This 1953 Boston police booking photo shows James “Whitey” Bulger after an arrest. Bulger and his girlfriend Catherine Greig, were apprehended June 23, 2011, in Santa Monica, Calif., after 16 years on the run. (Boston Police via AP)

Notorious Boston mobster James “Whitey” Bulger, an 85-year-old inmate currently serving out two life sentences for his role in 11 murders, recently penned a letter to some teenage girls from prison, telling them he wasted his life.

“My life was wasted and spent foolishly, brought shame and suffering on my parents and siblings and will end soon,” he wrote. “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.'”

Three teenage girls from Apponequet Regional High School in Lakeville, Mass., sent Bulger a letter for a recent National History Day competition about leadership. The girls — Michaela Arguin, Mollykate Rodenbush and Brittany Tainsh — said they picked him for their project because they wanted their entry to stand out.

In the wee hours on Feb. 24, Bulger replied, writing thoughts on a piece of notebook paper. He mailed the letter from a federal prison in Sumterville, Fla.

“It wasn’t what we were expecting at all,” Tainsh told the Boston Globe. “He did not really reply to any of our actual questions. He was very apologetic.”

Bulger told the teens he couldn’t help them with their history project.

“There are many people more deserving of your time and interests,” he wrote. “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.”

Instead, he told them, they should do their project on wounded 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 and recovery,” he wrote.


A June 19, 2015, photo shows a letter received from Whitey Bulger by three Apponequet Regional High School students in Massachusetts who wrote to Bulger for a history contest on leadership and got a surprising letter back. (Boston Globe via AP)

Bulger dropped out of high school in the ninth grade, he said, and “took the wrong road.” In the 1970s and 1980s, he was a Boston crime boss, heading the city’s infamous Winter Hill Gang, known for drug-trafficking, murder-for-hire and illegal gambling — namely, fixing horse races.

For 16 years, he topped the FBI’s Most Wanted List. Authorities caught up to him in 2011 in Santa Monica. In 2013, he was convicted for 11 killings as well as racketeering and gun possession.

Bulger’s case gained national attention. His brother, William Bulger, was a former president of the state Senate as well as the University of Massachusetts. But because of Bulger’s reputation, William was asked by Gov. Mitt Romney to resign from the university in 2003, according to the Boston Globe. Bulger recently told the teens who wrote to him that his brother was “a better man than I.”

“Don’t waste your time on such as I,” he wrote. “We are society’s lower, best forgotten, not looked to for advice on ‘leadership.'”

Retired Massachusetts State Police Col. Thomas Foley, who led Bulger’s investigation, told the Boston Globe that the letter only shows that Bulger is sorry to be behind bars.

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

A federal appeals court is expected to hear an appeal request from Bulger on July 27, according to the Boston Globe.

Robert Powers, who is in charge of the school’s entries in the competition, told the Boston Globe that although the students had taken a risk with their project, “they have contributed to our historical understanding of Whitey Bulger, and to me, that’s what this program is all about.”

The students won the district competition but did not place at the state level. The winner was a project on 19th century journalist Nellie Bly.


From left: high school students Mollykate Rodenbush, Brittany Tainsh, and Michaela Arguin, hold a letter on June 19 from former Boston crime boss James “Whitey” Bulger in Lakeville, Mass. (David L Ryan/Boston Globe via AP)