Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell

Wyatt Redd - July 6, 2018

In July 1943, the US Army was preparing to invade the island of Sicily. Since entering the war on the side of the Allies, the US had been fighting its way across North Africa, pushing the Axis out and securing control over the coast. Sicily would be the next step, giving the Allies a springboard to seize control of Italy. Of course, the Axis suspected that an invasion was imminent somewhere in the Mediterranean, and the Germans had moved troops into Italy to respond to any attempt to force a landing. The invasion would be far from a cakewalk. Luckily for the Americans, they were about to get help from an unlikely source: Mobster Lucky Luciano.

Charles Luciano was born Salvatore Luciana in Sicily in 1897. His father was a miner who dreamed of one day emigrating to America. Reputedly, his father kept a calendar from a passenger ship company and a jar underneath his bed where he would stash away money in the hopes of saving enough to make the journey. When Luciano was nine, his father’s dream came true, and the family took a ship to New York. The family settled in the city among the growing Italian-American community. However, like many first-generation Italian immigrants at the time, Luciano was eventually swept up into organized crime.

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell
Allied troops in North Africa. Wikimedia Commons.

Luciano dropped out of school at a young age and started his own gang. Luciano’s gang was unusual among Italian organized crime groups in that it served as a protection racket for Jewish kids in the neighborhood. They came to Luciano for muscle when they were targeted by the other gangs in the area. The unusual arrangement came to benefit Luciano when he met Meyer Lansky, a Jewish gangster who himself had a number of innovative rackets. The two eventually grew very close and found their relationship mutually profitable. Luciano benefited from Lansky’s earnings and Lansky from Luciano’s muscle.

Like many gangsters, Luciano also benefited from prohibition and moved into bootlegging. Combined with his protection rackets, prostitution, and drug peddling, Luciano was soon pulling in millions of dollars a year. But by the 1920’s, the tensions within the Italian-American organized crime community were running high. The Mafia had become split between the young, first-generation gangsters, and the older, Italian-born members of the Mafia. Typically, the younger gangsters were more willing to work with non-Italians and move into new rackets. Meanwhile, the older “Mustache Petes,” as they came to be known, were more conservative.

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell
Little Italy around the turn of the century when Luciano arrived in New York.

Luciano was recruited into the old guard faction by mob leader Joe Masseria. But while Luciano was willing to gun people down on Masseria’s orders, he and his boss had profoundly different ideas about the future of the Mafia. When the tensions between the two factions boiled over into war, it was Luciano who eventually helped negotiate a peace. Of course, he did so by organizing a hit on his boss and making a deal with the leader of the other faction, Salvatore Maranzano. The arrangement made Luciano the second man in the Mafia after Salvatore Marazano. For Luciano, that really just meant that total control over the Mafia in New York was simply a bullet away.

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell
Lucky Luciano’s mugshot. Wikimedia Commons.

By 1931, Luciano was chafing under the Marazano’s leadership. The time had come to have him dealt with. Using his connections to Meyer Lansky, Luciano hired four Jewish gunmen to visit Marazano’s office and gun him down. With Marazano’s death, Luciano took control over the Mafia. But unlike earlier bosses, he took a more hands-off approach to management. He encouraged other mafia families to make decisions collectively and avoid war by resolving disputes by negotiation instead of violence. In many ways, Luciano’s leadership set the stage for the development of the modern Mafia.

Things were good for Luciano for a time. He was making huge amounts of illegal money, and in spite of all their efforts, the police couldn’t seem to do anything about it. His nickname, “Lucky,” is often said to have been a reference to the fact that he seemed to be able to avoid prison time no matter how many times he was charged with a crime. In fact, this is probably not the case. No one is sure where he got his nickname. It might actually just be derived from the American pronunciation of “Luciano.” But the story does demonstrate how easily he seemed to be able to avoid justice.

Unfortunately for Luciano, that changed in 1936 when Special Prosecutor Thomas Dewey organized a massive raid on Luciano’s brothels. By setting the bails of Luciano’s associates whom he arrested higher than they could pay, he convinced many to testify against their boss in exchange for release. With the evidence, the charges stuck, and Luciano was sentenced to more than 30 years in prison. He continued running his family from jail as he appealed the sentence. But after the appeal was finally denied by the Supreme Court, he stepped down. It seemed as though Luciano might die in prison.

But then the US joined WWII. And the government was suddenly willing to look at some “non-traditional” strategies if it meant victory. One of the things that concerned them the most was the idea that the Italians or Germans might try to sneak spies into New York City through the ports or that the labor unions on the dock might suddenly strike, bringing the operation of the ports to a halt. Knowing that the Mafia had long controlled the unions and the docks themselves, they began reaching out to known organized crime figures for help, including Luciano.

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell
The Normandie aflame in New York’s port. Wikimedia Commons.

Whether or not the idea was a good one or even really necessary is a matter of some dispute. But there are some reasons that it would have seemed so to the government at the time. In 1942, a French ship, the Normandie, was being refitted in New York to serve as a troop transport craft when it suddenly caught fire. Given the atmosphere, it was reported that the fire was the work of German spies. Although ironically, a Mafia boss later claimed to have organized it. The truth, of course, is that the fire was probably an accident. Still, it made important people nervous, and “Operation Underworld” was born.

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell
The Queen Mary pulling into New York Harbor during the war. Wikimedia Commons.

“Operation Underworld,” was a Naval Intelligence plan that called for operatives to make contact with Jewish and Italian organized crime figures and enlist their help in keeping the ports safe and productive. In New York, Joe Lanza, a member of the Genovese crime family was recruited and he, in turn, reached out to Luciano. Luciano agreed to help under the condition that he be released from prison early. This proved difficult; it required a long period of negotiation to work out a deal that both sides were satisfied with.

But once the deal was struck, Luciano put out word among his contacts that the Mafia would now take the lead in keeping the waterfront safe. Even from prison, his grip on the docks was powerful, as his family had infiltrated many of the unions of dockworkers and teamsters. Since the U.S. was at war with Italy, the Navy worried that there would be Mussolini sympathists among the Italian-American dockworkers. Luciano agreed that his men would keep an ear out for anyone voicing any pro-fascist opinions. Exactly what would have happened had they found any isn’t clear. Presumably, the Mafia would have handled it in typical fashion.

There’s no real evidence that the scheme had any effect in preventing sabotage attempts along the docks. In fact, there’s no conclusive evidence that the Germans or Italians made any serious effort to sabotage ships in New York’s ports. While there were undoubtedly Axis intelligence operatives in the US, and likely at least a few people on the docks who might have been secretly sympathetic to the Axis cause, it’s hard to say if the Mafia’s influence had any real impact in foiling their operations. Either way, there were no ships sabotaged in New York during the rest of the war.

With the Invasion of Sicily in 1943, Luciano’s efforts proved a bit more productive. He had contacts among the Sicilian Mafia, who even in 1943 had a lot of influence on the island. Mussolini had made serious and sometimes effective efforts to break the grip of organized crime on Sicily before the war. Now it backfired as many Sicilian Dons were eager to see his government overthrown. With Luciano’s help, they provided important intelligence to the Allies including maps, photographs, and many used their influence to ensure that the Allied troops met little opposition from the populace.

Mafia Boss Lucky Luciano Helped the US Invade Italy from a Prison Cell
The Invasion of Sicily underway. Wikimedia Commons.

While it’s probably an exaggeration to say that Luciano was instrumental in the success of the invasion, he certainly tried to help. And with the war winding down in 1945, he made an official appeal to the Governor of New York, at this point the same Thomas Dewey who helped put him away, for clemency. It was granted, and Luciano was deported to Sicily. He continued to run his rackets from Italy and spent the rest of his life in a series of tangles with the law. Luciano finally died of a heart attack in 1962. His body was returned to New York, where it rests today in the city he both preyed on and briefly tried to protect.


Where did we find this stuff? Here are our sources:

“Lucky Luciano”. The Editors of the Encyclopaedia Brittanica, Encyclopaedia Britannica Inc. March 2018.

“Review: Operation Underworld by Paddy Kelly”. Hilary White, The Independent. April 2010.

“Allied Invasion of Sicily”. Adrian Gilbert, Encyclopaedia Britannica Inc. March 2017.