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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.

About the Authors: Dick Lehr & Gerard O'Neill

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.

Other Writings:

Dick Lehr

Black Mass

Whitey

White Hot Hate

The Fence

Trell

Dead Reckoning 

The Birth of a Nation

Judgement Ride

The Underboss

The Birth of a Movement

Gerard O'Neill

The Underboss

Rogues & Redeemers

 

Dick Lehr on Writing

Synopsis

This is a true story of violence, double-cross, and brutal murders involving Irish mobsters and corrupt FBI agents in South Boston. Two boys - John Connolly, and James Whitey Bulger - grew up together on the streets of South Boston. Decades later, in the late 1970s, they would meet again. By then, Connolly was a major figure in the FBI's Boston office and Whitey had become godfather of the Irish Mob. What happened between them - a dirty deal to trade secrets and take down Boston's Italian Mafia in the process - would spiral out of control, leading to murders, and drug dealing, and racketeering indictments. And, ultimately, to Bulger making the FBI's Ten Most Wanted List. Told in narrative style by the Boston Globe reporters who covered the case from the beginning, Black Mass is an epic crime story that is also a book about Boston and Irish America; about the pull of place; and about the ties between people - ties that bind, and ties that blind.

Discussion Questions

  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.

Fact vs Fiction: James 'Whitey' Bulger

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.

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.

TV & Movies

Black Mass

While his brother Bill (Benedict Cumberbatch) remains a powerful leader in the Massachusetts Senate, Irish hoodlum James "Whitey" Bulger (Johnny Depp) continues to pursue a life of crime in 1970s Boston. Approached by FBI agent John Connolly (Joel Edgerton), the lawman convinces Whitey to help the agency fight the Italian mob. As their unholy alliance spirals out of control, Bulger increases his power and evades capture to become one of the most dangerous gangsters in U.S. history.

The Departed

South Boston cop Billy Costigan (Leonardo DiCaprio) goes under cover to infiltrate the organization of gangland chief Frank Costello (Jack Nicholson). As Billy gains the mobster's trust, a career criminal named Colin Sullivan (Matt Damon) infiltrates the police department and reports on its activities to his syndicate bosses. When both organizations learn they have a mole in their midst, Billy and Colin must figure out each other's identities to save their own lives.

Brotherhood

The Caffee brothers live in an Irish-American neighborhood in Providence, R.I., known as "the Hill." Tommy Caffee is a family man whose ambition and street smarts help him navigate the world of Providence politics, protecting the Hill at all costs. Unfortunately, his gangster brother Mike returns to town, hoping to take over the city's underworld activities. Complicating matters further are Tommy and Mike's proud mother Rose, Tommy's wife Eileen, gang boss Freddie Cork and local detective Declan Giggs.

The Blacklist

For decades, ex-government agent Raymond "Red" Reddington has been one of the globe's most wanted fugitives. But then he agreed to work with the FBI to catch his "blacklist" of mobsters, spies and international terrorists -- on the condition that he must work with profiler Elizabeth Keen. Red's true intentions -- choosing Liz, a woman with whom he seemingly has no connection -- are unclear. Does Liz have secrets of her own? Red promises to teach Liz to think like a criminal "to see the bigger picture," whether she wants to or not.

Ray Donovan

Ray Donovan is a "fixer" for Hollywood's elite. He is the go-to guy that the city's celebrities, athletes and business moguls call to make their problems disappear. It's a much more lucrative job than his previous work as a ruthless South Boston thug, vaulting him within reach of the truly wealthy and powerful. But no amount of money or the expensive things it can buy can completely mask Ray's past, a past that continues to haunt him with troubled brothers always calling and his father's recent release from 20 years spent in prison. Now a free man, Ray's father, Mickey, arrives in Los Angeles to get what he feels is rightfully his. Mickey's desire to reconnect and settle old scores with his family -- including Ray's wife and kids, who have never met the family's patriarch and are anxious to get to know him -- threatens to destroy everything Ray has built for himself.

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

Filmmaker Joe Berlinger examines the story of South Boston crime boss Whitey Bulger, including his sensational trial. Key players on every side reveal Bulger's influence on crime and law enforcement.

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

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