‘My life was wasted’: Whitey Bulger once penned a letter to three teens about his regrets

In the years leading up to his death, notorious Boston mob boss James “Whitey” Bulger wrote about his regrets in life.

Bulger, imprisoned for life for his role in 11 murders, penned a letter to three teenage girls in 2015, telling them that he was “a 9th grade dropout” who “took the wrong road.”

The former mobster said he was among “society’s lower, best forgotten” members. He told the students, who had first written to him for a project for National History Day, not to spend their time on him.

“My life was wasted and spent foolishly, brought shame and suffering on my parents and siblings and will end soon,” he wrote, according to The Boston Globe.

The Bureau of Prisons confirmed that Bulger, 89, died Tuesday after he was found unresponsive at a penitentiary in Bruceton Mills, West Virginia.

The three high school students — Michaela Arguin, Mollykate Rodenbush and Brittany Tainsh, then juniors in Lakeville, Massachusetts — decided to build their project around Bulger, the former boss of Boston’s notorious Winter Hill Gang. Arguin said that the theme was leadership and that, rather than choosing a positive leader, they chose a negative one, asking Bulger what he thought about his own legacy.

Bulger, no doubt, had a troubled life.

As The Washington Post reported, Bulger, from a poor family in Boston, started stealing when he was young. By the 1950s, he was robbing banks.

By the 1970s and 1980s, he was heading his infamous gang, known for fixing horse races, among other crimes.

The Post continued:

“Although notorious in Boston, Mr. Bulger was largely unknown to the wider world until after he disappeared in 1994. In his absence, his darkest secrets, including his corrupt ties with FBI agents, were gradually laid bare in court hearings, media exposés and a congressional inquiry. He became a nationwide curiosity, sharing space with Osama bin Laden on the FBI’s 10 Most Wanted list.

“Captured in Santa Monica, Calif., in 2011, Mr. Bulger was sentenced to two consecutive life terms plus five years after a Boston jury convicted him of 31 racketeering offenses. The indictment against him cataloged 19 alleged murders, and he was found guilty of ordering or carrying out 11 of them.

“The verdicts, in 2013, climaxed a gangland opera of fealty and betrayal that spanned half a century and combined two of Boston’s abiding fixations: ethnic crime and politics.”

But on Feb. 24, 2015, Bulger replied to the students’ letter from federal prison in Sumterville, Florida, declining to participate and urging the teenagers to find a “more deserving” subject, such as a wounded service member.

“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,” he wrote.

Bulger also talked about his brother, William Bulger, whom he called “A Better Man than I.”

His brother was a former president of the Massachusetts Senate as well as the University of Massachusetts — but was pressured by then-Gov. Mitt Romney to resign from the university in 2003.

Arguin, one of the students who wrote to Bulger, said in 2015 that his response was “shocking.”

“It was a completely different side to what he shows to everyone else,” she told The Boston Globe at the time. “It was kind of weird we kind of had an impact on him, three high school girls. You wouldn’t expect that.”

But more than three years later, Arguin said she feels the same way.

“Looking back now, we honestly, truly reached out to try to gain a primary source for our project and never thought he would respond, let alone the broader implications this response has had about the historical understanding of Whitey today,” she told The Post on Tuesday after the news that Bulger had died in prison.

Arguin, 20, a double-major in political science and Islamic civilization and societies at Boston College, said the fact that Bulger expressed his views to the students was “unique” but what she found interesting was the way that he characterized his remorse.

“He felt badly about how he affected his family’s reputation,” she said, “but not for the families of the victims whose lives he took.”

Still, Arguin said, she was most stuck by his advice.

Bulger had told the students, “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.’ ”

“It’s something you wouldn’t think a mob boss would say,” Arguin said.

Arguin, who said she is a pre-law student, said she has taken Bulger’s suggestion and plans to go to law school — perhaps to study criminal law.