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James “Whitey” Bulger: I “Took The Wrong Road”

Former South Boston crime boss James "Whitey" Bulger, convicted in 11 killings and other crimes during the 1970s and '80s, has expressed remorse and regret about his life in an unprecedented letter to three high school girls in Massachusetts.

In the letter, Bulger tells the juniors from Apponequet High School in Lakeville that he wasted his life and spent his days foolishly.

The students wrote to Bulger, seeking his opinion on his own legacy for a National History Day competition. They created a website to compete, and were shocked when they got his response.

"We decided to do a negative leader, so someone who is different from a president or a positive role model," said one of the teens, Michaela Arguin.

"My life was wasted and spent foolishly, brought shame + suffering on my parents and siblings and will end soon," Bulger wrote in the letter, dated Feb. 24. 

Bulger goes on to say that he "took the wrong road."

"From strictly just looking at the letter, it does seem like he has had a little bit of a turnaround, sitting in jail for so long," said student Brittany Tainsh.

But legal analyst Margaret McLean says the letter is far from an apology.

"I think he's waging his own media campaign in the press for the sake of the Bulger family name and his own reputation," she said. "I think he's been doing this since the time of the trial."

McLean says Bulger needs to improve his image ahead of his appeal set for next month.

But she agrees that the letter had one sound piece of advice for teenagers.

"Advice is a cheap commodity some seek it from me about crime — I know only one thing for sure — If you want to make crime pay — 'Go to Law School,'" the letter read.

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