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I-Team: Letters Written By ‘Loving’ Whitey Show Bond Between Bulger Brothers

By Kathy Curran, WBZ-TV
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WBZ-TV's I-Team obtained several never before seen photos of James 'Whitey' Bulger,  including tihs passport photo.

WBZ-TV’s I-Team obtained several never before seen photos of James ‘Whitey’ Bulger, including tihs passport photo.

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BOSTON (CBS) – With Whitey Bulger finally in custody, interest in the relationship with his brother, William Bulger, is intensifying.

Now there’s a new window into that secretive relationship and it’s all in letters, never seen before and obtained by the I-Team, that Whitey wrote to his brother from prison.

In letter after letter penned by the Mob Boss himself, written in elegant script, Whitey Bulger writes to his younger brother Bill and his mother while serving time in federal prison back in the late 1950’s.

The letters are signed “Jim,” “Whitey” and “Big Brother.”

Bulger was just 26 years old when he was convicted of robbing banks in Melrose, Rhode Island and Indiana. He did nine years in four federal penitentiaries, including Alcatraz, yet always found time to write to Bill.

WBZ-TV’s Kathy Curran reports.

In those letters, Whitey dotes on his little brother, urging him to “keep studying,” “stick with the books,” and “don’t worry about writing so often.”

“It’s brotherly love, brotherly love, and it goes deep,” said Bob Long, a retired State Police detective who was one of the first to investigate Whitey Bulger in the early 1980’s.

Photos: The Whitey Bulger Scrapbook

We showed the letters to Long and he was fascinated. Asked if he thought the man who wrote those letters could go on to commit the murder and mayhem Whitey Bulger’s been accused of, Long said: “If I read those letters back then, no.”

In one letter, commenting on a photograph of Billy he received from home, Whitey told his brother he looked “nifty” in his suit, like something “out of Esquire.”

In another, Whitey actually urges his brother to pursue a career in politics as it “pays a good salary” and “a pension.”

The bond between the brothers began in the South Boston projects, where the Bulgers grew up, and it appears that bond remains strong to this day, evidenced by the smiles they exchanged in a U.S. District Court in Boston after Whitey’s capture.

Back in the early days the letters reveal that William was Whitey’s confidante.

In one letter, Whitey tells his brother that “talking about Boston” makes him “homesick.” But as the years in prison wore on, Whitey wrote that thinking of his hometown became “bad medicine.” “My interest in Boston… has completely died,” he wrote.

Whitey admitted he “never hit it off” with their father, whose health was declining at the time, and regretted “all the heartache I caused him.”

In letters to his mother, he paints a rosy picture of prison life, writing: “I’m doing pretty well,” “still at my same job,” and my “weight [is] 165.”

Just before New Year’s in 1957, Whitey wrote about making some resolutions to settle down and make the best of prison life, where there were “no late hours, whiskey, women or fast cars” to distract him.

“Monsters can be very loving to those they care about,” said James Fox, a criminologist at Northeastern University. “The public persona of Whitey Bulger is not that of a loving individual. It’s of a monster, of a controlling, aggressive, manipulative crime boss. But even a controlling manipulative crime boss can be loving and caring at home.”

And in one letter, Whitey even wrote about wanting to come home to South Boston after prison and settle down. Everyone knows that didn’t happen.

Instead, Whitey Bulger began a reign of terror that lasted decades.

William Bulger would not comment on the letters.

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