1. September 17, 1954 – Charles “Lucky” Luciano

In 1954, William B. Herlands was an investigator that wanted answers. The most notorious crime boss in the history of the United States, the man who created La Cosa Nostra, Charles “Lucky” Luciano, was freed from prison for his “war services” and living as a freeman in Italy. Herlands wrote a classified letter to the governor of New York, Thomas E. Dewey:

Lucky Luciano, Operation Underworld, Operation Husky
The Vintage News

“Pursuant to your direction an investigation has been made of all the facts and circumstances relating to the commutation of the sentence of Charles Luciano and the granting of parole for purpose of his deportation. I have the honor to transmit herewith the report of that investigation.” Now that the letter and full investigation has been declassified, what follows is the incredible story of what he found.

2. December 7, 1941 – Dannemora “Little Siberia” Prison

When the United States was plunged into WWII, Lucky Luciano was very much on the sidelines at Clinton Correctional Institute in Dannemora, New York (nicknamed “Little Siberia” for how remote it was). He’d been in for five years of potentially fifty years for running a prostitution ring.

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Luciano didn’t have any delusions about his situation, so he did what he could to make himself more comfortable. He had a personal chef and spent his time directing the building of the best prison church in the country. He also ran the business of his “family” from prison, and the United States government needed his help.

3. February 9, 1942 – German spies

On the afternoon of February 9, 1942, a large passenger ship in New York Harbor was being converted to ferry U.S. troops across the Atlantic Ocean. The large, fast, and powerful SS Lafayette was a perfect fit for the mission, as the United States had entered WWII barely two months prior.

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Sean Munger

A fire down below alerted the fire department, and within fifteen minutes they were on the scene. They fought the blaze for over five hours and managed to put it out, but sadly the water from their hoses caused the SS Lafayette to sink. Onlookers gathered at Pier 88 and looked on in horror, as suspicions spread that the ship was blown up by German spies.

4. February 10, 1942

Luciano learned about the attack on the SS Lafayette from a newspaper in prison. Initially, his criminal brain made him think it was an insurance scam, but at a time when the Japanese attack on Pearl Harbor was still very fresh in everyone’s minds, the sinking of the SS Lafayette was terrifying.

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It was feared that German agents had infiltrated New York Harbor and were not only blowing up ships but feeding information to German U-boat commanders in the Atlantic. The government didn’t want the public to know, but the Germans managed to sink 171 ships off the east coast of the U.S. in early 1942. The U.S. government needed solutions, and outside-the-box thinking.

5. February 11, 1942

“If the Chief of Police makes a deal with the leading gangsters and the deal results in no more hold ups, that Chief of Police will be called a great man – but if the gangsters do not live up to their word the Chief of police will go to jail.” – Franklin Delano Roosevelt, September 1938

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Naval History Heritage Command

The home front had to be secured if the U.S. was going to have any chance of bringing the fight to the enemy, and that task fell to the Navy. Captain Roscoe MacFall, chief intelligence officer of the Third Naval District, was a 40-year veteran, and even though he was up to the task, his first action fell far short of genius.

6. March 7, 1942

Captain MacFall was under immense pressure when he took on the challenge of securing one of the largest harbors in the United States, and the loss of the $5 million Lafayette that could’ve escorted 10,000 troops was very much on his mind.

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Libcom.org

MacFall ordered his men to get down to the docks and figure out what was going on. Suddenly, naval officers in dress uniforms descended on New York Harbor and started asking questions. They were met with as much cooperation as a toddler receiving a flu shot, but they did find out who was calling the shots around the docks.

7. March 8, 1942

MacFall was on the right path, but he needed someone with a little more style and creativity to be successful. He was receiving tremendous pressure from the top and needed results fast. In May 1942, a U-boat landed two groups of German saboteurs in New York and Florida, with enough explosives to blow up half the Eastern Seaboard.

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Smithsonian Magazine

But one of them flipped and turned his coconspirators in just before they blew up the Hell’s Gate Bridge in New York. It was lucky. In fact, it was extremely lucky, and MacFall was sure there were more German agents out there.

8. March 25, 1942

MacFall found his man in the “swashbuckling” Commander Charles Radcliffe Haffenden. Haffenden didn’t waste any time and contacted investigators and the New York district attorney. He wanted to set a meeting with the man who ran the docks, Joseph “Socks” Lanza, who also happened to be a part of the Luciano crime family.

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Haffenden made the trek to the Harbor and met Socks at his headquarters. Socks has been described as a “bulldozer,” and was a hulking 250-pound gangster who got his nickname by “socking” anyone who disagreed with him. From his headquarters in the bar above the Fulton Fish Market, Socks and Haffenden ironed out the details of Operation Underworld.

9. March 26, 1942

Socks Lanza jumped at the opportunity to help the Navy, as the mafia in the United States had a bone to pick with the government in Italy. Since the fascist Benito Mussolini took control of Italy, he brought everything in the country under his thumb, including organized crime.

Lucky Luciano, Operation Underworld, Operation Husky, Fulton Fish Market
History Network

This meant that a lot of Luciano and Socks’ friends back in Italy had been killed. Socks was happy to help the Navy, but Commander Haffenden was slightly reticent about empowering the mafia, so he had Socks’ office wiretapped. Haffenden wasn’t satisfied, as there were still plenty of docks that were beyond his reach. He asked Socks if there was someone capable of “snapping the whip in the entire underworld.”

10. April 15, 1942

Socks had solid control over his own territory, but not the Irish mafia–controlled docks on the West Side. Not only that, but the Brooklyn docks were controlled by the notorious Albert Anastasia, who was known as the “High Lord Executioner.”

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Cosa Nostra News

Haffenden wanted Socks to get Anastasia on board, but Socks wanted nothing to do with him. When Haffenden pressed, Socks came up with the man who pretty much invented organized crime and had made his reputation by his ability to work with rival gangs. His name was Lucky Luciano, and when he was presented with the idea of helping the U.S. government, he had no interest in doing so.

11. April 30, 1942

At the time Socks was helping out the government, he was actually under indictment. He didn’t want to reach too far in his efforts, and just as the Navy didn’t fully trust him, he certainly didn’t fully trust the government. He needed help, and in April 1942, Socks reached out to “Agent X” and told him he required assistance.

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NY Daily News

According to Herlands’ report, “Agent X” told Commander Haffenden about this problem, and Haffenden responded by saying, “already working on it.” Luciano didn’t know it at the time, but Haffenden got Luciano out of “Little Siberia,” and had him transferred to a prison closer to the action.

12. May 12, 1942

“Luciano’s transfer to the Great Meadow Prison on May 12, 1942, was designed to make him more accessible and therefore more effective in his war-aid activities,” says the Herlands report. Socks and Haffenden had everything in place, but they also knew Lucky would need convincing.

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In the early 1930s, Luciano had rival mafia leaders executed, then he reorganized the New York underworld into five families. His longtime partner along the way was the Jewish-born Meyer Lansky, whom the Navy recruited to go have a talk with Luciano. It’s safe to say that at this point, the Navy and the Italian-American mafia were in bed together.

13. May 15, 1942

According to the Herlands report, Lucky had idea why he had been transferred. He must’ve thought he caught a break, because being out of “Little Siberia” caused him to cede power over his family to a liaison, and he rarely received visitors if at all.

Lucky Luciano, Operation Underworld, Operation Husky
Den of Geek

So when a mafia lawyer and his old friend Meyer Lansky showed up on May 15th, Lucky reportedly said, “What the hell are you fellows doing here?” Lansky told Lucky about the Navy, and the fact that Socks had given them his name. Lucky agreed to help the government and insisted on having a chat with Socks.

14. June 4, 1942

Luciano did have some reservations about helping the government. He insisted on total secrecy and cited the fact that he had a deportation order to Italy. That meant the U.S. government could deport him to Italy any time they wanted, and if news of his involvement in Operation Underworld got out, he feared he could be “lynched there.”

Lucky Luciano, Operation Underworld, Operation Husky
Messy Nessy Chic

Not only that, but if the other four families in New York found out about Lucky’s cooperation, they might try to have him killed, thinking he was spilling secrets. But with secrecy assured, and the likes of trusted confidants like Lansky and Socks, Lucky got to work saving the United States from the Nazi menace.

15. June 5, 1942

Socks hit the scene with great energy when Lucky gave him permission to “use his name.” The first person he contacted was the de facto head of the Luciano crime family, Frank Costello. Costello was on board immediately, and the two went about forming an unshakable alliance of the worst mobsters out there.

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NY Daily News

Brutal Albert Anastasia’s acceptance into the alliance assured New York Harbor was going to be watched over carefully. With the further addition of Longshoremen’s Union enforcer Johnny “Cockeye” Dunn (who would later die in the electric chair), the United States had a formidable weapon against the Nazis.

16. June 6, 1942

“It was expected that the mere appearance of these men on the piers would serve as a deterrent,” testified a longshoreman some years later. “[It was] a warning to cooperate with the United States war effort or face the consequences.”

Lucky Luciano, Operation Underworld, Operation Husky
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The mafia had managed to do for the Navy in just a couple days what they’d been trying to do for seven months. Now that the mafia was set up in New York Harbor, Haffenden laid out the strategy to Socks, who relayed the information to Lucky, who decided the best way to solve problems, and finally Socks and Haffenden would administer the decision. They got to work immediately.

17. Spring 1942

Oddly enough, during WWII, the Navy’s first line of defense in the Atlantic Ocean was commercial fishermen (that should illustrate how ill prepared the United States was when it entered WWII). The Navy had worked out a complex coding system that would enable fishermen to radio in if they spotted a German U-boat.

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ThoughtCo

The fear was that if German agents successfully infiltrated the crew of fishermen, then there could be catastrophic results. They also feared that ex-rum runners from the Prohibition era might be persuaded to help for a price, by providing fuel, supplies, and intelligence. Not to mention sabotage on the docks, which was still fresh on everyone’s minds.

18. Summer 1942

Haffenden wanted agents posted on the long-range fishing boats that were being used as the first line of defense. He presented the problem to Socks, who spoke with Lucky, and days later Socks was able to get Navy agents, under the protection of the mafia, to report on strange activity on the fishing boats.

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Staten Island North Shore

Socks laid it out in true like a true wise guy when he told Haffenden, “You let me know when you want the contacts made, or what you want, and I’ll carry on.” So Socks opened up his books, and allowed Haffenden to have a look. That’s when the Navy man got a little drunk with power.

19. Summer 1942

Haffenden needed a place to run Operation Underworld, and in true mafia fashion the Navy commander secured a room at the Astor Hotel Suites. For months, the most notorious mobsters in the country, such as Frank Costello, Albert Anastasia, and Bugsy Siegel, moved freely in and out of his office.

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NYC Architecture

The coalition of mobsters was highly successful in locating possible conspirators, and nearly overnight the threat disappeared. But mobsters being mobsters, their methods of handling potential spies were less than wholesome. Many cases were reported that involved beatings and broken bones, and one notorious case involved the killing of two men.

20. Summer 1942

Johnny “Cockeye” Dunn was eventually executed for murder, and his role in running a murder-for-hire business. In the summer of 1942, there was an alleged incident when Commander Haffenden asked Cockeye to investigate two men he believed were German agents. They were never heard from again.

Lucky Luciano, Operation Underworld, Operation Husky, Johnny "Cockeye" Dunn
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A wiretap on Haffenden’s phone picked up the conversation about the incident, and it was reported that Cockeye said, “They’ll never bother us again.” Say what you will about the methods, and this certainly doesn’t excuse it, but “not a single act of sabotage, labor strike, or suspicious fire occurred for the rest of the war.”

21. January 1943

Lucky Luciano’s grip on his power began to strengthen with his new location, and his star-studded list of gangster visitors. The Navy certainly made the right call in employing the mafia for the job of securing New York Harbor, because even though Project Underworld was in place the entirety of the war, the mafia was incredibly effective.

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In Roosevelt History

But the government wasn’t done with the mafia, and as it was, Lucky Luciano wasn’t done with the government. This time both President Roosevelt and Prime Minister Winston Churchill of England needed his help. Orders came down from the top, and Operation Husky was started.

22. January 14, 1943

When President Roosevelt and Prime Minister Churchill met at Casablanca in January 1943, they agreed that after wrapping up their invasion of North Africa, the next target would be the Italian island of Sicily. Churchill called it “the soft underbelly” of the Axis hold on Europe, but the Allies possessed surprisingly little intelligence about the bottom of the Italian boot.

Lucky Luciano, Operation Underworld, Operation Husky, President Franklin D. Roosevelt, Prime Minister Winston Churchill, Casablanca
Forward With Roosevelt

Navy Intelligence identified their Italian partners as possibly being able to help, and Haffenden was approached to run the operation. That’s when Haffenden formed the F-Target Section, which was tasked with gathering intelligence to aid the Allied invasion of Sicily.

23. January 29, 1943

On January 29, 1943, Operation Underworld and Operation Husky suffered a blow, as Socks Lanza was found guilty on six counts of extortion. He was sentenced to at least seven years in prison, effectively ending his involvement in WWII. Evidently the Navy didn’t have enough sway to get him off, and Haffenden was livid.

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But by now, Lucky wasn’t getting his information just from Socks, as his visitor list included notorious criminals such as Bugsy Siegel and Frank Costello, meaning his influence in New York was growing. In Socks’ place, Haffenden assigned Lucky’s most trusted confidant, Meyer Lansky, to step in.

24. February 1943

Contrary to popular belief, most intelligence work of this sort is not conducted by spies or agents, but by collecting information from citizens themselves. Haffenden met with Lansky, who relayed to Lucky that they were looking for people who either lived, or still lived, in Sicily that would be sympathetic to the Allied cause.

Lucky Luciano, Operation Underworld, Operation Husky, General George S. Patton, Field Marshall Bernard Montgomery, Sicily
Liberation Trilogy

The British and Americans lacked even basic information, so they were looking for people who had drawings, postcards, and especially maps. It was obvious to Lucky that the Navy had a long way to go, but Lucky was very happy to help rid his native Italy of the fascist dictator who might have him lynched if given the chance.

25. March 1943

Lucky was definitely the right man for the job. He set up a narcotics operation in the old country a long time ago, and simply used his contacts in Sicily to help. He loved the idea, and the people he asked to help were happy to assist.

Lucky Luciano, Operation Underworld, Operation Husky, Vincenzo "The Executioner" Mangano
Mafia Genealogy

Lucky and Lansky came up with a couple of names that would help them in their quest. One of those people was Joe Adonis, who was indicted for just about everything the United States has a law against, but never saw prison time. They also recruited the don with the most Sicilian ties: Vincenzo Mangano, aka head of the Gambino crime family, aka “The Executioner.”

26. April 1943

While “The Executioner” got to work on contacts in Sicily, Joe Adonis went to work in New York. He nabbed every Italian-American  he could find that once lived in Italy, even kidnapping the former mayor of one Sicilian town. Adonis was extremely effective at his job, but his secret weapon was Lucky himself.

Lucky Luciano, Operation Underworld, Operation Husky, Joe Adonis
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“Sometimes some of the Sicilians were very nervous,” Lansky later testified. “Joe would just mention the name of Lucky Luciano and say he had given them orders to talk. If the Sicilians were still reluctant, Joe would stop smiling and say, ‘Lucky will not be pleased to hear that you have not been helpful.’”

27. May 15, 1943

By mid-May 1943, Lucky and company had produced a trove of information to aid in the invasion, and provided the U.S. government with several names of possible sympathizers in Italy. Several two-man commando teams armed with Lucky’s information boarded a plane bound for Europe.

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World War 2 Headquarters

Also in mid-May, the Allies were able to fully secure North Africa, which freed up forces for the invasion of Sicily. They rushed their preparation for invasion and were ready to go by July. When Patton’s army landed, he had several of the two-man teams embedded in his unit, and one particular group used Luciano’s contacts to conduct a highly important mission.

28. July 9, 1943

Several decades earlier, an Italian-American killed a police officer, and Lucky successfully smuggled him out of the country and into Italy. Lucky gave American agents the man’s name, and when they found him, he led them right to the Italian Naval Command headquarters.

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Magnum Photos

The agent said that Lucky’s named worked “like a magic wand” in Sicily. All of the sudden, a mixed unit of Navy operatives and Italian wise guys armed with pistols and shotguns were raiding the Command Headquarters together. The mafia provided cover fire while the agents penetrated the building. A trove of intelligence was gained from this mission when the agents cracked their safe and stole the document inside.

29. February 10, 1946

The Allied invasion of Sicily, while not without difficulty, was an extremely successful operation that resulted in its collapse by August 17, 1943. Thanks to key intelligence provided by Lucky and the Italian mafia, the Allied landing went smoothly, and victory was achieved.

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Famous Biographies

Operation Underworld and Operation Husky were virtually over after the Sicily invasion, and WWII would be over almost two long years later. The day after Germany capitulated, Lucky Luciano filed a request with the government to be released from prison on contingency he be deported to Italy. On February 10, 1946, Lucky left the United States for the final time as he boarded a ship to Italy.

30. October 9, 1977

In 1954, at the time of the Herlands investigation, Thomas E. Dewey, the prosecutor who convicted Luciano, allowed the Navy access to him when he became governor. When the investigation commenced, Herlands felt that Dewey had some explaining to do.

Herlands report, Thomas E. Dewey
Aeon

But the governor held fast and also lobbied against the Herlands report being released to the public. In 1977, the Freedom of Information Act allowed the report to be declassified, and the American public gasped at the scope of the operations. As for Luciano, he tried to set up shop in Cuba, but was sent back to Italy. He died in 1961 a free man, and allegedly ran his illegal operations from Naples until his dying day.