tale of how these 2 individuals met is now one of lore. It seems that when Whitey was 19 years old he walked into an ice-cream shop and offered to buy ice cream for three 8-year-old boys in the shop. Only one boy refused stating that his parents had taught him not to accept gifts from strangers. Whitey supposedly looked the kid in the eye and told him, “Hey kid, I’m not stranger. Your mother and father are from Ireland. My mother and father are from Ireland. What kind of ice cream do you want?” The kid grinned and responded, “Vanilla.” That kid was, of course, John Connolly.

Connolly’s relationship with Bulger, long in question, finally came to a head in 1995 when an indictment for Bulger was released. However, when police went to go arrest Whitey he had disappeared with his long-time girlfriend Teresa Stanley. It was figured that Connolly was likely the one who tipped him off. In 1999 Connolly was arrested for obstruction of justice amongst other things and was sentenced to 8-10 years.

In regards to our man on the run, Bulger returned to Boston only one time just a month after eluding police. This stop was supposedly to drop off his girlfriend Teresa Stanley, who had determined that she wasn’t made for life on the run. Whitey, in exchange, dropped her off and picked up another long-term girlfriend Catherine Greig and this time did not return.

Since his disappearance in 1995, Bulger has reported been seen in New York, California, Wyoming, Louisiana, Mississippi and Europe. It’s said while on the run he had used such aliases as Tom Harris, Tom Marshall, Thomas F. Baxter, Mark Shapeton, Jimmy Bulger, James Joseph Bulger, James J. Bulger Jr., James Joseph Bulger, Jr., and “Whitey.” In reference to some of the latter aliases, one has to question how some of these aliases have gone undetected.

Whitey has been on the FBI’s Top Ten Most Wanted List since 1999 and is second only to Osama Bin Laden. His tale had been told on America’s Most Wanted 14 times from 1995 to present and the FBI is currently offering a $2 million award leading to his arrest.

Update: Whitey Bulger was arrested on June 22, 2011 in Santa Monica, CA after having been on the run for approximately 16 years.

Apr 16, 2017 - Posted by David - No Comments

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