Study Guide

Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Criminality

By Dick Lehr and Gerard O'Neill


You think Biggie Smalls was a true OG? The Notorious One doesn't have anything on Whitey Bulger.

One of the most brutal gangsters ever seen in the Irish-American hood of South Boston, Bulger rules the city's criminal underworld for decades. Of course, he has a little help from his friends: a few corrupt FBI agents, for one.

Aided by his G-men pals, Bulger stacks up a body count that would make Voldemort jealous, dominating everything from drugs to gambling to vending machines. He might be a criminal, but the Whitey portrayed in Black Mass sure isn't common.

Questions About Criminality

  1. Can John Morris and John Connolly be considered criminals? Defend your position.
  2. In what ways does Whitey Bulger differ from an ordinary criminal?
  3. Can Bulger truly be considered a "chessmaster" of crime? Explain.
  4. Is Steve Flemmi an effective informant? Why or why not?

Chew on This

Bulger can be considered a "chessmaster" when it comes to crime: he exploits the FBI's informant deal to its maximum benefit.

Bulger can't be considered a "chessmaster" when it comes to crime: he simply lucks into the best FBI informant deal of all time.