Killing the Mob

Have you ever wondered how the romanticized image of gangsters—from Al Capone’s swagger to Bonnie and Clyde’s doomed love—became part of America’s cultural identity? In Killing the Mob, Bill O’Reilly and Martin Dugard take readers deep into the bloody, power-driven history of organized crime in America, showing how a network of bank robbers, bootleggers, hit men, and mob bosses shaped the twentieth century. At its heart, the book argues that organized crime is not just a criminal phenomenon—it’s a mirror for America’s obsession with freedom, power, and rebellion against authority.

O’Reilly contends that the evolution of the Mob—from Depression-era bandits like John Dillinger and Bonnie and Clyde to global kingpins like Lucky Luciano and Sam Giancana—reflects a dark underside of American ambition. The nation’s fight against these figures, led by obsessive lawmen such as J. Edgar Hoover and Robert Kennedy, was as much about defining moral order as enforcing the law. Yet their war often blurred the line between justice and politics, exposing America’s willingness to glamorize violence even while condemning it.

From Bank Robbers to Syndicate Lords

The book opens in the chaos of the Great Depression, when economic despair turned some criminals into folk heroes. Figures like John Dillinger and Pretty Boy Floyd exploited public hatred for banks, while Hoover’s fledgling Bureau of Investigation (later the FBI) transferred that anger into a national campaign against “Public Enemies.” What begins as a war on individual bandits soon morphs into a complex struggle against organized syndicates—criminal families like those of Luciano and Genovese—who bring discipline and strategy to their corruption.

Politics and Power

O’Reilly traces how the fight against crime intertwined with America’s political evolution. Hoover’s obsession with fame and control created the myth of the feds as America’s moral saviors. Later, as the Kennedys rose to power, the political stage and the underworld collided. The book reveals shocking connections between Mafia bosses and politicians—including the Kennedys’ alleged reliance on Mob-backed favors during the 1960 election. The lesson is clear: in America, crime and politics have often danced together, each manipulating the other for survival.

The Mob Goes Global

Beyond the streets of New York and Chicago, Killing the Mob explores how organized crime expanded into international conspiracy. World War II’s alliances between the U.S. Navy and Sicilian gangsters, the CIA’s recruitment of mobsters to assassinate Fidel Castro, and the spread of narcotics through global networks show that the fight against crime was never confined to American soil. O’Reilly exposes how mafia leaders raided not only national institutions but also wartime morality—trading secrets with governments that once vowed to destroy them.

The Cultural Paradox

Finally, the book examines how Americans transformed these outlaws into icons. Films like The Godfather and real-life legends of gangsters shaped our view of rebellion, success, and power. O’Reilly reminds you that the allure of crime—its glamour and danger—never truly disappeared. The Mob’s story is the story of modern America: a nation that respects law, idolizes freedom, and yet remains fascinated by the men who break every rule to seize it. In tracing this paradox, the authors invite readers to consider how moral compromise, national ambition, and the hunger for notoriety turned the crime wars into one of the defining dramas of the American century.

Bill O’Reilly begins by plunging you into the 1930s, a time when the Great Depression fractured America’s spirit. Banks were foreclosing daily, unemployment was soaring, and public anger was explosive. In this climate, thieves like John Dillinger, Bonnie and Clyde, and Pretty Boy Floyd became legendary. They didn’t just steal money—they stole the public’s imagination.

The Myth of the Heroic Bandit

Dillinger’s charm and audacious jailbreaks turned him into a Robin Hood figure. Bonnie and Clyde’s tragic romance sold newspapers. Floyd was hailed as the “Sagebrush Robin Hood.” These gangsters were simultaneously vilified and worshipped. You can imagine how their fearless defiance appealed to people crushed by poverty—they were symbols of control in a world spinning out of control.

Hoover’s Crusade for Order

Enter J. Edgar Hoover. Appointed to head the Bureau of Investigation in 1924, Hoover saw public sympathy for criminals as a direct threat to national stability. He engineered America’s first publicity-driven law enforcement campaign, branding gangsters as “Public Enemy Number One.” Using high-speed cars, Thompson submachine guns, and press conferences, Hoover turned his agents—soon known as G-Men—into heroes of a new era. Hoover’s obsession with control set the template for future policing: morality, politics, and spectacle fused together.

The End of the Romantic Outlaw

The killings of Bonnie and Clyde in 1934 and Dillinger’s dramatic death outside the Biograph Theater marked a turning point. The public’s romance with rebellious criminals shifted to fascination with disciplined mobsters like Al Capone and Lucky Luciano. Hoover, now armed with expanded federal laws and media power, was no longer chasing small-time robbers—he was confronting a new breed of organized men who turned crime into business. This transformation set the stage for a half-century conflict between law enforcement’s ideals and organized crime’s empire-building reality.

If John Dillinger turned crime into legend, J. Edgar Hoover turned policing into empire. O’Reilly portrays Hoover as both visionary and tyrant—a man who built the FBI from a bureaucratic backwater into one of the most powerful institutions in America. But in doing so, Hoover blurred the line between justice, propaganda, and political theater.

The Bureau’s Transformation

Hoover established strict discipline, moral codes, and training programs for his agents. He expanded fingerprint databases and insisted on education in law and accounting. Yet the Bureau initially faced restrictions: agents couldn’t carry guns or make arrests. Hoover lobbied Congress to expand his authority, leveraging public fear of crime after events like the Kansas City Massacre. By 1934, federal agents were armed, empowered, and romanticized in popular culture—they became “Hoover’s soldiers.”

A Cult of Personality

Like powerful figures in other historical books (compare Robert Caro’s depiction of Lyndon Johnson), Hoover obsessively controlled his public image. He curated stories of his success, suppressed evidence of failure, and gathered compromising files on politicians. In one chilling episode, he displayed John Dillinger’s death mask outside his office—a trophy and warning in equal measure. Hoover’s war against the Mob becoming a war for attention shows how crime fighting, in his hands, became performance art.

Legacy of Fear and Control

By the 1950s, the FBI was America’s moral authority. But Hoover’s paranoia and desire to maintain dominance led him to misuse his power—surveilling civil rights leaders and avoiding direct confrontation with organized crime for fear of revealing his inner compromises. His legacy reminds you that power built on fear can’t tell truth from protection. The institution he created remains a cornerstone of American law, but the man behind its legend embodied both the necessity and danger of authority unleashed.

As the Depression’s regional gangs faded, the Mafia emerged as a disciplined empire. Originating in Sicily’s shadowy feudal culture and transplanted through immigration to U.S. cities, it became a global network. O’Reilly traces this movement from Mussolini’s crackdown to Lucky Luciano’s creation of a worldwide syndicate that redefined organized crime.

From Sicily to New York

Benito Mussolini’s purge of Sicilian mobsters in the 1920s forced hundreds to flee to America. Once in New York, they found opportunity in Prohibition. Luciano forged an alliance of Italian, Irish, and Jewish bosses—the National Crime Syndicate—that replaced chaotic gang wars with a streamlined corporate model. Murders were outsourced to “Murder, Incorporated,” ensuring systematic enforcement. This was organized crime’s modernization: efficiency met brutality.

A Wartime Alliance

During World War II, Luciano struck deals with U.S. Naval Intelligence to secure Sicilian cooperation against Mussolini’s fascists. Mafia leaders became unlikely war partners. Their help with Operation Husky—the Allied invasion of Sicily—cemented their control after the war, giving the Mafia legitimacy and influence across Europe and America.

A New Kind of Empire

The postwar era transformed local crime into global enterprise: Cuba’s casinos, heroin routes through France, and American unions became profit lines. Luciano and his successors built transnational cartels tied to government contracts and intelligence operations. Their reach symbolized a world in which profit trumped patriotism. O’Reilly uses this story to remind you that corruption expands not from chaos but from partnership between greed and power.

Few chapters are more shocking than the one revealing the tangled relationship between the Kennedy family and organized crime. O’Reilly paints this as America’s Faustian bargain: politicians courting the Mob’s help to achieve power, only to wage war against them once in office.

The Secret Deals

During the 1960 election, patriarch Joseph Kennedy, himself no stranger to underworld connections, allegedly reached out to mobsters like Sam Giancana and Johnny Roselli to secure union votes and campaign funds for John F. Kennedy. Figures like Frank Sinatra acted as intermediaries—linking presidential ambition with criminal muscle. Hoover’s files later revealed conversations confirming mob involvement in campaign support. This alliance would haunt the Kennedys forever.

RFK’s Moral Crusade

As attorney general, Robert Kennedy became the Mob’s fiercest enemy. He led hundreds of prosecutions and authored the phrase “the enemy within.” Determined to purge America of its criminal underclass, he targeted Hoffa’s Teamsters Union, Marcello in New Orleans, and Giancana in Chicago. It’s an irony that RFK attacked the very network his family had once exploited. His war exposed corruption but also provoked deadly retaliation, culminating in a chilling symmetry between his fight and his death.

Power, Hypocrisy, and Death

O’Reilly suggests that the overlap between the Kennedys and the Mob fed speculation surrounding JFK’s assassination. Whether or not organized crime orchestrated the murder (as some theories propose), the alliances of the 1960s revealed a political system inseparable from power-brokering and moral compromise. It’s a warning: when righteousness meets corruption, neither emerges unscarred. The Kennedys’ tragic fate encapsulates America’s dangerous romance with both idealism and control.

One of O’Reilly’s most captivating insights is how the Mafia penetrated Hollywood. This isn’t just a criminal subplot—it’s the cultural engine that turned gangsters into stars and stars into gangsters. From Bugsy Siegel’s Las Vegas dream to Sidney Korshak’s quiet domination of the movie industry, the book shows how entertainment became another arm of organized crime.

The Fixer Behind the Curtain

Sidney Korshak, the “man behind Hollywood,” is a central figure. Acting as liaison among mobsters, studios, and unions, Korshak blended business and intimidation. He made calls that changed careers: saving Sinatra’s role in From Here to Eternity or silencing dissent over Mafia depictions in The Godfather. His quiet manipulation established Hollywood as a controlled market—an illusion factory governed by real criminals.

Stars Entwined with the Mob

Actors like Frank Sinatra, Dean Martin, and even Desi Arnaz found themselves tangled in Mafia influence. Sinatra’s friendships with Sam Giancana and Peter Lawford tied entertainment to politics, while the Rat Pack turned criminal glamour into mainstream chic. O’Reilly argues that Hollywood didn’t just report gangster stories—it humanized them, feeding America’s appetite for rebellion.

Art Imitating Life

By the 1970s, films like The Godfather reflected—and transformed—the criminal mythos. Mobsters mimicked onscreen rituals, adopting phrases and mannerisms from the movies that glorified them. As O’Reilly notes, America fell in love with the villains it sought to destroy, proving that storytelling can turn even violence into nostalgia. The culture that criminality built still entertains you today whenever you watch a gangster saga and feel admiration instead of fear.

The finale of Killing the Mob delivers a sobering reflection: no empire, criminal or otherwise, lasts forever. By the 1980s, federal operations, especially the undercover work of agent Joseph Pistone (Donnie Brasco), shattered the Mafia’s code of silence. What remained was not the romantic power of the gangster but the bureaucratic machinery of crime—stripped of its myths and cornered by modern surveillance.

Inside the Mob’s Collapse

Pistone’s infiltration of the Bonanno family exemplified the courage needed to dismantle organized crime from within. His five years as “Donnie Brasco” led to hundreds of indictments and revealed how deeply Mafia families interlaced business, unions, and politics. The exposure of their methods, combined with innovations like the 1970 RICO Act, made criminal hierarchy itself illegal—a turning point that weakened the syndicates’ structure.

Legacy and Reinvention

Despite its decline, O’Reilly argues the Mob never truly vanished—it evolved. From international drug cartels to cybercrime and financial fraud, organized crime followed profit where technology led. The lesson for you is timeless: wherever greed finds organization, corruption finds opportunity.

A Cycle of Obsession

In the end, O’Reilly’s chronicle is not merely about killers and kingpins—it’s about America’s addiction to the idea of power without restraint. The same fascination that once made Dillinger a celebrity now fuels streaming-series antiheroes. As long as ambition outpaces morality, the Mob’s spirit lingers. The war against it, O’Reilly implies, is the war within each person—the perpetual battle between integrity and desire.