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James ‘Whitey’ Bugler writes letter to students that crime doesn’t pay

Convicted crime boss pens letter to teens

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High school history projects rarely get this much attention, but this is far from your average study of the Battle of 1812.

James “Whitey” Bulger – a convicted murderer and former Boston-area crime boss – wrote a handwritten letter dated Feb. 24 from federal prison in Florida to three high school girls in Lakeville, Massachusetts.

He starts off by writing: “I’m sorry but I can’t help you with your school project – There are many people more deserving of your time and interests.”

But it doesn’t take long for the 85-year-old to turn a leaf and confess his remorse to the teens, which is something he has never done before.

“My life was wasted and spent foolishly, brought shame and suffering on my parents and siblings and will end soon – Advice is a cheap commodity some seek it from me about crime – I know only thing for sure – If you want to make crime pay – “Go to Law School,” Bugler wrote in the letter to the girls.

According to The Boston Globe, the three 17-year-olds chose Bugler for their National History Day competition entry on leadership. They wanted an unconventional leader that would be different from others in the competition. They posted his letter on the project’s website, with chronicles of his life as a crime lord.

The Irish-American crime boss ran a successful criminal enterprise of drug trafficking and extortion for years before he was finally caught in 2011. Two years later, Bulger was convicted of participating in 11 murders while running the enterprise that racked up millions of dollars, reports the news outlet. He is now facing two life sentences in prison.

“It wasn’t what we were expecting at all,” Brittany Tainsh, who received the letter in her mailbox, told The Boston Globe. “He did not really reply to any of our actual questions. He was very apologetic.”

But not everyone thinks he was remorseful in his letter.

Patricia Donahue, whose husband was killed by Bulger, told the Globe she didn’t think the letter expressed any sorrow for his victims.

“I don’t think he’s changed at all,” she said.

Although the girls’ project didn’t get first place at the state level, they did end up winning two awards – one for best use of primary sources and the other for best project on Massachusetts history.