Operation Underworld: How an Italian Mafia Boss in Prison Helped the US Invade Sicily in World War II

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1931 New York Police Department mugshot of Luciano. (Wikimedia Commons)

A luxury ocean liner burned and capsized in New York Harbor on Feb. 9, 1942. The SS Normandie, being converted into a troopship, caught fire during welding work and took 6,000 tons of water from firefighting efforts before rolling onto its side in the Hudson River. One worker died and more than 1,500 people evacuated the vessel.

The Navy immediately suspected sabotage. German U-boats had sunk 120 American merchant ships in the first three months after Pearl Harbor, and fears of Axis agents operating along the waterfront ran high. Naval Intelligence started looking into local dock workers. Italian and German workers controlled by organized crime networks remained silent when federal investigators asked them questions.

Commander Charles Haffenden of the Office of Naval Intelligence needed help investigating the incident and protecting the waterfront. He turned to the one man who could make dock workers talk, Charles Lucky Luciano, who was serving 30 to 50 years in New York's Dannemora Prison for running prostitution rackets.

Mugshot of Italian Mafia gangster Charles Luciano in 1936. (Wikimedia Commons)

From Prisoner to War Asset

Thomas Dewey, the special prosecutor who sent Luciano to prison in 1936, had called him the most dangerous gangster in America. By 1942, Luciano controlled New York's Five Families crime syndicate from behind bars. Meyer Lansky, a Jewish mobster and Luciano's longtime associate, served as his connection to the outside world.

The Navy approached Luciano through his attorney, Moses Polakoff, in March 1942. Intelligence officers offered better prison conditions in exchange for Luciano's help securing the docks. Luciano agreed. The Navy moved him from Dannemora to Great Meadow Prison in May 1942, closer to New York City and easier for his associates to visit.

Luciano ordered his criminal network to watch for saboteurs, report suspicious activity and prevent labor strikes that could disrupt the war effort. Joseph Socks Lanza, who controlled the Fulton Fish Market and United Seafood Workers Union, became a key contact. 

Lanza told Haffenden during their first meeting: "You let me know where you want the contacts made, or what you want, and I'll carry on."

Albert Anastasia, who ran the Brooklyn docks and Murder Inc., guaranteed cooperation from the longshoremen.

Dock strikes stopped after Luciano became involved. No major acts of sabotage occurred in New York Harbor for the rest of the war. Lieutenant Maurice Kelly, a former New York Police Department officer who joined Naval Intelligence after Pearl Harbor, testified years later in the Herlands investigation about the success of Luciano's connections.

"From the time Commander Haffenden made these contacts with Luciano there was a very open and cooperative condition that existed between the investigators and the people that were very influential on the various docks in the Port of New York," Kelly said.

The Navy's covert partnership with organized crime, codenamed Operation Underworld, achieved its immediate goal of securing the docks.

Suspicion about Mafia sabotage in the fire and sinking of Normandie (renamed Lafayette for war service), led to Operation Underworld. (Wikimedia Commons)

The Sicilian Connection

Planning for Operation Husky, the Allied invasion of Sicily, began at the Casablanca Conference in January 1943. President Franklin Roosevelt and British Prime Minister Winston Churchill agreed Sicily would be the first step toward defeating Italy and opening a southern front in Europe.

The Navy encountered a major problem. American intelligence on Sicily remained limited. There were serious gaps in knowledge about Italian and German defenses on the island. Local customs, beaches, tides, terrain and other features were also unknown. Traditional intelligence sources could not provide the detailed local information needed for a successful amphibious assault.

Haffenden formed the F-Target Section to gather intelligence on Sicily. He turned again to Luciano, who maintained extensive connections to the Sicilian Mafia despite 20 years in America. Luciano provided names of Sicilian contacts in the U.S. who could be trusted. Meyer Lansky brought these contacts to Naval Intelligence for debriefings.

Sicilian immigrants living in New York provided maps, photographs of coastlines and harbor layouts. Some offered corrections to existing naval charts. The information came from fishermen, merchants and former residents who knew Sicily's terrain, ports and villages from personal experiences.

Luciano also provided valuable names of local leaders and Mafia connections on the island that American forces could turn to once the troops stormed ashore.

Historians debate the actual value of this intelligence. Some credit Luciano with providing crucial information that saved American lives. Others argue the intelligence amounted to picture postcards and basic geography that trained military planners already possessed.

Map of Sicily in the White House Map Room. August 1943. (Wikimedia Commons)

Why the Mafia Wanted Mussolini Gone

The Sicilian Mafia had reasons to help defeat Italy's Fascist regime. Throughout the late 1800s, organized crime in Italy, especially Sicily, ran rampant. Mayors, police chiefs, lawyers and many influential residents were controlled by the Mafia, while average Sicilians were expected to pay taxes and protection fees to the criminals.

The rise of Fascism in the country would change that.

Benito Mussolini appointed Cesare Mori as Prefect of Palermo in 1925 with orders to eradicate organized crime and restore government control. Mori soon arrested more than 11,000 suspected Mafia members by 1928 and forced many to flee Sicily altogether, with many arriving in the U.S.

Future New York crime bosses Joseph Bonanno and Carlo Gambino escaped Fascist persecution by immigrating to America. The Sicilian Mafia's power structure was shattered, but still continued operating in the shadows. WWII brought even further economic hardship to the Sicilian people, diminishing what little profits and power the Mafia held.

Members of the Mafia on both sides of the Atlantic wanted revenge on Mussolini and saw the Allied invasion as their chance. The largest demographic to serve in the U.S. Army during the war were Italian-Americans, with many having experienced prejudices and hardship, they were eager to oust Mussolini and free their ancestral homeland. The Mafia was eager to help them do so.

President Roosevelt also understood the political value of Italian-American sentiment. He wrote to Churchill that giving the Allied military government in Sicily as much of an American character as possible would ease the invasion, given the large Italian-American influence across the nation and in the military who overwhelmingly opposed Fascism.

Cesare Mori in Sicily, wearing the infamous black shirt of the Italian MVSN. (Wikimedia Commons)

The Invasion and Its Aftermath

Operation Husky began July 10, 1943. More than 150,000 Allied troops landed on Sicily's southern coast in the largest amphibious assault of the war. Lieutenant General George Patton commanded the U.S. Seventh Army while British General Bernard Montgomery led the Eighth Army.

Italian coastal defenses melted away, German-Italian counterattacks were pushed back, British forces moved north to Messina as Patton blitzed west against staunch Italian defenses. Many Italian-American soldiers experienced their familial homeland for the first time or found themselves fighting on soil they had emigrated from years prior.

Stories emerged about Mafia support for the troops during the invasion. The most famous involved Don Calogero Vizzini, a Sicilian Mafia boss from Villalba. According to legend, American tanks displayed yellow scarves with a black L for Luciano to signal friendly forces. Vizzini allegedly rode on an American tank for six days, guiding troops through mountain passes and directing his men to eliminate Italian snipers.

Modern historians largely dismiss these tales as myths. Salvatore Lupo, a leading scholar on the Sicilian Mafia, stated the story about Mafia support for the invasion is just a legend without any foundation. Ezio Costanzo, who studied the topic extensively, found no evidence of significant Mafia contribution to Allied military success.

What historians do confirm is that the Allied Military Government of Occupied Territories appointed Mafia figures as mayors across Sicily after the invasion. Vizzini became mayor of Villalba and an honorary colonel in the U.S. Army. The Allies sought anti-Fascist local leaders to help restore local control on the island and support occupation troops.

This, however, mistakenly empowered organized crime figures who would dominate Sicilian politics for decades.

The Sicilian campaign ended on Aug. 17, 1943. Allied forces suffered approximately 24,850 casualties. The Italians suffered hundreds of thousands of casualties, the Germans lost tens of thousands, though many Axis troops escaped to mainland Italy. 

Nevertheless, the invasion led directly to Mussolini's overthrow on July 25, barely two weeks after the landings began. The first major Axis power unconditionally surrendered to Allied forces soon after.

Don Calò used to walk around in shirtsleeves and overalls. His slovenly dress and laconic speech were typical Mafia affectations. It was not done for a Mafia chieftain to show off in the matter of his clothing or any other way, and sometimes, as in Don Calò's case, this lack of concern for appearances was carried to extremes." – Norman Lewis. (Wikimedia Commons)

Luciano's Release and the Herlands Report

Luciano petitioned for clemency on May 8, 1945, the day Germany surrendered. His attorney cited invaluable service to the military, particularly regarding the invasion of Sicily. Governor Dewey, who as a prosecutor had put Luciano in prison, now weighed the commutation request.

On Jan. 3, 1946, Dewey commuted Luciano's sentence on condition of immediate deportation to Italy. Luciano had served nine and a half years of his 30-to-50-year sentence. Dewey's statement acknowledged Luciano's cooperation but was vague about its true value.

Upon entry of the United States into the war, Luciano's support was sought by the armed services in coercing others to provide information concerning any possible enemy attack, Dewey wrote. It appears that he cooperated in such effort, though the actual value of the information procured is not clear.

Luciano sailed to Italy on Feb. 9, 1946, never to return to America. Rumors spread that he had bribed his way out of prison. The Federal Bureau of Narcotics claimed Luciano ran drug smuggling operations from Italy and that his wartime service had been minimal.

Dewey ordered an investigation in 1954 to address the allegations. William Herlands, the state's commissioner of investigation, interviewed dozens of witnesses and reviewed classified records. His report, completed that year but kept secret until 1977, concluded that there can be no question about the value of this project.

The Herlands Report stated that Luciano had helped Naval Intelligence contact Sicilian immigrants who provided useful information about Sicily. His assistance directly benefitted and assisted the military in planning for, invading, and winning on Sicily.

One naval officer who worked with the Sicilian contacts testified that the intelligence gave Allied forces "an insight into the customs and morals of these people—particularly Sicilians—the political ideology and its mechanics on lower echelons, the manner in which the ports were operated, the chains of command together with their material culture, which enabled us to carry out the findings and purposes of our mission."

The report noted that after Luciano's involvement began, dock worker strikes ceased and no significant acts of sabotage occurred in New York Harbor after that point. Whether Luciano's influence directly caused these outcomes remains unclear, but authorities noted the possible correlation.

Luciano at the Excelsior Hotel in Rome, 1948. (Wikimedia Commons)

Assessing the Legacy

The extent of Mafia assistance to Operation Husky remains debated. Selwyn Raab, author of "Five Families," called Luciano's role in the Sicily invasion a total myth, arguing he lacked the Sicilian connections to make a meaningful difference and that his help amounted to postcards of ports.

Historian Tim Newark, who wrote extensively on Mafia involvement in World War II, took a more measured view. He acknowledged that Luciano's colleagues helped gather information about Sicily from New York's Italian community but concluded Luciano was of little practical use in Sicily itself despite persistent myths.

The truth likely falls between these viewpoints. Luciano facilitated contacts between Naval Intelligence and Sicilian immigrants. Whether this intelligence proved decisive or merely supplemented existing military planning remains debatable. The massive Allied military advantage in Operation Husky suggests the invasion would have succeeded regardless of Mafia assistance.

American soldiers overseeing the disarmament of Italian soldiers on Ustica during Operation Husky. (Wikimedia Commons)

Despite the continued debates, the U.S. government did partner with organized crime during World War II. The arrangement secured New York's waterfront, gathered some intelligence on Sicily, and resulted in the early release for one of America's most dangerous criminals. 

The partnership also strengthened the Mafia's position in postwar Sicily and Italy, consequences that would affect both nations for decades. In fact, the Italian Mafia continues as a powerful criminal element in southern Italy and Sicily today.

For Luciano, he was able to continue his criminal life in Italy for years after the war. As he was being deported from the U.S., he allegedly said, "I'm really glad to be getting out of this country. I will be a free son-of-a-bitch. I will be a free man in Italy, even though I do not intend to stay there long." 

Luciano died in Naples on Jan. 26, 1962. His body was permitted to return to New York for burial. Today, he is remembered as the father of organized crime in the U.S., the father of the Italian Mafia in New York, and is often recognized as the American gangster that helped the government take down Fascist Italy in WWII.

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