Infamous America - LUCKY LUCIANO Ep. 5 | "Operation: Underworld”

Episode Date: April 16, 2025

Luciano flees New York to evade Thomas E. Dewey. But after months of searching, Dewey’s agents find Luciano and bring him back to face charges related to a prostitution business. Luciano fears he will spend the rest of his life in prison, but then the U.S. government asks for his help to keep the New York ports safe during World War II. Luciano has an opportunity to earn his freedom, but it will come with a high price. Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join   Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial.   On YouTube, subscribe to INFAMOUS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage.   For more details, please visit www.blackbarrelmedia.com. Our social media pages are: @blackbarrelmedia on Facebook and Instagram, and @bbarrelmedia on Twitter. Learn more about your ad choices. Visit megaphone.fm/adchoices

At the end of 1931, Charles Luciano changed the American Mafia. Though he kept the five-family structure that Salvatore Maranzano instituted, Luciano went a step further in order to avoid unnecessary bloodshed. His most innovative idea was the creation of the commission, a board of directors consisting of seven mob bosses. For the first few years, Luciano's changes succeeded. Each mafia family carved out its own rackets, and disputes were quietly settled.

And even though the rest of the country was experiencing financial hardship because of the Great Depression, the mafia thrived. But the mafia soon faced a new enemy, a federal prosecutor in New York named Thomas Dewey. Dewey made it his mission to fight organized crime. In 1935, he went after legendary gangster Dutch Schultz. Schultz wanted to kill Dewey, but Luciano refused to allow it.

When Schultz decided to go through with the assassination anyway, Luciano gathered the bosses of the newly formed commission, and they voted to kill Dutch Schultz. At the end of October 1935, Schultz was murdered in a restaurant bathroom in Newark, New Jersey. With Schultz out of the way, Luciano hoped Thomas Dewey would turn his attention elsewhere. But Luciano was wrong.

Dewey focused on Luciano, and he used the Luciano crime family's control of prostitution to target the most powerful boss in the mafia. By March 1936, Dewey was ready to make his move against Luciano. Luciano had a decision to make, either take out Dewey or do something else. Luciano decided his best option was to skip town. Before Dewey's agents could put Luciano in handcuffs,

Luciano fled New York. He headed to Middle America, to a town called Hot Springs, Arkansas. By the mid-1930s, Hot Springs had become an infamous mob town. Gangsters from all across the country established illegal casinos there, and some even retired in Hot Springs.

Hot Springs most famous resident at the time was an Irish gangster named Onie Madden. Madden had been one of the most powerful bootleggers in New York during Provin. When Prohibition ended, Madden retired. He had made his millions and had no interest in pursuing other illegal activity. He headed west and settled in Hot Springs, Arkansas. Charles Luciano arrived in Hot Springs in late March, and he hoped to lie low until the heat died down in New York. He was sorely mistaken. Within a few days, Thomas Dewey heard that Luciano was in Hot Springs. Dewey quickly

convinced a judge to issue a warrant for Luciano's arrest. On April 1st, two detectives caught Luciano as Luciano was walking into a bathhouse. They slapped cuffs on Luciano and threw him behind bars. For the next two and a half weeks, Luciano was embroiled in a legal battle. His attorneys fought extradition to New York, and they threatened to take the matter to the Supreme Court. Meanwhile, Luciano's gangster friends tried to intervene on his behalf. Supposedly, Oni Madden attempted to bribe a federal district attorney to help Luciano. And while all that was going on, Luciano could do nothing but sit in his cramped jail cell. Luciano's lawyers failed to get help through the courts.

Just after midnight, on April 18th, Dewey's agents escorted Luciano to the train station and sent him east. Nine hours later, Luciano arrived at Penn Station in Manhattan. That afternoon, Charles Lucky Luciano was arraigned in a New York courtroom on charges related to prostitution, and Thomas Dewey watched with pride. Luciano was just 38 years old. He had accomplished more, criminally speaking, than most people do in a lifetime, and he was a transformative figure in the mafia. But now he faced the prospect of watching the rest of his life sleep.

slowly fade away while he grew old in prison. From Black Barrel Media, this is Infamous America. I'm your host, Chris Wimmer, and this season we're telling the story of Charles Lucky Luciano. He was a notorious bootleggar, a gunman, a key player in a mob war, and the father of the American mafia. This is episode five, Operation Underworld. Luciano's trial began on May 11, 1936.

Thomas Dewey handled the prosecution, and he called 68 witnesses to testify that Luciano personally oversaw a major prostitution ring. Nearly all of Dewey's witnesses were prostitutes, madams, or bookers. Their testimonies painted a horrific picture of how prostitution worked in New York, and how Luciano ruled with an iron fist. After two weeks, Dewey rested the prosecution's case. It was now the defense's turn. Luciano's defense team claimed some of the witnesses had been threatened by Dewey to set up Luciano. In fact, the entire defense was that Charles Luciano was being framed, and he had absolutely nothing to do with the racket.

Throughout the proceeding, Luciano watched in stone cold silence, and then he agreed to take the stand and testify on his own behalf. On June 2nd, Charlie Luciano raised it. his right hand and swore to tell the truth, the whole truth, and nothing but the truth. Luciano's lawyer asked Luciano to go through much of his life. Luciano testified that the bulk of his financial success came from being a good gambler. He claimed that when he was younger, he got into craps and quickly moved into horsebedding and cards. When asked if any of his income came from prostitution, Luciano vehemently denied it.

He denied running a prostitution racket, denied knowing any prostitutes, denied paying for prostitutes, denied all of it. After half an hour of questioning, Luciano's lawyers gave the floor to Thomas Dewey. Armed with wiretap transcripts and other documents, Dewey went at Luciano hard. Dewey brought up Luciano's past as a dope dealer and his arrest in 1923. When discussing the bust, Dewey asked Luciano why he never went to prison for selling heroin. Luciano admitted that he gave the cops some information as a way to cut a deal. Dewey responded by calling Luciano, quote, Just a stool pigeon.

The comment rattled Luciano. He basically admitted that he broke the sacred coat of silence, Omerta, as a way to save himself. Luciano tried to calm himself down by denying that he continued selling narcotics after 1923, but it was clear that Dewey was gaining the upper hand. Dewey cross-examined Luciano for four hours. He forced Luciano to admit that he had done a little bootlegging during Prohibition,

as well as knowing other gangsters like Vito Genovese and Bugsy Segal. The admissions were somewhat damning, but they were just background information. Luciano denied any involvement in the matter at the heart of the. the case, prostitution. He said all his money in recent years came from gambling. With that, it was a wrap. The trial ended on June 6th. That evening, the jury retired to its chamber and deliberated. The next morning, the members told the court they had reached a verdict. Later that day, the jury announced that it found Charles Lucky Luciano guilty on all 62 counts of compulsory prostitution. On June 18th, the judge handed down his sentence, 30 to 50 years in prison.

If Luciano served every day of the minimum, he would be released when he was 68 years old. Charles Luciano was essentially sentenced to life in prison. Over the subsequent decades, legal scholars and mob historians have questioned whether or not Luciano actually operated a massive prostitution racket. While many agree that Luciano made money off sex workers, it's almost impossible to know if he was directly involved in the business. Some have argued that Thomas Dewey basically framed Luciano. Some of Luciano's gangster friends found it hard to believe that Luciano would bother

running a prostitution ring himself. Joe Bonano, one of the five bosses, thought it was most likely low-level enforcers using Luciano's name while extorting pimps or madame. Bonanno believed Dewey built a case against Luciano's name and reputation instead of Luciano's actions. Whether or not Luciano had a direct hand in controlling a citywide prostitution racket, the fact remained that he was going to prison. And that fact opened the door to the inevitable power struggle for control of the Luciano

crime family, which would pit Vito Genovese against Frank Costello. My relentless sleep problems have always come from an overactive mind. I lay in bed at night with my mind racing from one thing to another, and then of course I have a brainstorm about something new. That lights the fire and then I'm in real trouble. To calm my mind, the only things that have ever worked with any consistency are sleep gummies. Sleepy Time Advanced Gummies from mood.com come in various combinations of THC, CBD, and CBN. So you can get something. that's very low in THC, but higher in CBD, which helps turn off the stress, and CBN, which is the thing that makes you sleepy. The brain shuts up, the racing thoughts stop, and it's off to sleep.

Mood is federally compliant. The gummies are legal and delivered right to your door. At Mood.com, get 20% off your first order with our promo code, Infamous. Go to Mood.com and use the code infamous to get 20% off your first order. And they have a 100-day satisfaction guarantee. Mood.com promo code infamous. After the trial, Charlie Luciano was sent to Clinton Correctional Facility in Danamora, New York. Danamora is a small, isolated town near the Canadian border, and the prison was known as one of the worst facilities in the system.

It's almost always referred to simply as Danamora instead of its official name. and Luciano walked into the prison almost exactly seven years after prolific New York bank robber Willie Sutton walked out. Luciano would appeal his sentence, of course, but in the meantime, he tried to make the best of a bad situation. Luckily, many of the guards knew who he was and left him alone. Luciano became influential with other inmates. They approached him to ask for advice or just to pay respect, and he spent most days watching baseball and playing cards. Throughout 1937, Luciano appealed his sentence. Each ruling came back the same, denied. By the end of the year, Luciano had exhausted all of his appeals. Barring a miracle,

Luciano would not be a free man for a long time, if ever. So he turned his attention toward choosing his successor. Before he was sent away, Luciano was already thinking about who should be the new boss. There were two possible candidates, Vito Geneviz, Luciano's underboss, and Frank Costello, Luciano's Consolieri. Vito Genevese was cold and ruthless. More than anyone in the family, Genevese desperately wanted to be the boss. And since he was already under boss, second in command, he believed he had the right to step in for Luciano. Meanwhile, Frank Costello was a bit more calculating and discreet with his criminal ambitions. Costello's crew made money through slot machines, which brought in quite a bit. But it was his role as consulieri where Costello proved his true

value. Throughout the early 1930s, Costello had inserted himself into the Tammany Hall political machine. He forged relationships with Democratic politicians and used his influence to help them win elections. In turn, they did favors that helped the family. Costello knew that discretion and diplomacy went further than violence, and in time, he earned the nickname, the Prime Minister. Luciano had known both men since they were all teenagers in the Five Points Gang, and even though Luciano had named Vito Genevese his second in command, he leaned toward Frank Costello to take over as boss. Before heading to prison, Luciano named Costello, acting boss, and gave Costello control over the day-to-day operations of the family. At the time, the move was intended to be

temporary, because Luciano expected to be out of prison sooner rather than later, whether it was through an appeal or some other way. Regardless, Vito Genovese was not happy with Luciano's decision, and Costello knew that Genevese wasn't going to accept it quietly. Genevese ran a notoriously dangerous crew, and he could start a civil war at any moment. Costello and Luciano obviously didn't want a civil war in the family, which would tear the empire apart. And luckily for both men, an unlikely guardian angel saved them from that fate. With Luciano in prison, Thomas Dewey made Vito Genovese his next target. But instead of going after Genevese for tax evasion or racketeering, Dewey went after him for murder.

Dewey had evidence which linked Genevise to the 1934 murder of another gangster. Genevese learned that an indictment was coming soon, and he fled town. But Genevese seemed to have learned a lesson from Luciano. When he left New York, he didn't head upstate or a few hundred miles away to Arkansas. He left the entire country. Genevese went all the way to Sicily, and with Genevese gone, the transition of power in the family was easy. In 1938, Luciano officially named Frank Costello as the acting boss. Luciano was confident that Costello would be able to run the various businesses without any problems from the law,

and he was right. For 12 years, Costello ran the family relatively smoothly, until the U.S. Congress dedicated serious resources to dismantling organized crime. Over the next few years, Luciano lived mostly as inmate number 92186. Costello and Meyer Lansky made sure Luciano received information on business and a cut of the profits. And since Luciano had exhausted his appeals, the only other thing he could do was pray for a miracle that would let him out of prison. In December, 1941, his prayers were answered. A catastrophe for the rest of the country was a miracle for Lucky Luciano. By the fall of 1941, 44-year-old Charles Luciano had served five years of his prison

sentence. He had survived Dan Amora's swelteringly hot summers and brutally cold winters. According to the law, he would be in there for at least another 25 years. Nothing short of a Miracle would see him released before he was in his 60s. And then, on the morning of December 7, 1941, Japan attacked the U.S. naval base at Pearl Harbor. The next day, December 8th, Congress declared war on Japan. A few days later, Japan's allies, Nazi Germany and fascist Italy, declared war on the U.S., and America had officially entered World War II. In the months that followed, Germany sent him to the United States.

submarines called U-Boats to prowl the Atlantic Ocean. While America mobilized its military, the U-boats targeted American merchant ships which carried supplies to Britain and France. German subs attacked more than 100 American vessels in early 1942. Attacks on the open ocean were bad enough, but American leaders became increasingly worried about attacks at home. And those attacks didn't have to take the form of bombardments by, German subs to do damage. Spies and saboteurs could wreak just as much havoc on American ports. The SS Normandy was a French luxury ocean liner that had been docked at New York's Pier 88 for more than two years. It arrived in the United States shortly after World War II broke out in 1939,

and the people who controlled the ship asked to remain in safer waters to avoid Nazi U-boats. But after the attack on Pearl Harbor, the U.S. government seized the massive ship and began converting it into a transport vessel that would be used to send soldiers to Europe. At 2.30 p.m. on February 9, 1942, a fire broke out on the ship. Firefighters, sailors, and construction workers spent hours fighting the blaze. Smoke billowed from Pier 88 and hovered over New York skyline, and it looked like America had been attacked again. Finally, at around 6 p.m., firefighters managed to gain control of the flames, but the damage was done. The ship partially rolled onto its side and now tilted at a 45-degree angle.

Portions of its decks were underwater, and the ship was totally disabled and unusable. People instantly suspected sabotage. Although witnesses claimed that sparks from a welding torch caused the fire, the authorities were convinced that German spies played a part. A few months later, the FBI arrested Nazi spies who were trying to infiltrate New York. Paranoia was sky high, and rightfully so. U.S. naval intelligence knew that the ports were vulnerable, and as they surveyed the area, they noticed that the majority of the men who worked on the docks were either Italian immigrants or Italian Americans. Italy and Germany were staunch allies, and naval intelligence feared that the Italian dock workers might be loyal to Italy's dictator Benito Mussolini. Lieutenant Commander Charles

Haffenden, the head of New York's Naval Intelligence Office, was desperate to keep the ports safe. Haffenden said, quote, I'll talk to anybody, a priest, a bank manager, a gangster, the devil himself. This is war. American lives are at stake. Intelligence quickly understood that the mob controlled the docks through the labor union rackets. Everyone who worked at the ports had to have a union card, and the five families controlled who received a card. So, naval intelligence took Haffenden's quote literally. They talked to a gangster. Intelligence agents contacted the New York District Attorney's Office because of its history battling racketeers. The DA's office facilitated a meeting with a gangster named Joe Lanzah.

Lanzah was a captain in the Luciano Crime family. His crew controlled the seafood workers union at the Fulton Fish Market. At the time, the Fulton Fish Market was the largest seafood distribution center in the U.S. Federal agents recognized Lanzah would have some serious poll. Lanza met with the agents at the end of March 1942. The agents pitched their concerns, specifically that saboteurs might destroy ships or agitate for labor strikes. They wanted Lanzah to allow agents to work on the docks with regular union workers so they could keep an eye out for possible spies. They also wanted information from ship captains about possible U-boat refilling stations in the Atlantic Ocean. At the time,

Lanzah was facing criminal charges for extortion, and he saw an opportunity to save himself. So he readily agreed to help the military, with the hope that it would get the DA to back off of his case. But Lanzas' help was limited. He explained that while he could get federal agents into the Fulton fish market, he had no sway in other ports, like Brooklyn. Those were controlled by other families. but Lanzah knew the man who could, quote, snap the whip of the entire underworld. If Naval Intelligence wanted men in every New York port,

they were going to have to go up to Dan Amora and visit Charlie Luciano. In April 1942, Naval Intelligence decided to reach out to Luciano, but they knew they couldn't just drive up to Dan Amora and request a sit down. If they were going to be taken seriously, they needed to go through the proper channels. Instead of reaching out to Frank Costello, Naval Intelligence approached Luciano's closest friend, Meyer Lansky. When agents approached Lansky, they were concerned that Luciano wouldn't play ball. But Lansky assured them that Luciano and his family were loyal to America and not to Mussolini.

Lansky agreed to talk to Luciano. In mid-May, Luciano learned he was suddenly being transferred out of Danamora to a prison called Great Meadow. Though he was confused, he certainly didn't mind leaving the prison that was sometimes called New York's Little Siberia. Luciano arrived at Great Meadow on May 12th. Three days later, he was told he had visitors. When he went to the visitors' room, Luciano was shocked to see his lawyer and Meyer Lansky waiting for him. Lansky made the pitch.

Luciano thought about it, but had reservations about the outcome of the war. Specifically, he worried what would happen to the mafia if Mussolini won. But Lansky countered about the future if America won, and the power it would give to Luciano. After careful consideration and a realization that this might be his ticket out of prison, Luciano agreed to help the United States in World War II. Over the next few months, Luciano spread the word throughout the underworld that the mafia was now part of the war effort. Gangsters like Frank Costello and Joe Adonis visited Luciano in prison, and Luciano gave them orders that everyone working on the docks needed to keep an eye out for suspicious people, as well as to stop any kind of labor agitation. With a simple word, Luciano was able to convince the other bosses that they needed to follow suit.

Meanwhile, Luciano dispatched his toughest enforcers to make sure everything was on the up and up. A union leader named Harry Bridges found out the hard way that Luciano was serious. Bridges went down to the docks with the intention of starting a strike. Joe Lanza, the Luciano captain who pointed the Navy toward his boss, assaulted Bridges and firmly convinced him to change his mind. There would be no damn strikes after Luciano had issued the order. By the start of 1943, Luciano had proved his worth. Through Operation Underworld, as the covert mission was called,

Luciano kept the workforce at the ports in line, and he allowed federal agents to keep their eyes and ears out for spies. Eventually, the agreement extended to bars and hotels throughout New York. If anyone said something that could help the Nazis, the mafia was aware of it. As the effort progressed at New York's waterfront, the Allied Powers planned the first invasion of Europe. Sicilians, who had been invaded regularly since humans learned how to nail pieces of wood together to create a boat, would not have been surprised to learn that they would be ground zero for the Allies' first assault in Europe.

The Allies were targeting Italy and North Africa first, and the invasion of the Italian mainland, known as Operation Husky, would start on the island of Sicily. In the spring of 1943, Luciano heard about the upcoming invasion from Meyer Lansky. When he did, Luciano saw another opportunity to hopefully shave off time from his sentence. In May, he told Lansky that he could reach out to the Sicilian mafia to help coordinate with Allied soldiers. He also said he could give naval intelligence maps and locations on where allies should land. But Luciano wasn't done yet. He even proposed that he, Charlie Luciano, go in with the soldiers and personally lead the way.

The idea was exactly as crazy as it sounded. But surprisingly, it wasn't immediately rejected. In mid-May, 1943, Meyer Lansky went to Lieutenant Commander Haffenden with Luciano's pitch to personally help with the upcoming invasion of Sicily. To Lansky's shock, Haffenden loved the idea. The truth was, the American and British militaries had considered reaching out to the Sicilian Mafia for help. Military intelligence knew that the Mafia and Mussolini despised each other, and the allied

powers hoped to establish a kind of, the enemy of my enemy is my friend, relationship with the gangsters. Unfortunately, those above Hafenden weren't as keen on the idea of using Luciano. They weren't convinced that Luciano had the kind of leverage with the civilization. Sicilian mafia since he hadn't been to Sicily in decades. And they were also skeptical that Luciano was knowledgeable of German strength in Sicily. Hafenden may have liked the idea, but his superiors rejected it. On July 10, 1943, Allied forces invaded Sicily. It took only a month for Allied troops to secure the island. During that time, Mussolini's fascist regime fell, which ultimately led to

Italy's exit from the war. For Charlie Luciano, all he could do was read about the Allies' success from his prison cell and hoped that Uncle Sam wouldn't forget about him when the war ended. In April 1945, Nazi Germany surrendered, and the European theater of World War II was over. In New York, Charlie Luciano decided the time had come to leverage his help in the war effort as a means to secure his freedom. In May, Luciano filed a petition for clemency to the New York State Parole Board. Luciano reached out to Lieutenant Commander Hafenden and asked if Hafenden would write a letter on his behalf. Hafenden was more than happy to help Luciano, and he supported Luciano's claim about his cooperation during the war.

However, the rest of naval intelligence refused to support Luciano. The Navy was a little embarrassed that it turned to criminals to maintain order. on the docks, and it refused to release information to the parole board. But as luck would have it, the Manhattan District Attorney's Office had documentation that supported Luciano's claims. Luciano's lawyers had worked closely with the DA's office throughout the war in order to make sure everything was above board. Naval intelligence may have been playing hardball, but the district attorney wasn't. After a long and arduous investigation, the Parole Board agreed

that Luciano should be granted clemency because of his role during the war. It was great news for Luciano, but there was a major catch. Luciano would be deported from the United States. He would be free, but he could never again set foot on American soil. Luciano was devastated when he heard the news. The cost of freedom was high, and his only hope was that the governor of New York would change the ruling and allow him to stay in the U.S. Unfortunately for Luciano, the governor of New York was Thomas Dewey, the prosecutor who had sent him to prison.

Dewey was elected governor in 1942, largely thanks to his work against the gangsters of New York. Luciano thought that Dewey owed him. After all, Luciano was the driving force behind saving Dewey's life a decade earlier when Dutch Schultz wanted to kill the DA. But Dewey didn't see it that way. It meant little to him that Luciano vetoed an assassination contract. In Dewey's mind, Charlie Luciano was a bad guy, and bad guys should be punished. But Dewey did acknowledge that Luciano helped America defeat the Nazis and the Italian fascists. Exactly how much Luciano helped has been up for debate in the decades that follow.

But at the time, lots of people said Luciano did quite a bit. In the end, Dewey agreed with the parole. board. He granted clemency and ordered Luciano to be deported. At the beginning of February 1946, Charlie Luciano was transferred to a prison cell on Ellis Island. It had been almost exactly 40 years since he had landed at Ellis Island as a boy. For generations, Ellis Island was the primary entry point in New York for people who wanted to move to America. Now, it was the last place Luciano would see before he was forced to leave. As Luciano waited for a ship to take him to Sicily, his mind churned. He viewed his deportation as an obstacle, not a defeat. He was only 48

years old. There was plenty he could do from abroad. In another stroke of luck, there was another island that was becoming a hub of international criminal activity, and it was just 90 miles from Florida. The casinos of Las Vegas were already proving to be money printing machines for the mob, and now the bosses wanted to do the same thing in Cuba. Next time on infamous America, Luciano sets up headquarters in Cuba, but he learns that being out of New York makes it extremely difficult to control his family. During an important criminal conference in Havana, Luciano and Meyer-Lansky must make a difficult decision regarding one of their closest and oldest friends.

That's next week on the season finale of the Lucky Luciano story here on Infamous America. Members of our Black Barrel Plus program don't have to wait week to week for new episodes. They receive the entire season to binge all at once with no commercials, and they also receive exclusive bonus episodes.

Sign up now through the link in the show notes or on our website, blackbarrelmedia.com. Memberships are just $5 per month. This series was researched, written and produced by Joe Garrow. Original music by Rob Valia. Early research and writing by Michael Byrne. I'm Chris Wimmer.

Thanks for listening.