James “Whitey” Bulger showed no mercy to the people he tortured and killed. He refused to get on his knees when captured after more than a decade on the run because he didn’t want to get his pants dirty. And he swore at witnesses during his trial.

Now, as the imprisoned 85-year-old gangster faces the end of his life, his unwavering defiance has seemingly been replaced by regret, and even a little remorse. At least that’s what he told three local high school girls.


“My life was wasted and spent foolishly, brought shame + suffering on my parents and siblings and will end soon,” Bulger wrote in a Feb. 24 letter sent from a federal penitentiary in Sumterville, Fla.

“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.’ ”

Bulger wrote that he “took the wrong road,” in stark contrast to his younger brother, William Bulger, former president of the state Senate and the University of Massachusetts, whom he called, “A Better Man than I.”

The unprecedented confession letter from the former South Boston crime boss — whose taxpayer-funded defense topped $3 million — was sent not to a priest or the relatives of any of the 11 people he killed, but to several 17-year-old juniors at Apponequet Regional High School in Lakeville.

The students created a website about Bulger for a National History Day competition on leadership and legacy and wrote to the octogenarian last February, seeking his opinion on his own legacy.


“It wasn’t what we were expecting at all,” said Brittany Tainsh, who was stunned when Bulger’s letter arrived in her mailbox, among a flurry of college brochures. “He did not really reply to any of our actual questions. He was very apologetic.”

Tainsh and her classmates, Michaela Arguin and Mollykate Rodenbush, said they chose Bulger for their project because he was a leader — albeit a brutal organized crime leader — and they wanted to do something unconventional that would set them apart from others in the competition who chose heroes and presidents.

A copy of the letter James “Whitey” Bulger sent to the three teens. David L Ryan, Globe Staff

They posted Bulger’s letter on the website they created, which chronicles his life as a gangster, FBI informant, fugitive, and convicted killer. He was captured in Santa Monica, Calif., in 2011 after more than 16 years on the run, and convicted two years later in federal court in Boston of participating in 11 murders in the 1970s and 1980s while running a sprawling criminal enterprise that raked in millions from drug trafficking and extortion.

Bulger’s letter did not sound remorseful or conciliatory to Patricia Donahue, whose husband, Michael, was shot to death by Bulger in 1982 while giving a ride home to a friend who was the gangster’s intended target.

“I don’t think he’s changed at all,” Donahue said, noting that Bulger’s letter only referred to the suffering of his own family, not that of his victims or their families. “All he cares about is his family, which is probably one of the only normal things about him. He doesn’t care about anybody else. I’m sure he doesn’t have any remorse about anyone he’s hurt or killed.”


But Donahue did agree with at least one thing he wrote.

“He is a wasted life,” she said.

Bulger’s lawyer, Hank Brennan, declined to comment on the letter or Bulger’s frame of mind.

A federal appeals court is scheduled to hear arguments July 27 on Bulger’s request to have his 2013 conviction overturned. He is currently serving two consecutive life prison terms.

Bulger’s one-page missive, which notes at the top that it was penned at 1:10 a.m. on Feb. 24, is handwritten. The tiny cursive letters stay neatly on the white-lined paper and he uses capital letters, quotation marks and long dashes to make his points — though little other punctuation.

He complained that he is “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.”

The line is an apparent reference to William Bulger, who was pressured in 2003 by Governor Mitt Romney to resign as UMass president after being grilled by a congressional committee about his relationship with his gangster brother.

“It wasn’t what we were expecting at all,” said Brittany Tainsh, who was stunned when Bulger’s letter arrived in her mailbox. David L Ryan, Globe Staff

In his letter to the students, Bulger, who reportedly prides himself on being patriotic, suggested that instead of focusing on him, the girls should create a website for wounded American servicemen: “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 + recovery.


“Don’t waste your time on such as I — we are society’s lower, best forgotten, not looked to for advice on ‘Leadership,’” Bulger wrote.

The aging gangster also wrote that he dropped out of school during the ninth grade and “took the wrong road,” while his brother William, the politician, worked hard, rose to the top of the Massachusetts Senate, and raised nine children who all graduated from college, including four who became lawyers.

“It was a completely different side to what he shows to everyone else,” Arguin said. “It was kind of weird we kind of had an impact on him, three high school girls. You wouldn’t expect that. It was really shocking.”

Rodenbush said the depressing tone of Bulger’s letter was startling because she and her classmates had not seen that side of him during their research.

“I think the most interesting aspect of the letter is that he was almost regretful and nostalgic, but not in a positive way,” Rodenbush said.

The girls’ website on Bulger took first place in the district competition, but failed to place at the state competition, where a website about journalist Nellie Bly came in first.

However, they won two special awards, one for best use of primary sources and the other for best project on Massachusetts history.

Robert Powers, a social studies teacher at Apponequet Regional High who oversees the school’s entries into the National History Day competition, said the girls took a creative risk by focusing their website on Bulger, and were successful even though they didn’t win.


“They have contributed to our historical understanding of Whitey Bulger, and to me, that’s what this program is all about,” Powers said.

Tainsh, Arguin, and Rodenbush said they learned a lot by focusing on someone they did not study in school, who has had a huge impact on Boston and the FBI.

“If we picked a dead president, we wouldn’t have got a letter,” Arguin said. “Nobody else in the entire competition had a letter [to them] from the person they did the project on.”

Retired Massachusetts State Police Colonel Thomas Foley, who spearheaded the Bulger investigation, said the letter suggests the gangster is only remorseful that he ended up in prison.

“He doesn’t feel bad for the victims or anyone else,” Foley said. “All he feels bad for is himself. It’s typical Whitey.”

Shelley Murphy can be reached at shmurphy@globe.com. Follow her on Twitter @shelleymurph.