Book Club Discussion Questions: Black Mass


  1. Grade the book, A-F
  2. What are your overall impressions of the FBI after reading this book?
  3. What were some of the pros and cons of Gerard K. O'Neill and Dick Lehr's writing styles?
  4. Bulger notably befriended many in the South Boston community and beyond.  How do you think he covered the bases with informants in training them to follow his methods of madness?
  5. Connolly was essentially enamored with Bulger and his artful ways.  If you were him as a young agent, would you feel the same way?  Why or why not?
  6. As we know, the Showtime show, Ray Donovan, is based on the life of Whitey.  What similarities/differences do you notice between that and Black Mass as two interpretations of his life?
  7. Do you think any parts of the book would have been written differently if it had been written after Whitey was caught or put on trial?
  8. Has Whitey's story and reputation been glamorized?
  9. Do you think the city and state are still corrupt? If not, what has changed about our city's culture in the past 20 years to prevent these situations?
  10. A lot of Whitey & Flemmi's schemes had to do with gambling and betting; Do you think a new casino in Everett would open up the area to similar racketeering schemes in the coming years?
  11. Do you think informants influenced by Whitey are still out there living a lie?
  12. What is one thing about Boston you learned from this book that you didn't know before?


Think we're psyched for the movie next year, or what?!

For more updated information on Bulger after he was found and last summer's trial, be sure to catch the CNN special on Whitey, too (we'll be watching it tonight at book club)!

- Meredith