“In view of the friendly feeling towards America entertained by a great number of citizens of Italy,” President Franklin Roosevelt wrote in a telegram to British Prime Minister Winston Churchill, “and in consideration of the large number of citizens of the United States who are of Italian descent, it is my opinion that our military problem will be made less difficult by giving to the Allied Military Government [in Sicily] as much of an American character as is practicable.”
Churchill agreed with Roosevelt’s sentiments, and Roosevelt was right. Residents of Sicily were as vehemently opposed to Fascism and Fascist dictator Benito Mussolini as most Americans were by 1943. All the Allies really needed to do was convince the Sicilians they were all on the same side before landing there.
To do that, they needed an insider, someone with connections on the island and a high enough profile to ensure that officials in Sicily were all on the same page. Unfortunately for the U.S. government, the ideal candidate was sitting in a cell in New York’s Great Meadow Correctional Facility for pandering, masterminding New York City’s prostitution rings. Whether he was guilty or not, the government knew that Charles “Lucky” Luciano was the head of a major organized crime syndicate in the city (the Mafia’s existence, at the time, was still unconfirmed).
The United States also knew that Luciano still held sway with his organization, whether they knew how deep his involvement from prison was. They had already struck a deal with Luciano in 1942 to use his organization to protect the docks in New York from saboteurs and strikes. The anti-Mussolini Luciano was happy to oblige. As he was still running the gang from his cell using Vito Genovese as an acting boss, it was no problem.
By 1943, the United States and its Allies were on the offensive in World War II. Their next stop after the successful invasion of North Africa was Italy via the island of Sicily: Operation Husky. 160,000 troop from all Allied nations, 600 tanks, 14,000 vehicles and an untold number of ships and aircraft were gathering to deal the Axis their first blow on their home turf. They wanted to make sure everything went according to plan.
But setting a man like Luciano free to use him in the active war effort was something else entirely. When approached for the idea, Luciano suggested either parachuting him onto Sicily or allowing him to get there himself via a neutral country, like Portugal. American officials were split on the idea. Some were all in favor of winning by any means necessary, others questioned the post-war public reaction when they found out the U.S. Navy sent the head of American organized crime to the war zone.
Luciano, again, was only too happy to help with the latest developments. He suggested American troops land at Golfo di Castellammare, which was a favorite drug smuggling port for the gangs (they did not). Ultimately, Luciano was not freed for the war effort. Instead, he connected the Navy to some trusted mafia contacts with insider information about the island. Luciano would give them names and his associate Meyer Lansky would bring those ment o the Office of Naval Intelligence for a debriefing. The mob boss also put American agents in touch with Sicilian connections on the island. The Sicilian resistance would aid the Allied landings before and during Operation Husky.
It turned out that the Sicilian Mafia was also eager to help the Americans. Mussolini’s regime had hit the mafia pretty hard in the decades before World War II, jailing, torturing, and forcing many into exile. Though there is no official evidence for mafia support during the actual landings, the Americans swept through Sicily in little more than a month, while British forces were frequently fought to a standstill. No one really knows for sure if the mafia convinced the Italians to give token resistance to the American forces.
For his assistance, the United States and the State of New York commuted Lucky Luciano’s sentence and he was deported to Italy. There he would try to keep a hold on his family back in the United States.