Killing the Mob - Book Summary

Discover the dark allure of organized crime

During the turmoil of the 1930s — marked deeply by the Great Depression — America found itself grappling with unprecedented economic and social challenges. Jobs were scarce, families were destitute, and disillusionment was rampant. In these desperate times, traditional villains and heroes took on new faces. Banks, once pillars of stability, were now seen as heartless giants, while outlaws robbing these institutions began to capture the public's empathy and imagination.

This period heralded a new chapter in the narrative of American crime, where figures like Bonnie and Clyde weren't just outlaws; they were rebels with a cause, at least in the eyes of the beleaguered public. Beyond these bank-robbing icons, a deeper, more organized form of villainy was taking root — the rise of the Mafia and its sophisticated hierarchy of power.

In this intriguing dive into America's criminal underworld, you will explore how notorious gangsters not only pursued wealth and influence but also captivated society's attention — sometimes even its affection. We'll uncover:

— the unexpected alliance between the Allies and the Mafia during World War II,

— the mob's stealthy grip over the glitzy world of Hollywood, and

— the story of a relentless police officer who strategized to bring down the Mafia's elusive top echelons.

Join us as we step into a world where the line between right and wrong blurs, and discover how organized crime has woven its dark threads through the fabric of American history.

The tragic romance of America's legendary bandits

Amid the backdrop of economic despair during the Great Depression, a new kind of American folklore was born, starring none other than the infamous duo, Bonnie and Clyde. These notorious figures weren't just criminals; they were symbols of rebellion against an oppressive economic system, captivating the nation with their audacious exploits.

Enter J. Edgar Hoover, the zealous head of the Bureau of Investigation, the precursor to today's FBI. Tasked with capturing these high-profile outlaws, Hoover's first target was the pair known across the country for their daring bank robberies and glamorous, albeit illicit, adventures.

Bonnie Parker and Clyde Barrow's tale began in 1930 in the throes of hardship. Bonnie, an out-of-work waitress, and Clyde, a struggling laborer, found solace and a shared purpose in each other's company, evolving swiftly from down-on-their-luck individuals to partners in crime. Their criminal activities ranged from auto theft to armed robberies, marking their transition from the impoverished to the infamous.

Despite their criminal facade, Bonnie and Clyde were not the menacing figures one might imagine. Both physically impaired — Bonnie from a severe car accident and Clyde from a self-mutilation incident aimed at avoiding prison labor — they relied on each other in a profound expression of their bond; Clyde often carried Bonnie when her injuries proved too painful.

Their humanity shone through in the personal photos they took, which, once discovered and published, transformed them from mere criminals into romantic figures, symbols of resistance. With Bonnie often posing with a menacing sawn-off shotgun, the couple was sensationalized as glamorous rebels, challenging the institutions that many felt had failed them.

Yet, the darker aspects of their journey were undeniable. Throughout their notorious spree, Bonnie and Clyde were responsible for the deaths of 13 individuals. Hoover, who was a stark contrast to the adventurous couple with a sparse personal life, focused intently on halting their crime wave. His commitment to law enforcement was personal and relentless.

On the fateful day of May 23, 1934, Hoover's agents caught up with Bonnie and Clyde, leading to a tragic yet dramatic end near Gibsland, Louisiana. The gunfire barrage that halted their stolen Ford V8 was as fierce as their storied love affair. Clyde was struck first, leaving Bonnie to realize their fate alone, her anguished screams echoing in the memories of those who witnessed their demise.

Thus concluded the saga of Bonnie and Clyde, the couple who lived by the gun — and ultimately, died by it — but not without leaving behind a legacy enveloped in romance, rebellion, and the harsh realities of their tumultuous era.

The rise and fall of John Dillinger, America's first public enemy number one

In the treacherous landscape of 1930s America, J. Edgar Hoover decided to up the ante in the fight against crime by introducing a novel and alarming label: public enemy number one. This title was destined for the most dangerous and sought-after criminal active at the time, and it would remain assigned until the bearer was either captured or dead.

John Dillinger, a bank robber and charismatic outlaw, was the first to be branded with this ominous title. Dillinger, with his affable demeanor, might have passed as just another amiable bar-goer, yet beneath this facade was a man whose criminal mastery was so renowned that it inspired a Hollywood movie — tragically, the last film he would ever watch.

In 1934, following a daring escape from an Indiana jail, Dillinger swiftly orchestrated a bank heist in South Dakota, absconding with almost fifty thousand dollars. The heist set the stage for a relentless manhunt led by Hoover's Bureau of Investigation. On April 22, FBI agents traced Dillinger to a remote vacation lodge in Wisconsin. As Dillinger and his associates unwound inside with a casual game of cards, agents concealed themselves in the surrounding snowy landscape, poised to strike.

However, the operation was doomed to falter. Adjacent to Dillinger's hideout was a diner frequented by local hunters. That fateful evening, a misunderstanding ensued when FBI agents mistook three departing hunters for Dillinger and his gang. The subsequent shootout led to tragic misfires: one hunter dead, two severely injured, and Dillinger vanished into the night woods.

The mishap underscored a critical flaw in Hoover’s strategy. Despite his intention to cleanse the Bureau of pervasive corruption by hiring professionals from outside the policing world, the inexperienced white-collar workers — largely accountants and lawyers rather than seasoned officers — were ill-equipped for the gritty realities of field operations.

Undeterred by the setback, Hoover revised his tactics. Learning that Dillinger was attending a film in Chicago, he dispatched a team of adept sharpshooters to apprehend him. Disguised by recent plastic surgery, Dillinger was no less identifiable to the trained eyes of law enforcement. Minutes after the movie concluded, as the audience spilled into the night, the life of America's archetypal public enemy was abruptly brought to a close.

John Dilligan's legacy as a daring gangster ended that night, but his story continues to captivate as a stark illustration of crime and consequence in the heat of America's most desperate days.

Unlikely allies: How the Mafia joined forces with the Allies during World War II

In the critical year of 1942 — with World War II raging — the Allies plotted their invasion of Sicily, a strategic island stronghold brimming with over 200,000 Fascist troops. Faced with such formidable defense nestled in the rugged terrain, the Allies found an unexpected source of assistance: the Mafia.

The backdrop to this surprising alliance began in the 1920s under the rule of Benito Mussolini. Determined to eradicate the Mafia's powerful and oppressive hold over Sicily, Mussolini launched a severe crackdown on the organization. This campaign forced many mafiosi to flee — many of whom found refuge in the United States, particularly New York, under the guise of escaping Fascism. Once in America, these Sicilian mobsters seamlessly transitioned back into their criminal enterprises, quickly entrenching themselves in bootlegging, violence, and extortion.

However, the outbreak of World War II brought a unique set of challenges and opportunities. Following the infamous attack on Pearl Harbor in 1941, concerns over potential acts of sabotage within the United – particularly in vital locations like New York's harbor – reached a fever pitch. The problem for J. Edgar Hoover and his FBI was that the Mafia had a stronghold over the Longshoremen working the docks, enforced by a strict code of silence known as "omertà." This made it virtually impossible for FBI agents to extract any useful information directly.

Left with limited options, the FBI approached the most influential Sicilian American mobster, Lucky Luciano, who was then serving time in prison. In a move driven by sheer necessity, an agreement was forged between the U.S. government and the Mafia leader. In exchange for Luciano's cooperation — using his expansive Mafia network to secure the harbor against sabotage and gather crucial intelligence from the Sicilian Mafia — he would earn his freedom.

This pact turned the tides in favor of the Allies. Luciano’s contacts in Sicily were instrumental in providing the Allies with the local knowledge and support needed to facilitate their invasion. The cooperation between the Mafia and the Allies, though born out of desperate circumstances, highlights a poignant chapter in wartime strategy, where the quest for victory necessitated alliances with even the most unlikely of partners. Through this alliance, the Allies and the Mafia worked together to challenge a common foe: the oppressive regime of Fascism in Europe.

From prohibition profits to narcotics downfall: The downfall of Lucky Luciano

The Prohibition era was a golden age for the mob, as they thrived on the illegal import and distribution of alcohol across the United States. However, the repeal of Prohibition in 1933 abruptly halted their lucrative trade, pushing the Mafia to seek new avenues for profit. By 1946, their focus had shifted to a much more dangerous substance: heroin.

Recognizing the need for a strategic shift, the Mafia treated their criminal activities with the seriousness of corporate business, convening a major "board meeting" to decide their next steps. This wasn't just any meeting; it was a gathering of 20 of the most influential Mafia bosses across America, all part of the formidable alliance known as Cosa Nostra — Italian for "our thing."

To dodge the prying eyes of American law enforcement, these crime lords convened in Havana, Cuba, under the protection of a corrupt government that was all too willing to ignore their presence in exchange for substantial bribes. This location also served as the base for Lucky Luciano, who had been banned from the U.S. following his release from prison. Operating from Havana allowed Luciano to stay as close as possible to his underworld empire.

Despite the overwhelming consensus among the mob bosses to dive into the narcotics trade, Luciano harbored reservations. As the senior leader, he predicted that any blowback from this illicit business would fall squarely on his shoulders, potentially sabotaging any chance of negotiating his return to the United States — a return he deeply desired.

Nonetheless, bowing to the majority’s sentiment and realism over idealism, Luciano hesitantly agreed to initiate the Mafia's entry into drug trafficking. This decision would prove disastrous for him personally. Within months, the Federal Bureau of Narcotics detected a significant surge in drugs flowing into the U.S. from Cuba and traced the operation back to Luciano.

The consequences were swift and severe: the U.S. authorities demanded that Cuba deport Luciano back to Italy, effectively severing him from direct control over his American criminal activities. This marked the inexorable decline of Luciano’s reign as a potent figure in American organized crime, illustrating how a pivot to drug trafficking ultimately led to his professional ruin.

The decade of denial: Hoover, the Mafia, and the swirl of 1950s intrigue

Throughout the 1950s, as the Mafia's fortunes soared through illicit drug trafficking, the specter of organized crime loomed large over America. Yet, paradoxically, FBI Director J. Edgar Hoover staunchly denied the existence of such an organized entity. To Hoover, the concept of a cohesive network of Italian American mobsters was a myth; crime, in his eyes, was the work of individual crooks operating independently.

Despite Hoover's denials, public awareness and concern about the Mafia were about to surge. In 1950, the spotlight turned sharply on organized crime thanks to Tennessee Senator Estes Kefauver, who chaired a groundbreaking Senate Committee dedicated to investigating the Mafia. Kefauver's fierce determination led to subpoenas for hundreds of mobsters and their victims, compelling them to share chilling accounts of the Mafia's operations.

As these testimonies unfolded, they were broadcast on national television, gripping the nation. Viewers were simultaneously fascinated and horrified by the mafia's extravagant lifestyle and brutal exploits. The dramatic exposure was not intended to last beyond a year, but the overwhelming public reaction — fueled by thousands of letters to the Senate pleading for extended investigations — pushed the committee's activities into 1952.

Despite the glaring evidence and public fascination, Hoover maintained his stance, continuing to deny the existence of the Mafia. This obstinate refusal led to whispered suspicions among even his federal agents. Some speculated that Hoover's denial was not born of ignorance but of coercion; he was purportedly being blackmailed by the very organization he denied.

Rumors circulated that the Mafia had compromising material on Hoover's private life, specifically alleging a romantic relationship with his close associate, Clyde Tolson. In an era marked by rampant homophobia, such revelations could have devastated their careers. The pair were inseparable, often seen dining together nightly and vacationing together, further fueling speculations.

This tangled web of denial, blackmail, and hidden personal lives set the stage for a critical juncture. Something significant was on the horizon that would challenge Hoover's capacity to ignore the growing power of the Mafia, ultimately testing his control over the narrative and his own legacy within the FBI.

A humble officer and a historic crackdown on mob bosses

In the late 1950s, while FBI Director J. Edgar Hoover continued to dismiss the existence of organized crime syndicates, a dedicated police sergeant from upstate New-Zork was making moves that would soon thrust the Mafia into the national spotlight. Edgar Dewitt Croswell, a sergeant in the quiet town of Apalachin, lived and breathed law enforcement. Stationed at the local police barracks night after night, Sergeant Croswell was deeply familiar with the criminal underworld in his jurisdiction. Among the individuals on his radar was Joseph Barbara, a known Mafia boss who resided in a palatial estate locally.

Croswell's breakthrough came after he noticed suspicious preparations at Barbara's mansion—large meat orders from a Chicago butcher and several luxury hotel bookings for November 14. Piecing together these clues, Croswell surmised that a major event was planned, likely a high-level Mafia meeting.

Barbara's mansion indeed served as the venue for a significant gathering on that day — a meeting not seen since the infamous Mafia summit in Havana in 1946. The country's most powerful mob bosses convened at the luxurious villa, there to strategize about expanding their criminal empire further into legitimate industries such as textiles and sugar, and even deeper into the justice system, discussing plans for taking their operations global.

As these mob leaders plotted their future moves, Sergeant Croswell and his team set up a strategic roadblock around the estate. The first to stumble upon this police barricade was a delivery boy, who quickly informed the mob bosses of the police presence. Despite their notorious reputality for ruthlessness, the trapped mobsters panicked at the prospect of arrest and long prison terms. In a chaotic scramble, many fled into the surrounding woods, their expensive suits tearing against branches as they sought to escape.

By the end of that fateful night, Croswell had successfully apprehended around 60 Mafia members. The arrests made national headlines the following morning, catching even J. Edgar Hoover off-guard as he choked on his breakfast reading the news. This event marked a turning point; Hoover could no longer ignore the blatant reality of organized Mafia activity in America.

Thanks to the tenacity of an ordinary police officer who refused to turn a blind play to the ominous undertows in his town, the myth of the non-existent Mafia was conclusively dispelled, redirecting the course of America's battle against organized crime.

The shadowy alliance between the Mafia and 1960s Hollywood

The glitz and glamour of Hollywood in the 1960s often eclipse a darker liaison that played out behind the scenes—one involving the influential hands of the Mafia. While the limelight shone brightly on stars like Marilyn Monroe and Kirk Douglas, another type of power was maneuvering the strings of the movie industry, rooted deeply in organized crime.

The reason the Mafia became so intertwined with Hollywood goes back further than the cinema lights themselves, intertwined with an American social issue: racial discrimination. During Hollywood's formative years, many of the emerging film producers came from Eastern-European Jewish backgrounds. Despite their undeniable talent and vision, these producers often faced financial roadblocks, primarily due to prevailing prejudices among traditional banking institutions.

Left with limited options, these pioneering filmmakers turned to the Mafia for the capital needed to bring their cinematic dreams to life. The mob, ever-opportunistic, saw a lucrative chance not only to invest in a burgeoning industry but also to skim hefty profits from the movies they helped finance.

Beyond financial maneuvers, the Mafia exerted control over various Hollywood labor unions, from screenwriters and construction workers to electricians. This control meant that if a film studio crossed the mob, retribution could be swift and severe, often involving strikes and work stoppages instigated through union influence.

One stark example of the Mafia's grip on Hollywood content came with the production of the television show "The Untouchables." Produced by Desi Arnaz in 1957, the show quickly drew the ire of the Mafia for its unfavorable portrayal of Italian Americans as criminals. The mob's discontent was not taken lightly—they exerted pressure on Arnaz to cast an Italian American in a heroic role, a suggestion strongly enforced through intimidation tactics on the show’s sponsors and even murmurings of potential violence against Arnaz himself.

Faced with such menacing influence, Arnaz capitulated, casting an actor favored by the mob, thereby directly shaping the show's direction under the looming threat of organized crime.

This symbiotic and often sinister relationship between the Mafia and Hollywood during the 1960s serves as a reminder that the stories unfolding on screen were sometimes scripted by the unseen, powerful hands of the mob, dictating narratives in more ways than one might imagine.

A century under the shadow of organized crime

The encapsulation of these narratives reveals a startling truth about the 20th century: organized crime wove itself into the very fabric of American culture. The influence of gangsters was not confined to shadowy alleys or hidden speakeasies; it reached the highest levels of government, the glamorous studios of Hollywood, and even the homes of ordinary citizens.

Throughout the decades, from the Prohibition era to the flashy 1960s, Americans found themselves both fascinated and appalled by the mob’s formidable presence. Whether it was the audacity of notorious figures like Bonnie and Clyde, the strategic manipulations of Lucky Luciano, or the Mafia's unlikely role in American military strategies during World War II, the saga of organized crime in America is as complex as it is compelling.

In essence, the story of organized crime throughout the 20th century is a stark reminder of the mob’s pervasive reach and its lasting impact on American society — illustrating that the allure and danger of the gangster underworld became as quintessentially American as apple pie.