Whitey And Billy: A Tale Of Two Boston Brothers

LEFT: June 2011 booking photo of James “Whitey” Bulger (U.S. Marshals/AP) RIGHT: Former Mass. Senate President William Bulger is escorted from the federal courthouse after the first appearance for his brother James “Whitey” Bulger in Boston, June 24, 2011. (Charles Krupa/AP)

LEFT: June 2011 booking photo of James “Whitey” Bulger (U.S. Marshals/AP) RIGHT: Former Mass. Senate President William Bulger is escorted from the federal courthouse after the first appearance for his brother James “Whitey” Bulger in Boston, June 24, 2011. (Charles Krupa/AP)

BOSTON – Jury selection begins this week in the trial of notorious Boston mobster James “Whitey” Bulger, who is accused of killing 19 people.

Part of Whitey Bulger’s mystique has long been his little brother. During the years when Whitey ruled the underworld, his younger brother, Bill, ruled the political world.

William Bulger was president of the Massachusetts Senate for 18 years, far longer than anyone in the state’s history. Whitey Bulger, on the other hand, was one of the FBI’s most wanted.

And yet, the siblings were inextricably connected. The two brothers once held the reins to this city.

A Trip Down Memory Lane

To a newcomer, South Boston glitters like a yuppie heaven. When you see the luxury condos and trendy restaurants on the streets of old Southie, it’s hard to imagine that once upon a time, in the not-so-distant past, this was a really rough patch of town.

It was in the Old Harbor Housing Projects of South Boston where both brothers got their start.

“The Bulger brothers were the twin pillars of reality,” said Peter Gelzinis, a South Boston native who has spent years covering the Bulger saga for The Boston Herald.

“Billy controlled the politics in a very, very, very political neighborhood. And Whitey controlled the streets in a very tough neighborhood,” Gelzinis added.

Similar Traits?

Bill Bulger was a stellar student who studied Greek and Latin and graduated from Boston College Law School.

Older brother Whitey was a bank robber, a thug who served time in Alcatraz.

As different as they seem, the brothers shared “personality traits,” said Dick Lehr, an author of two books about Whitey Bulger and a former Boston Globe reporter.

“They’re both very tough in their respective fields. Whitey Bulger was a stone cold killer. He’s a master chess player in the game of life in the underworld,” said Lehr.

His little brother was another story.

“Bill Bulger was a master at the exercise of political power. You didn’t mess with Bill Bulger. People were frightened of him, politically speaking,” said Lehr.

Bill Bulger knew he inspired fear in others. In a 1992 “60 Minutes” interview, he described himself as an “autocratic, dictatorial boss.”

“Bill Bulger was a very effective politician and a very effective Senate president,” said Warren Tolman, who served in the state Senate with him. He was part of a crew that tried — and failed — to oust the powerful Senate president.

“He knew how to count. And, in a positive sense, he knew…there were 40 members of the Senate. He knew how to get to 21,” said Tolman.

Tolman said fellow politicians feared political repercussions if they stood up to Bill Bulger. But, no, they never feared physical retaliation from his brother Whitey.

“There was a sense then that these two brothers had taken dramatically different paths,” said Tolman.

Family Ties

And, yet, Brother Bill could never truly separate himself from Whitey. Dick Lehr said that’s because of their ultimate family loyalty.

“These guys have had each other’s back going back to…the bedroom they shared in the Old Harbor Housing Project. They’ve been close forever,” said Lehr.

During the “60 Minutes” interview, Bill Bulger was asked about his brother. And he, again, showed his devotion.

“He’s my brother, I care about him,” he said. “I encourage him to come by all the time.”

That was three years before Whitey Bulger went on the lam.

In 2003, Bill Bulger found himself testifying on Capitol Hill about his brother’s disappearance.

“I do not know where he has been over the past eight years, I have not aided James Bulger in any way while he has been a fugitive,” Bill Bulger told a congressional committee.

But that wasn’t an adequate defense: Bill Bulger lost his job as president of the University of Massachusetts.

These days, Bill Bulger is still sticking by his brother. He was at Whitey’s arraignment and is expected to be a regular in the courtroom during the trial of the summer.

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  • NYBamBam

    That was kind. Billy Bulger was a thief, who used his offices (and the implicit threat, inherent in his brother’s role as a gangster) to shake down Boston and Springfield building developers. When Whitey’s corruption of the FBI met, yet another ethics investigation into Billy’s criminal behavior, the state legislature hijacked the UMass president’s hiring process and installed Billy as head of UMass.

    Where upon he looted the offices for his own benefit, and blew 300M on IT renovations dripping in corporate conflict of interest relationships. Think about that, next time you open up a bill from UMass and get sticker shock. Billy and Whitey were gangsters, they just worked different sides of the street. But they were always on the same side.

    • Dorkko

      I can’t speak to any of that but I can say that his apparent support for his brother says something about his own personality. If I had a brother who was a gangster-killer to say that we were estranged would be a gross understatement. Family and ethnicity have nothing to do it. I come from a close nit Italian-American family.

      • NYBamBam

        I can understand brotherly loyalty – I grew up in the predominantly Scilian-American borough of Staten Island – but these guys were in business together, working different sides of the street toward the common goal of accumulating power and wealth.
        I look forward to the trial of Billy Bulger and everyone he sponsored or worked with. Only then will my trust in that corrupt, elitist and corporatist sewer we call Boston politics stop disintegrating.

        • Dorkko

          They’re both psychopaths.

          • NYBamBam


  • icekreaman

    why r people so obsessed with these guys? 40 years from now will we be reading romanticised books and watching glorified movies about the many gang related killings in Roxbury and Dorchester…?

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