Introduction

In "Killing the Mob," Bill O'Reilly takes readers on a thrilling journey through the rise and fall of organized crime in America. Set against the backdrop of the Great Depression and spanning several decades, this book explores how notorious gangsters gained fame, fortune, and power, while also revealing the complex relationships between the mob, Hollywood, and law enforcement.

The story begins in the early 1930s, during the depths of the Great Depression. As people across the United States lose their jobs, homes, and hope, a new type of criminal emerges. Bank robbers and gangsters capture the public imagination, blurring the line between villain and hero. This era gives birth to some of the most infamous names in American criminal history, including Bonnie and Clyde, John Dillinger, and Lucky Luciano.

O'Reilly's narrative weaves together the tales of these notorious criminals with the efforts of law enforcement, particularly J. Edgar Hoover and his newly formed Bureau of Investigation (later to become the FBI), to bring them to justice. The book also delves into the Mafia's involvement in World War II, its control over Hollywood, and its eventual downfall.

The Rise of Depression-Era Gangsters

Bonnie and Clyde: America's Outlaw Sweethearts

The story of Bonnie Parker and Clyde Barrow is one of the most famous criminal romances in American history. Their tale begins in 1930 when Bonnie, an unemployed waitress, meets Clyde, an impoverished laborer. Despite their humble beginnings and physical limitations (both walked with a limp), they soon embark on a crime spree that captures the nation's attention.

Bonnie and Clyde's criminal activities include stealing cars, robbing gas stations, and holding up banks. Their exploits make them celebrities, with many Americans viewing them as rebellious heroes fighting against the cruel banks that were pushing people into poverty during the Great Depression.

However, their story has a dark side. By 1934, Bonnie and Clyde had killed 13 people during their crime spree. This brings them to the attention of J. Edgar Hoover, the head of the Bureau of Investigation. Hoover, a dedicated crime fighter who lived a solitary life with his elderly mother, makes it his mission to bring the couple to justice.

On May 23, 1934, Hoover's agents finally track down Bonnie and Clyde. In a violent confrontation, both are killed in a hail of bullets. The death of Clyde, followed by Bonnie's anguished screams, leaves a lasting impact on the agents involved, highlighting the human cost of their criminal lifestyle.

John Dillinger: The Escape Artist

As Hoover intensifies his efforts to combat crime, he introduces the concept of "Public Enemy Number One" – a label reserved for America's most wanted and dangerous criminal. The first to receive this dubious honor is John Dillinger, a charismatic bank robber and gangster.

Dillinger's story is one of daring escapes and cunning. In 1934, he breaks out of jail in Indiana and immediately returns to his criminal ways, stealing nearly $50,000 from a bank in South Dakota just days later. His ability to evade capture frustrates Hoover and his agents, exposing the limitations of the Bureau of Investigation.

One of the most embarrassing episodes for Hoover occurs when his agents track Dillinger to a vacation lodge in Wisconsin. In a comedy of errors, the agents – who are mostly accountants and lawyers rather than trained law enforcement officers – mistake three local hunters for Dillinger and his crew. The resulting shootout leaves one person dead and two critically injured, while Dillinger escapes into the woods.

This incident prompts Hoover to rethink his approach, realizing the need for more professional and experienced agents. Three months later, when Dillinger is spotted at a Chicago cinema, Hoover sends a team of sharp-shooting police officers to apprehend him. Despite Dillinger's attempts to alter his appearance through plastic surgery, the police identify and kill him, marking the end of America's first Public Enemy Number One.

The Mafia's Rise to Power

The Mafia and World War II

As World War II rages on, an unlikely alliance forms between the Allies and the Mafia. In 1942, as the Allies prepare to invade Sicily, they face a daunting challenge: 200,000 Fascist troops entrenched in the island's mountains. To overcome this obstacle, they turn to an unexpected source of help – the Mafia.

The relationship between the Mafia and Fascism in Italy had been contentious. In the 1920s, Benito Mussolini had vowed to drive the Mafia out of Sicily, where it had long held sway over the local economy and population. This crackdown led many Sicilian mafiosi to flee to the United States, particularly New York, where they continued their criminal activities under the guise of being refugees from Fascism.

The FBI, concerned about potential Nazi sabotage along New York's harbor after the attack on Pearl Harbor, attempts to gather intelligence from the longshoremen working on the docks. However, they encounter a wall of silence due to the Mafia's control over the harbor and the code of omertà (silence) enforced among the workers.

Left with no other option, the FBI reluctantly turns to Lucky Luciano, a powerful Sicilian-American mobster imprisoned at the time. They strike a deal: in exchange for his freedom, Luciano would use his Mafia connections to ensure the safety of the New York harbor and gather strategic information from the remaining Mafia in Sicily to aid the Allied invasion.

This collaboration between the Allies and the Mafia highlights the complex and often morally ambiguous decisions made during wartime. It also sets the stage for the Mafia's increased influence and power in post-war America.

The Havana Conference and the Drug Trade

As Prohibition ends in 1933, the Mafia loses a significant source of income from bootlegging. By 1946, they're looking for new ways to make money, and their attention turns to a more dangerous and addictive substance: heroin.

To decide on this new direction, the Mafia calls a board meeting in true business fashion. This gathering, known as the Havana Conference, brings together 20 of the most powerful Mafia bosses in America. These criminals, belonging to different "families" but united under the alliance known as Cosa Nostra (Italian for "our thing"), meet in Cuba to avoid the scrutiny of American law enforcement.

Lucky Luciano, now banned from returning to the United States after his release from prison, heads the conference from his base in Havana. Despite his reservations about entering the drug trade, fearing it would jeopardize his chances of returning to America, Luciano ultimately agrees to the majority's wish to begin drug-running operations.

This decision proves to be a turning point for both Luciano and the Mafia. Within months, the Federal Bureau of Narcotics notices a significant increase in drugs entering the US from Cuba and quickly identifies Luciano as the source. As a result, they pressure Cuba to deport Luciano to Italy, effectively ending his reign as a powerful American mob boss.

The Mafia's entry into the drug trade marks a new era of increased wealth and influence for the organization. However, it also brings heightened scrutiny from law enforcement and sets the stage for future conflicts with authorities.

The Mafia's Grip on America

J. Edgar Hoover and the Mafia

By the 1950s, the Mafia's wealth and influence have reached unprecedented levels, largely due to their involvement in the drug trade. However, J. Edgar Hoover, the head of the FBI, maintains a puzzling stance: he refuses to acknowledge the existence of organized crime in America.

Hoover's position becomes increasingly untenable in 1950 when Tennessee legislator Estes Kefauver leads a US Senate Committee investigating Mafia activities. The committee subpoenas hundreds of mobsters and their victims, bringing the shadowy world of organized crime into the public eye for the first time. The televised proceedings captivate the American public, who are fascinated by the stylish gangsters and their tales of wealth and violence.

Despite the overwhelming evidence presented during the Kefauver Committee hearings, Hoover stubbornly refuses to admit the Mafia's existence. This stance leads to speculation about Hoover's motives, with some of his own agents privately believing that he is being blackmailed by the Mafia.

Rumors circulate that the Mafia possesses compromising photographs of Hoover in a romantic relationship with his second-in-command at the FBI, Clyde Tolson. In the homophobic climate of the 1950s, the release of such photos would have been career-ending for both men. While the truth of these rumors remains unconfirmed, they highlight the complex and often murky relationships between law enforcement and organized crime during this period.

The Apalachin Meeting: A Turning Point

In 1957, while Hoover continues to deny the Mafia's existence, a dedicated small-town police officer named Edgar Dewitt Croswell makes a breakthrough that changes everything. Croswell, a sergeant in the quiet town of Apalachin, New York, has been keeping a close eye on Joseph Barbara, a suspected high-ranking Mafia boss living in a luxurious local mansion.

Through meticulous observation, Croswell notices unusual activity at Barbara's estate. Large orders of premium meat from Chicago and numerous hotel bookings for a specific date in November raise Croswell's suspicions. He correctly deduces that Barbara is hosting a gathering of America's most powerful gangsters.

On the day of the meeting, Croswell and his local police force set up roadblocks around Barbara's property. As news of the police presence spreads, panic ensues among the mob bosses. Many flee into the surrounding woods, their expensive suits torn and muddied in the process. In total, Croswell manages to detain 60 mafiosi, dealing a significant blow to the organization's secrecy and operations.

The news of the Apalachin raid makes headlines across the country, forcing Hoover to finally acknowledge the reality of organized crime in America. This event marks a turning point in the fight against the Mafia, as law enforcement can no longer ignore or deny its existence.

Croswell's success, achieved through dedication and old-fashioned police work, stands in stark contrast to the FBI's previous ineffectiveness in tackling organized crime. It demonstrates that even in the face of powerful and well-connected criminals, determined individuals can make a significant impact in the pursuit of justice.

The Mafia's Influence on Hollywood

The Mob's Financial Hold on the Film Industry

The relationship between the Mafia and Hollywood in the 1960s is a fascinating and often overlooked aspect of American cultural history. The mob's involvement in the film industry stems from a combination of opportunity and discrimination.

In the early 20th century, many of Hollywood's pioneering film producers came from Eastern European Jewish backgrounds. While they possessed the talent and ambition to make movies, they often lacked the necessary capital. Traditional banks, influenced by prevailing prejudices, were reluctant to lend money to individuals from these ethnic backgrounds.

Faced with limited options, these producers turned to the Mafia for financing. The mob, always on the lookout for new revenue streams, saw the film industry as a golden opportunity to launder money and skim profits from successful productions.

The Mafia's influence extended beyond mere financing. They also gained control over various labor unions within the movie industry, including those representing screenwriters, construction workers, and electricians. This control gave the mob significant leverage over film studios. If a studio displeased the Mafia, they could simply instruct the unions to halt work on productions, effectively bringing the filmmaking process to a standstill.

The Case of Desi Arnaz and "The Untouchables"

A prime example of the Mafia's influence on Hollywood content is the case of Desi Arnaz and the TV show "The Untouchables." In 1957, Arnaz, famous for his role in "I Love Lucy," was producing this new cop show. However, the Mafia took issue with the show's portrayal of Italian Americans as criminals and "spaghetti-eating buffoons."

To address their concerns, the mob suggested that Arnaz cast an Italian American actor of their choosing in a heroic role. To emphasize the seriousness of their request, they intimidated the show's sponsors and even discussed the possibility of murdering Arnaz.

Faced with these threats, Arnaz quickly acquiesced to the Mafia's demands, agreeing to their casting suggestion. This incident illustrates the extent of the mob's power in shaping the content and representation in Hollywood productions during this era.

The Mafia's involvement in Hollywood had far-reaching consequences. It influenced not only the financial aspects of filmmaking but also the content and messaging of the productions themselves. This control allowed the mob to shape public perception, often softening or glamorizing their image in popular culture.

The Beginning of the End for the Mob

Law Enforcement Steps Up

As the 1960s progress, law enforcement agencies begin to take a more aggressive stance against organized crime. The embarrassment of the Apalachin raid and increasing public awareness of the Mafia's influence push the FBI and other agencies to intensify their efforts.

One key development is the increased use of wiretapping and electronic surveillance. These tools allow law enforcement to gather crucial evidence about the Mafia's operations and hierarchy. Additionally, the passage of new laws, such as the Racketeer Influenced and Corrupt Organizations (RICO) Act in 1970, provides prosecutors with powerful tools to target entire criminal organizations rather than just individual members.

The Valachi Hearings

A significant blow to the Mafia's code of silence comes in 1963 when Joseph Valachi, a member of the Genovese crime family, becomes the first made man to publicly acknowledge the existence of the Mafia. Valachi's testimony before a Senate committee provides unprecedented insights into the structure and operations of Cosa Nostra.

Valachi's revelations include details about the Mafia's initiation rituals, its organizational structure, and the names of high-ranking members. This testimony not only captivates the public but also provides law enforcement with valuable intelligence to pursue further investigations and prosecutions.

The Decline of Mafia Power

As law enforcement pressure intensifies and public perception shifts, the Mafia's grip on various industries begins to weaken. The increasing scrutiny makes it more difficult for the mob to operate with impunity, and many of their traditional revenue streams, such as protection rackets and labor union control, become less profitable and more risky.

Additionally, changing social and economic conditions contribute to the Mafia's decline. The children of many mobsters, benefiting from the wealth and opportunities their parents' criminal activities provided, choose to pursue legitimate careers rather than follow in their fathers' footsteps. This generational shift further weakens the Mafia's ability to recruit new members and maintain its power structure.

Final Thoughts: The Legacy of the Mob in American Culture

"Killing the Mob" provides a comprehensive look at the rise and fall of organized crime in America, highlighting how deeply the Mafia was entrenched in various aspects of American life throughout much of the 20th century. From its roots in the Great Depression to its peak in the post-war years and eventual decline, the story of the mob is inextricably linked with the broader narrative of American history.

The book illustrates how the lines between criminality and heroism often blurred in the public imagination, particularly during times of economic hardship. Figures like Bonnie and Clyde and John Dillinger became folk heroes to many, despite their violent crimes, because they were seen as striking back against a system that had failed ordinary people.

O'Reilly's narrative also sheds light on the complex relationships between organized crime, law enforcement, and government agencies. The collaboration between the Mafia and the Allies during World War II demonstrates how even sworn enemies can find common ground in extraordinary circumstances. Similarly, the long-standing rumors about J. Edgar Hoover's reluctance to acknowledge the Mafia's existence highlight the potential for corruption and compromise even at the highest levels of law enforcement.

The Mafia's influence on Hollywood is particularly fascinating, showing how organized crime shaped not just the financial aspects of the film industry but also the content of the movies and TV shows produced. This influence had a lasting impact on popular culture, often glamorizing or mythologizing the mob in ways that continue to resonate today.

Ultimately, "Killing the Mob" tells a story of power, greed, and the American Dream gone awry. It shows how a group of criminals were able to build an empire that touched nearly every aspect of American life, from the docks of New York to the glitz of Hollywood. At the same time, it chronicles the efforts of dedicated law enforcement officers, from small-town cops like Edgar Dewitt Croswell to federal agents, who worked tirelessly to bring these criminals to justice.

The book serves as a reminder of a turbulent period in American history, when organized crime wielded enormous power and influence. It also highlights the resilience of American institutions and the rule of law, which eventually prevailed against the mob's reign of terror and corruption.

As we reflect on this era, we can see echoes of its impact in contemporary issues surrounding organized crime, law enforcement, and the balance between security and civil liberties. The story of the mob in America is not just a tale of criminals and cops, but a complex narrative that intertwines with the nation's economic, social, and cultural development.

In the end, "Killing the Mob" offers a compelling look at a dark chapter in American history, one that continues to fascinate and intrigue us to this day. It reminds us of the ongoing struggle against organized crime and corruption, and the importance of vigilance in protecting the principles of justice and the rule of law.

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