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Whitey Bulger Remorseful? Ex-Mob Boss Writes Heartfelt Letter To Teens About Life Of Crime

By Toni Matthews
Published on: 22:34 PST, Jun 28, 2015

Whitey Bulger seems to regret his criminal ways. In a letter to several teens, the former Boston mob boss said that his life was “wasted” and “spent foolishly.” He advised the three girls that there was only one way to truly make crime pay — Law school.

The infamous James “Whitey” Bulger is in the early stages of a life sentence, brought on by acts ranging from racketeering to cold-blooded murder. Despite his role as an FBI informant, the Irish mobster had a hand in 11 deaths. Whitey’s criminal career lasted from the ’70s into the ’90s, but when his wicked deeds began to catch up with him, Bulger fled. After spending 16 years on the run from law enforcement, he was finally captured in 2011. Two years later, he was successfully convicted and sent to prison.

Now 85, Whitey Bulger has had a chance to reflect on his life, and he doesn’t seem to be very proud of it. In the letter, he mentioned that his life “brought shame and suffering on [his] parents and siblings”. He also remarked that it will “end soon,” as he is to spend the last of his natural life behind bars.

The letter was an admitted surprise to the three teens who wrote to Whitey Bulger as part of a school project. The trio took a less than conventional approach to the subject of “leadership and legacy” as part of a National History Day competition to set themselves apart. The teens reached out to Whitey in a letter but never imagined he would actually write back.

Seventeen-year-old Brittany Tainsh said that Bulger didn’t answer any of the questions they asked, but he was “very apologetic”. The remorseful response to Tainsh and her classmates Michaela Arguin and Mollykate Rodenbush was also something of a surprise. With his bloody criminal career a matter of public record, he could have owned it and even bragged a bit for the star-struck youngsters. However, the message was clear.

“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'”

Although Whitey Bulger hoped his letter would warn the teens and other young people about seeing him as any kind of leader or hero, there continues to be enough of a fascination to at least warrant a website about him. The Whitey website, managed by the teens, reportedly chronicles his entire criminal history.

It also features a copy of the letter Whitey Bulger wrote them.

[Image Credit: U.S. Marshals/Wikimedia Commons]

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