Whitey Bulger has regrets. That much is clear from a handwritten letter the 85-year-old former mobster sent to a high school student in Lakeville, Massachusetts, several months ago. Brittany Tainsh, one of several teenagers working on a school project around the idea of "leadership," wrote to Bulger this past winter asking him to reflect on his own (admittedly troubled) legacy. From his federal prison cell in Sumterville, Florida, Bulger sat down at 1:10 a.m. with a pen and a sheet of loose leaf and, however briefly, let his mind wander. Here's a full transcription of the letter, courtesy of The Boston Globe (emphasis ours):

Feb. 24, 2015

1:10 a.m.

Hello, Brittany:

I'm sorry but I can't help you with your school project — There are many people more deserving of your time and interests. I'm a myth created by the media to help them generate Revenue and to hurt a relation because they didn't appreciate his independence and daring to support an agenda they opposed.

May I suggest you and Molly create a website about the heroic service men of Mass. that are patients in, for instance, Walter Reed Veteran Hospital — good men isolated from society due to war wounds — life for some in pain and loneliness — hearing from school girls that care would do wonders for their morale and recovery.

Don't waste your time on such as I — we are society's lower, best forgotten, not looked to for advice on "Leadership". I'm a 9th grade dropout from school and took the wrong road — my brother 5 years younger applied himself in school and worked hard and spent 40 years in Mass State House and retired and was the President of Mass Senate in State House for second term and President of U. Mass after Retirement. Had 9 children all college graduates and 4 lawyers among them. A Better Man than I.

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."

Brittany Best of Luck in the future to you and Molly and Michaela.

Sincerely James Bulger

Come September, Bulger will be the subject of what looks like the next great mob movie, Black Mass. He'll be played by Johnny Depp. Watch the chilling trailer here.

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John Hendrickson
Deputy Editor

John Hendrickson is the Deputy Editor of Esquire.com, where he oversees the site's 24/7 news operation as well as all politics coverage.