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True Crime Book Club - Past Titles: March 2024

Trigger Warning: Take a look through our previous titles from our True Crime Book Club.

"Black Mass" by Dick Lehr & Gerard O'Neill

  1. Collusion between Criminals and Law Enforcement:

    • How did the relationship between Whitey Bulger and the FBI develop, and what factors allowed such collusion to occur?
    • Discuss the ethical implications of law enforcement cooperating with criminals for perceived benefits. How did this compromise the integrity of the justice system?
  2. Motivations and Loyalties:

    • Explore the motivations behind Whitey Bulger's criminal activities. What drove him, and how did his personal history shape his criminal behavior?
    • Examine the motivations of FBI agents who collaborated with Bulger. What were the perceived benefits for both sides, and how did loyalty play a role?
  3. Impact on the Community:

    • How did Whitey Bulger's criminal empire impact the communities in which he operated, particularly South Boston?
    • Discuss the consequences of the FBI's deal with Bulger for the broader community. How did it affect public trust in law enforcement?
  4. Betrayal and Trust:

    • Analyze the theme of betrayal in the book. How did Whitey Bulger betray those close to him, and how did the FBI betray the public's trust?
    • Explore the concept of trust within criminal organizations. How did Bulger use trust as a tool for manipulation?
  5. Legal and Ethical Questions:

    • Discuss the legal and ethical dilemmas faced by law enforcement when dealing with informants like Bulger. Were the actions of the FBI justified from a law enforcement perspective?
    • How did the deal with Bulger complicate the pursuit of justice, and what challenges did it pose for prosecutors?
  6. Media Portrayal:

    • Analyze how the media portrayed Whitey Bulger during his criminal career and trial. How did media coverage shape public perceptions of the case?
    • Discuss the role of the media in exposing corruption within law enforcement and organized crime.
  7. Individual Responsibility:

    • To what extent do you believe individuals within the FBI were responsible for the crimes committed by Whitey Bulger under their protection?
    • Discuss the legal and moral responsibility of individuals within criminal organizations. How does the book explore the concept of individual agency in a larger criminal network?
  8. Lessons Learned:

    • What lessons can be drawn from the story of Whitey Bulger and the FBI's collaboration with him? How can law enforcement agencies prevent similar situations in the future?
    • Discuss any reforms or changes in procedures that may have been implemented as a result of the revelations in the book.

James Joseph "Whitey" Bulger Jr. was an American organized crime boss who became infamous as the leader of the Winter Hill Gang, a criminal organization operating in the Boston area. Born on September 3, 1929, in Dorchester, Massachusetts, Bulger grew up in a working-class Irish-American family.

Here is a brief biography of Whitey Bulger:

Early Life: Whitey Bulger grew up in South Boston, a neighborhood known for its strong Irish-American community. He had several siblings, including his younger brother William "Billy" Bulger, who would later become a prominent political figure in Massachusetts.

As a young man, Whitey Bulger had a troubled youth, engaging in criminal activities and spending time in various correctional institutions. He developed connections with other criminals during this time, laying the groundwork for his future involvement in organized crime.

Criminal Career: In the 1950s, Bulger became associated with the Winter Hill Gang, a criminal organization with ties to racketeering, loan sharking, drug trafficking, and other illicit activities. He quickly rose through the ranks, becoming a key figure in the Boston underworld.

Bulger was known for his ruthless tactics and ability to avoid law enforcement. He cultivated relationships with corrupt FBI agents, most notably John Connolly, which allowed him to receive information about investigations and avoid prosecution.

FBI Collaboration: One of the most notorious aspects of Bulger's criminal career was his collaboration with the Federal Bureau of Investigation (FBI). Through his connections with corrupt agents, including John Connolly, Bulger provided the FBI with information about rival criminal organizations in exchange for protection. This collaboration allowed Bulger to operate with relative impunity for several years.

Fugitive Years: In 1994, facing imminent indictment on racketeering charges, Bulger went into hiding with his longtime companion Catherine Greig. For years, they evaded capture, and Bulger became one of the FBI's Ten Most Wanted Fugitives.

Arrest and Trial: In 2011, Bulger and Greig were apprehended in Santa Monica, California, after a tip from the public. Bulger was extradited to Boston to face charges, including involvement in 11 murders. His trial began in 2013.

Conviction and Imprisonment: In 2013, Whitey Bulger was found guilty of multiple charges, including racketeering, money laundering, and involvement in 11 murders. He was sentenced to two consecutive life terms plus five years in prison.

Death: Whitey Bulger was transferred to the United States Penitentiary, Hazelton, in West Virginia. On October 30, 2018, he was found dead in his prison cell shortly after being transferred. The circumstances surrounding his death led to investigations and raised questions about prison security.

Whitey Bulger's life and criminal activities have been the subject of numerous books, documentaries, and films, contributing to his status as one of the most infamous figures in American organized crime history.

James (Whitey) Bulger's Alleged Victims - Multimedia Feature -

Dick Lehr

Early Life and Education: Dick Lehr was born on March 1, 1951. Details about his early life, including his place of birth and upbringing, are not widely available. Lehr has maintained a private personal life, and his focus has primarily been on his professional career.

Journalistic Career: Dick Lehr has had a distinguished career in journalism, working for several prominent publications. He was a reporter at The Boston Globe for over 25 years, where he covered a range of topics, including education, politics, and crime.

Lehr is particularly known for his investigative reporting and has been recognized for his contributions to journalism. His reporting often delves into complex issues, including criminal cases and legal matters.

Authorship: In addition to his work in journalism, Dick Lehr is an accomplished author. He has co-authored several true crime books, often collaborating with fellow journalist Gerard O'Neill. One of their notable works is "Black Mass: Whitey Bulger, the FBI, and a Devil's Deal," which explores the criminal career of James "Whitey" Bulger and his relationship with the FBI.

Teaching Career: Dick Lehr has also been involved in education. He has served as a professor at Boston University's College of Communication, where he shared his expertise with aspiring journalists.

Legacy: Dick Lehr's work, both as a journalist and an author, has left a lasting impact on the field of true crime reporting. His in-depth investigations and storytelling skills have contributed to a better understanding of complex criminal cases and legal issues.

Gerard O'Neill

Early Life and Education: Unfortunately, specific details about Gerard O'Neill's early life, including his date of birth and upbringing, are not widely available in public records. He has maintained a level of privacy regarding his personal life.

Journalistic Career: Gerard O'Neill has had a career as a journalist, specializing in investigative reporting and true crime. He has been associated with reputable publications and has contributed to in-depth coverage of criminal cases.

Authorship: O'Neill is known for co-authoring true crime books, often in collaboration with fellow journalist Dick Lehr. One of their notable works is "Black Mass: Whitey Bulger, the FBI, and a Devil's Deal," which delves into the criminal career of James "Whitey" Bulger and his connections with the FBI.

Collaboration with Dick Lehr: O'Neill's collaboration with Dick Lehr has resulted in critically acclaimed books that shed light on complex criminal cases and legal issues. Their joint efforts have been praised for their investigative depth and storytelling.

Legacy: While specific biographical information about Gerard O'Neill may be limited, his contributions to the field of true crime reporting and investigative journalism, particularly through collaboration with Dick Lehr, have left a lasting impact. The duo's work has been recognized for its ability to unravel and present intricate narratives surrounding criminal activities.


Black Mass

The Departed


The Blacklist

Ray Donovan

Whitey: United States of America vs. James J. Bulger


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