You Will Shoot Your Eye Out

One of the most improbable alliances in World War II history was a covert partnership between the United States government and organized crime. Known as Operation Underworld, this clandestine initiative was born out of wartime desperation.

With America’s eastern seaboard vulnerable to Axis sabotage and German U-boats decimating Allied shipping, federal authorities turned to an unlikely source for help — mobsters like Charles “Lucky” Luciano and Meyer Lansky.

These figures, once hunted by law enforcement, were now enlisted to safeguard ports, suppress labor unrest, and gather intelligence. What began as a tactical response to immediate threats evolved into a strategic collaboration that extended across the Atlantic and played a subtle but vital role in the Allied victory.

Sabotage and the USS Lafayette

The turning point came on February 9, 1942, when the USS Lafayette (formerly the SS Normandie) caught fire and capsized in New York Harbor. The ship, a French luxury liner being converted into a troop transport, was lost in an incident officially blamed on a welding accident. However, the timing, just two months after Pearl Harbor, sparked widespread fears of Nazi sabotage, adding urgency to efforts to secure the waterfront.

The incident exposed glaring vulnerabilities in port security and intensified concerns about Axis agents operating within the U.S. At the same time, German U-boats prowled the Atlantic, sinking over 120 Allied merchant vessels in the first quarter of 1942 alone. The Office of Naval Intelligence (ONI), overwhelmed and lacking resources, realized that traditional law enforcement couldn’t secure the docks. The Mafia, with its deep control over unions and street-level networks, offered a solution.

Operation Underworld

Launched in the spring of 1942, Operation Underworld was a highly classified initiative jointly orchestrated by the ONI and the U.S. Attorney’s Office. The program was conceived in response to growing concerns over Axis sabotage, labor unrest, and rampant theft along the New York waterfront, a vital artery for American military logistics during World War II. Recognizing the limitations of conventional law enforcement in securing the docks, federal authorities turned to an unconventional solution: enlisting the cooperation of organized crime.

Operation Underworld was spearheaded by Commander Charles R. Haffenden, who led ONI’s New York office and was directly responsible for coordinating with Mafia contacts. Given ONI’s hierarchical structure, such a sensitive and unconventional operation would almost certainly have required approval or tacit support from senior leadership.

The operation sought to harness the influence of Italian-American and Jewish mobsters, whose control over longshoremen’s unions and intimate knowledge of port operations made them uniquely equipped to monitor and protect the waterfront. Among the key objectives were the prevention of sabotage through surveillance and deterrence of foreign agents, the suppression of labor strikes that could disrupt wartime shipping, the curtailment of black-market theft of military supplies, and the collection of intelligence on Axis sympathizers and pro-fascist groups operating in urban centers.

The New York Port of Embarkation (NYPOE) served as a critical hub for deploying U.S. troops and supplies to overseas theaters, making it a strategic asset vulnerable to sabotage and espionage. Though NYPOE was not the direct focus of Operation Underwood, its logistical lifelines depended heavily on the civilian docks and labor unions that Operation Underworld helped stabilize. By curbing labor unrest and deterring Axis-aligned saboteurs, the operation ensured uninterrupted military shipments through New York’s port system, indirectly safeguarding the NYPOE’s vital wartime mission.

In exchange for their assistance, mob leaders were offered leniency in ongoing prosecutions, protection from further legal action, and, in select cases, early release from prison. Though controversial, the arrangement proved effective in stabilizing the docks and securing one of the nation’s most critical wartime assets.

Meyer Lansky

Meyer Lansky, the cerebral architect of the Jewish mob, was instrumental in brokering the alliance between organized crime and the U.S. government during World War II. Renowned for his financial acumen and strategic foresight, Lansky operated more like a corporate executive than a street-level gangster.

His long-standing ties with Italian-American crime families, particularly with Lucky Luciano, positioned him as a trusted intermediary capable of uniting disparate factions of the underworld. Lansky was respected not only for his intellect, but also for his ability to maintain order and resolve disputes without violence.

When federal agents approached him, Lansky saw the opportunity not just as a patriotic duty, but as a calculated move to protect his interests and elevate his influence. He agreed to cooperate on the condition that Luciano be involved, recognizing that Luciano’s control over the docks was essential. Lansky then mobilized Jewish gangsters, many of whom harbored deep resentment toward fascism and its antisemitism, to monitor Nazi sympathizers in New York and New Jersey. These operatives used intimidation, infiltration, and surveillance to disrupt pro-fascist activities.

Beyond the waterfront, Lansky’s network infiltrated German-American Bund meetings and tracked Axis-aligned operatives, feeding intelligence to federal authorities and helping neutralize domestic threats during a critical period of the war.

Lucky Luciano

Charles “Lucky” Luciano, widely regarded as the architect of modern organized crime in America, was serving a 30- to 50-year sentence at Dannemora Prison (now part of Clinton Correctional Facility) when U.S. authorities approached him during World War II. Despite his imprisonment, Luciano maintained considerable influence over New York’s waterfront through trusted associates like Joseph “Socks” Lanza, who controlled the Fulton Fish Market and held sway over the United Seafood Workers union.

This network gave Luciano indirect command over longshoremen and port operations, critical assets during wartime.

With Meyer Lansky acting as intermediary, Luciano agreed to cooperate with the Office of Naval Intelligence in exchange for potential clemency.

He instructed his men to assist naval intelligence officers, secure the docks against sabotage, and monitor for Axis agents. Luciano’s influence over labor unions also enabled him to prevent strikes and ensure uninterrupted military shipments.

His wartime contributions were deemed so vital that in 1946, New York Governor Thomas Dewey, who had led the prosecution against him, commuted Luciano’s sentence.

Luciano was subsequently deported to Italy, a decision that sparked public controversy. While critics viewed it as rewarding a criminal, supporters argued that his cooperation had helped safeguard American infrastructure during a critical period of the war.

Other Underworld Allies

While Lucky Luciano and Meyer Lansky were the central architects of Operation Underworld, several other prominent figures in organized crime played supporting roles that proved vital to the operation’s success. These men, each wielding influence over key sectors of the waterfront and labor unions, helped enforce security, suppress unrest, and maintain the flow of wartime logistics.

Frank Costello, often called the “Prime Minister of the Underworld,” also contributed through his deep political ties. A trusted confidant of Lucky Luciano, Costello’s influence over Tammany Hall and New York’s municipal apparatus enabled quiet coordination between law enforcement and organized crime. His behind-the-scenes maneuvering helped legitimize the operation and shield it from public scrutiny.

After Luciano’s imprisonment in 1936, he continued to run his crime family from behind bars, initially through Vito Genovese, his acting boss. However, when Genovese fled to Naples in 1937 to escape a murder indictment, Luciano appointed Costello, his consigliere and political strategist, as acting boss.

This transition placed Costello in a pivotal position by the time Operation Underworld launched in 1942, allowing him to serve as a crucial intermediary between the Mafia and government officials, ensuring the operation’s success through his unique blend of criminal authority and political finesse.

Joseph “Socks” Lanza, a prominent figure in New York’s maritime commerce and a capo in the Luciano crime family (later known as the Genovese family), was among the key contributors to Operation Underworld. Operating out of the Fulton Fish Market, Lanza wielded considerable influence over the United Seafood Workers union, giving him strategic control over a critical segment of the waterfront.

Rather than relying solely on brute force, Lanza leveraged his position to enforce discipline, maintain order, and discreetly oversee port activities. His cooperation with Naval Intelligence helped deter sabotage attempts and ensured the smooth transit of military cargo through one of the nation’s busiest hubs, reinforcing America’s wartime logistics during a period of heightened vulnerability.

Together, they formed a shadow network of wartime enforcers, operating under the radar but with significant impact. Their contributions, though less publicized than those of Luciano and Lansky, were essential to the success of Operation Underworld and the broader effort to protect America’s wartime infrastructure.

Invasion of Sicily

The Mafia’s utility did not end at the water’s edge. During Operation Husky, the Allied invasion of Sicily in July 1943, U.S. military planners faced formidable obstacles: rugged terrain, entrenched fascist resistance, and a population wary of foreign troops. Here too, Lucky Luciano’s connections proved crucial.

Through intermediaries, Luciano facilitated contact with Sicilian Mafia leaders, notably Calogero Vizzini, a dominant figure in Villalba with deep local influence. These mobsters acted as informal guides, helping Allied forces navigate unfamiliar landscapes, identify fascist loyalists, and avoid ambushes.

They also provided intelligence on German troop movements and used their authority to persuade villagers to cooperate with the invaders.

After the initial military success, Mafia figures played a stabilizing role in the region’s governance. Some were appointed to municipal positions, leveraging their local clout to maintain order and assist in rebuilding efforts. Their involvement helped fill the power vacuum left by the collapse of fascist rule and eased the transition to Allied control.

While their participation sparked debate over the long-term consequences of empowering criminal elements, their wartime contributions were undeniably effective. The collaboration in Sicily underscored the strategic value of unconventional alliances in achieving military objectives during World War II.

A Fierce Debate

Operation Underworld remained classified for decades, its details obscured by layers of secrecy and denial. When historians and journalists finally uncovered the truth, the revelations sparked fierce debate. Critics argued that the alliance legitimized organized crime and empowered figures who would later dominate the postwar underworld.

Supporters countered that the collaboration was a pragmatic response to wartime exigencies. In a moment of national peril, the government had few options and the Mafia delivered results. The operation also highlighted the porous boundaries between legality and necessity in times of crisis.

Final Thoughts

Operation Underworld showcases the complexities of wartime decision-making. Faced with sabotage, espionage and logistical chaos, the U.S. government turned to men it had once prosecuted to protect its ports and support the war effort. Luciano and Lansky, symbols of criminal enterprise, became unlikely allies, demonstrating that in times of war, alliances are often forged by necessity. Their contributions, though shrouded in secrecy and controversy, helped secure American shores and pave the path to victory in Europe.