A high school history lesson – from Whitey Bulger?

Former Boston crime boss Whitey Bulger wrote to three Massachusetts high school students doing a history project. Why would Bulger's perspective matter?

When you’re serving two consecutive life sentences, it’s probably easy to find time to write a letter or two.

Convicted former mob boss James “Whitey” Bulger, now in a high-security Florida prison, proved that when he responded to three Massachusetts high school students who wrote him as part of their submission for a National History Day competition on the themes of leadership and legacy.

The exchange put a spotlight both on Mr. Bulger’s current frame of mind and on what historical value convicted criminals or otherwise controversial persons might have for young people today.

“My life was wasted and spent foolishly, brought shame + suffering on my parents and siblings and will end soon,” Bulger wrote in the Feb. 24 letter, first published by the Boston Globe.

The ex-crime boss and FBI informant, who was a prominent figure in the Boston mob scene for 20 years and found guilty of extortion, conspiracy, and 11 murders in 2013, went on to say that he “took the wrong road.”

He suggested that the students focus their leadership and legacy project on veterans, " ... 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."

“Don’t waste your time on such as I,” he continued. “I know only [one] thing for sure. If you want to make crime pay – ‘Go to Law School.’”

For some, the letter was a further sign of Bulger’s incorrigibility.  

“He doesn’t feel bad for the victims or anyone else,” retired Massachusetts State Police Colonel Thomas Foley, who spearheaded the Bulger investigation, told the Globe. “All he feels bad for is himself. It’s typical Whitey.”

Patricia Donahue, the widow of one of Bulger’s victims, agreed: “I don’t think he’s changed at all,” she told the Globe. “All he cares about is his family… I’m sure he doesn’t have any remorse about anyone he’s hurt or killed.”

Aside from reviving discussion of Bulger’s personality a month before he is scheduled to appeal his conviction, however, the exchange raises questions: What lessons could a convicted criminal give on leadership or legacy? What value is there in giving students access to such a person’s perspective?

One answer may lie in what some educators call historical thinking – looking at the events and people of the past with a critical and questioning mind instead of taking a single narrative for granted as fact. Advocates of the concept encourage students’ exposure to primary documents, various sources, contextual information, and multiple accounts and perspectives.

“Real historical understanding requires that students have opportunity to create historical narratives and arguments of their own,” reads an introduction to the standards of historical thinking from the University of California Los Angeles’ history department.

Professors of history Flannery Burke and Thomas Andrews, in an article for the American Historical Association, wrote that the idea is to “help students to see the past not simply as prelude to our present, nor a list of facts to memorize, a cast of heroes and villains to cheer and boo, nor as an itinerary of places to tour, but rather as an ideal field for thinking long and hard about important questions.”

Whitey Bulger, for better or worse, is a part of both Boston and American history. For at least one faculty member at Apponequet Regional High in Lakeville, Mass. – where the three girls who wrote to Bulger are juniors – the students’ decision to focus on the former mob boss showed creative risk and they were successful even though they didn’t win the state competition.

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