When three Massachusetts high school students wrote to crime leader James "Whitey" Bulger in jail—where he's serving two life sentences (plus five years) for racketeering, money laundering, extortion, and murdering 11 people— they weren't sure if he'd write back. But he did, and the tone of his letter surprised them, mainly due to the fact that, as the Boston Globe puts it, his "unwavering defiance has seemingly been replaced by regret, and even a little remorse." "My life was wasted and spent foolishly, brought shame and suffering on my parents and siblings, and will end soon," he writes, per the Globe. "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."
That "relation" is assumed to be his brother, William Bulger, an ex-state Senate member and former president of the University of Massachusetts, who wouldn't testify against Whitey at his trial, the Globe reports. The letter sent by the 85-year-old from a Sumterville, Fla., prison to 17-year-olds Brittany Tainsh, Michaela Arguin, and Mollykate Rodenbush, juniors at Apponequet Regional High School, was his response to a letter they sent as part of a National History Day contest about leadership; they chose Bulger as the subject of their entry because he wasn't a conventional heroic leader. "Don't waste your time on such as I—we are society's lower, best forgotten, not looked to for advice on 'Leadership,'" he writes in his reply. "I’m a 9th grade dropout from school and took the wrong road." Instead, he tells the girls to redirect their efforts to wounded service men in a VA hospital and mentions that "if you want to make crime pay—'Go to Law School.'" (Read more Whitey Bulger stories.)