Infamous America - LUCKY LUCIANO Ep. 1 | “Five Points Gangster”

Episode Date: March 19, 2025

In the late 1800s, millions of immigrants come to the United States for the opportunity for a better life. Among those who come from Sicily is a boy named Salvatore Lucania who will be known as Charles “Lucky” Luciano. Luciano grows up on the mean streets of New York’s Lower East Side and gravitates toward a life of crime. When Prohibition begins, Luciano becomes a prominent bootlegger and finds a mentor in Arnold Rothstein. 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

Possibly no phrase fits life in organized crime better than survival of the fittest. Mobsters constantly vied for power and would do whatever it took to grab it. Only the smartest and most ruthless could make it to the top. By 1922, the man at the top of the crime hierarchy in East Harlem and much of Brooklyn was Giuseppe Joe Mazaria. Joe was a Sicilian immigrant who came to America in the late 1910s, and quickly rose up the ranks of Manhattan's underworld. To do so, Joe did whatever it took,

and he made lots of enemies in the process. Joe had dropped quite a few bodies and betrayed quite a few people to achieve power in the streets, and his rivals quietly plotted his demise. It was only a matter of time before someone went after him. On the afternoon of August 8, 1922, Joe Masaria left his Lower East Side Brownstone home and stepped on to Second Avenue.

It was a nice summer day, and Joe wore a straw hat and a summer suit. He started walking down the street, glancing around casually, until his gaze landed on two men who were exiting a nearby cafe. They rushed toward him, and they drew handguns as they approached. Joe immediately recognized one of the men, Umberto Valenti. Valenti was a well-known assassin, nicknamed the Ghost. Valenti had worked for one of Joe's rivals, but Joe had ordered the murder of the rival a few months earlier. Now Valenti the ghost was there to settle the score. As the assassin started firing,

Joe took off his straw hat and raised it up as if it would miraculously stop the bullets. Valenti fired three times. All three bullets missed their target, and no one was more surprised than Joe Maseria. But Valenti and the other gunman didn't have time to fail. finish the job. A crowd began to form, and all the gunmen could do was run to the getaway car and speed away. As Joe Masaria returned home and reeled from his near-death experience, his thoughts quickly turned to vengeance. He couldn't let an attempted assassination go unanswered. But Joe was smart, and he needed to buy himself some time to make sure that his response wouldn't fail. A few days later, Joe called a sit-down with Valenti.

he pitched it as a chance to clear the air. Joe and his men, and Valenti and his men, met at a corner cafe on 2nd Avenue. No sooner had they all sat down, then Valenti realized the meeting wasn't to talk peace. It was an ambush. Joe's men raised their pistols and began to fire. As bullets whizzed by, Valenti ran out of the cafe and into the street.

Joe's gunmen followed. They fired wildly into the busy street, and, tragically, a little girl was struck by a stray bullet. Valenti rushed up to a cab, jumped onto the cab's running board, and told the driver to take off. As the cab barreled down the street,

Valenti turned around and saw one of Joe's gunmen calmly walk into the middle of the street and raise his gun. Valenti pulled out his pistol and aimed at the lone gunman in the street. Before he could fire, a bullet struck Valenti in the chest.

Valenti fell to the side of the cab and died almost immediately. By the time the police arrived, Joe Mazaria and his assassins were gone. A teenager told an officer that the explosion of violence was one of the coolest things he had ever seen. He especially couldn't believe

how calm the lone gunman in the street looked as he emptied his clip. Meanwhile, another witness described that gunman as dark, short, and neatly dressed. According to Gangland lore, the calm, ice-cold gunman was Charles Luciano. At the time, Luciano was nothing more than a low-level gunman, bootlegger, and racketeer who worked for Joe Mazaria.

But in less than a decade, he would go on to completely revolutionize the mafia in the United States. 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 bootlegger, a gunman. a key player in a mob war, and the father of the American mafia. This is episode one, five points gangster. Between 1890 and 1920, roughly four million mainland Italians and Sicilians brave the journey across the Atlantic Ocean to America.

For the majority, it was because of economic hardship due to political changes. In 1861, the various kingdoms along the Italian peninsula unified in a a single nation. Thirty years after unification, many peasants and laborers found no economic prosperity, and they saw America as a chance to start over. One of the Sicilian families who took a chance on a new life was the Lucanilla family. Patriarch Antonio spent his days in Sicily as a sulfur miner. But after years of toiling with little to show for it, he decided it was time to pack up his family and head for greener pastures. In May 1907,

Antonio, his wife, and their three children landed in New York City. The youngest Lucanilla, Salvatore, was nine years old when his family arrived in the United States. No one could have imagined he would one day reshape organized crime as we know it,

nor that he wouldn't do it as Salvatore Lucanilla, but as Charles Lucky Luciano. To get there, Salvatore would grow up fast on the streets of the lower east side of Manhattan. Like many new arrivals to New York, the Lucanilla family found the conditions were less than ideal. Young Salvatore and his family lived in cramped, tenement housing. Many of the small three-bedroom apartments had no hot water and no indoor plumbing.

The walls were barely painted, and the windows did little to keep out the cold. Escaping to the outdoors proved to be no better. A rancid odor made up of sewage and raw food hovered over the neighborhood. It was as if Salvatore's father, Antonio, had never left the sulfur mines. Still, the family hoped that hardship would eventually make the move worth it, especially for their children. Unfortunately, Salvatore struggled to adapt to life in America. He didn't speak English, and he had a hard time mingling with other Italians.

His Sicilian dialect clashed with mainland Italian. He was frustrated that no one could understand him and he couldn't understand others. And the problem was painfully apparent at school. Salvatore's teachers only spoke English. Soon, he fell behind in his studies. His frustration and anger grew, and he decided there was only one solution to the problem. Stop going to school. Young Salvatore knew he was never going to be an academic or a scholar.

School just wasn't for him. He realized that his education would come from the streets, and he wasn't the only one. Many kids his age gravitated toward a life on the streets. Kids, some as young as six, formed small street gangs and raised hell. Salvatore ran with a few young street gangs and committed petty crimes. They picked the pockets of strangers in crowded places and broke into random apartments to steal whatever they could find. In back alleys all over the city, the street gangs ran illegal craps games. In no time at all, Salvatore earned his degree from the School of Hard Knocks.

But from an early age, he knew there were bigger and better ways to earn money. He was observant, and he understood the social dynamics within the neighborhood. The Lower East Side was a melting pot, a place filled with Sicilian, Italian, Irish, and Jewish immigrants. Among that group, Jewish. Jewish kids were at the bottom of the pecking order, and Salvatore saw an unsavory opportunity. Around the time he became a teenager, Salvatore went to Jewish kids and offered protection from the Irish and Italian kids. Of course, the protection came with a price. Many young Jewish kids paid Salvatore for his services, but not everyone. One afternoon, Salvatore approached

a young Jewish boy named Meyer Sojolansky. Meyer had immigrated with his family in 1911, and he was not afraid of the older Sicilian boy. When Salvatore stopped Meyer on the street, he told Meyer he would protect him for five cents a week. Meyer looked Salvatore in the eye and told him what he could do to himself. At first, Salvatore was taken aback, but the shock quickly disappeared, and Salvatore became impressed. Instead of giving Meyer a beating, Salvatore decided to make him a friend. Like Salvatore, Meyer would eventually change his name to something a little bit easier for Americans to say,

Meyer Lansky, and he and soon to be Charles Luciano would become criminal partners for life. As a teenager, Salvatore Lucania spent the majority of his days as a street-wise, petty criminal. Technically, he was still in school, but with each passing week, he skipped more often than he attended. becoming a delinquent didn't sit right with Salvatore's parents, and whenever Salvatore got into trouble, he received a beating from his father. But the beatings did little to correct Salvatore's behavior. Instead, more drastic measures were needed. In 1911, 14-year-old Salvatore was sent to a special school for truance in Brooklyn.

The hope was that if Salvatore was away from the troublemakers in the Lower East Side, he would straighten out. It didn't work. Four months later, Salvatore was back on the streets and committing petty crimes. When he returned, he decided he was done with school forever. But not long after returning from the special school in Brooklyn, Salvatore started making some legitimate money. He got a job working as a delivery boy for Goodman's hats. Initially, he earned $5 a week. Then it became seven. Salvatore worked for Goodmans for the next few years and only quit after striking it big at a dice game.

But even as he worked an honest job, Salvatore had zero interest in putting aside his criminal endeavors. And it was around that time that Salvatore took his first step into narcotics. It isn't clear exactly when Salvatore first came in contact with narcotics, but by the mid-1910s, he was very much aware of their popularity, especially heroin and cocaine. At the time, neither heroin nor cocaine were considered illegal substances. In fact, both were used for medical purposes. Heroin was sometimes prescribed as a cough suppressant,

and cocaine was used as a local anesthetic. But like all drugs, abuse was rampant. The result was an illegal black market drug trade, and Salvatore saw yet another opportunity to make money. Some time around 1915, Salvatore began running drugs for a local dealer. But his time working for the unnamed drug peddler didn't last long. At some point in 1916, 18-year-old Salvatoree was sent to a tavern to deliver heroin to a prostitute. Unbeknownst to Salvatore, the prostitute was an informant for the NYPD.

She eventually gave the police Salvatore's name, and he was arrested. At the end of June, 1916, Salvatore was sent to New Hampton Farms Reformatory. His sentence was eight months, but he got out in six, even though a probation officer noted that Salvatore had a, quote, definite criminalistic pattern of conduct. Still, by the start of 1917, Salvatore was a free man. When he was back on the streets, his reputation grew. Word spread quickly that Salvatore was a stand-up guy. While in prison, he kept his mouth shut and didn't name names.

He did his time like a man, and that was a big deal in the underworld. But while his reputation grew, thanks to his time at the Reformatory, the time also told him that he needed to make a drastic change. Supposedly, other inmates called him Sal, or Sally. Salvatore didn't like the feminine connotation associated with the nicknames. Moving forward, he would call himself Charles. And before long, he would change his surname to Luciano. Salvatore Lucania was out and Charles Luciano was in.

With a new name, he joined a new gang, the legendary Five Points Gang. The Five Points Gang was founded sometime in the 1890s by a man named Paul Kelly. Paul Kelly was actually an Italian immigrant who changed his name to sound Irish with the hope of fitting in. The concept and the name of the gang traced their roots back to the regional and ethnic gangs of the infamous Five Points neighborhood in Lower Manhattan. Many of the gangs have been immortalized in books and movies and had names like the natives, the dead rabbits, the plug uglies, and the Bowery boys, and so on. Paul Kelly became a well-known boxer in the area who sold his fists to the notorious Tammany Hall political machine. In other words, he had no problem

beating up people to get them to vote for the Tammany ticket. Paul recruited incoming Italian and Irish immigrants, though mostly Italian. Soon, voter intimidation gave way to other forms of criminal activity. By the mid-1910s, the gang was one of the most feared in Lower Manhattan. When Charles joined the Five Points gang, he joined a brotherhood of up-and-coming gangsters, like future mob bosses, Frank Costello, and Vito Genovese. For a brief time, Alphonse Capone overlapped with Luciano in the gang, before Capone's friend, Johnny Torio, himself a five-point ally, summoned Capone to Chicago to help build a criminal empire.

Though Charles Luciano was now part of a major street gang, he yearned for more. Small-scale drug dealing and muscle for higher work was fine, but going into his 20s, he wanted to carve out his own criminal territory. Luckily for him, the U.S. government was about to hand him and many others like him a golden ticket. On January 16, 1919, the 18th Amendment to the U.S. Constitution was ratified by the majority of states. The production, distribution, importation, and sale of alcohol was officially prohibited in the U.S. Later that year, Congress enacted the Volstead Act, which established the rules and punishments for violating the 18th Amendment.

The Volstead Act went into effect January 17, 1920. Alcohol was now illegal in America. The road to prohibition was long and arduous. Temperance and anti-saloon groups were active around the country throughout the 1800s, but with little success. Any attempt to curb America's heavy drinking habit was generally relegated to local communities. But by the early 1900s, the movement had gained a lot of momentum. For years, families had suffered the negative effects, and not just from the quantity, but from the quality, too. The stuff they drank back then would horrify most modern drinkers. The hope was that the U.S. would become a better,

more harmonious place, now that booze was illegal. Instead, it had the opposite effect, and more. Nobody stopped drinking, and Prohibition opened the door for men like Charles Luciano to make millions. To protect their illegal alcohol businesses, gangsters would do anything, and they left a trail of bodies in their wake. For the first two decades of the 20th century, street gangs seemed to be fairly fluid. Members appeared to come and go without many repercussions. That looks like the case for Luciano, when Provinciales. prohibition went into effect. In 1920, he left the five points gang and headed up to East Harlem

to work for an Italian gangster named Giuseppe Joe Mazaria. Luciano became one of Masaria's gunmen. In time, he would help run some of Joe's gambling and extortion rackets. But for the most part, Joe Mazaria used Charles as a hired killer. In 1922, Joe organized the murder of one of his rivals. A top assassin for the rival wanted revenge, and he tried to kill Joe as Joe walked out of his house on 2nd Avenue. Joe survived the attempted murder and then retaliated. In August 1922, gunmen killed the assassin, Umberto Valenti, on the corner of 2nd Avenue and East 12th Street, and it's widely believed that Charles Luciano was one of the gunmen. While working for Joe Maseria, Charles made a decent living, but he wanted more.

He wanted in on the action of prohibition, and he wanted to be associated with people who saw the true potential of the prophets that could be made from prohibition. Joe Mazurrea didn't seem to have what Charles was looking for, but Charles knew who did, his old friend, Meyer Lansky. Over the years, Charles and Meyer continued to keep up their friendship, even though they associated more and more with gangs connected to their own ethnicities.

Meyer, for example, became close with a dangerous young Jewish gangster named Benjamin Bugsy Siegel. Meyer took Bugsy under his wing, and Bugsy remained by Meyer's side. Charles wanted to work with his friend, but Joe Maseria wouldn't allow it. Joe, being of the older generation, didn't approve of working across ethnic lines. He was wildly anti-Semitic, and he said Charles couldn't work with Jewish gangsters. But Charles refused to listen. and it just so happened that Meyer Lansky had come into contact with one of the most successful underworld bosses of the era, Arnold Rothstein.

By the time Prohibition began, Rothstein was one of the most famous gamblers in America. He was a wizard with numbers, and he built a career on betting on horse racing and other sports. For the most part, he liked to avoid the spotlight. But then in 1919, he was indicted for fixing the World Series. Allegedly, he provided money which was used to bribe players on the Chicago White Sox to lose games. He was never convicted, and his involvement in the Black Sox scandal, as it was called, remains a hot topic of debate to this day. Even though his name was in the papers more than he liked, that didn't stop Rothstein from seeing an opportunity to get into the sale of illegal alcohol. In fact, Rothstein had visions that no other gangster had.

While most crime leaders began quietly selling small batches of alcohol around the city, Rothstein saw it as a major business. For him, it wasn't going to be some casual side gig. It was going to be a full-scale operation. He was determined to become an alcohol kingpin. But to do that, he needed men. Rothstein always kept his ear to the streets, and he knew who to enlist. It isn't clear when Charles Luciano met Arnold Rothstein,

but it appears to have been early in prohibition and through his friend Meyer Lansky. Supposedly, Meyer sat down with Rothstein, and Rothstein laid out his plan. In short, Rothstein was going to buy the finest scotch whiskey directly from distillers in England and Scotland. The whiskey would travel across the Atlantic Ocean, and Rothstein's men would offload it at quiet spots along the American East Coast and transported inland. Rothstein needed workers, and he trusted Lansky. Lansky, in turn, trusted his friend Charlie Luciano to help him build the small army of workers who would be needed to make the business successful.

It took little to convince Luciano to start working for Rothstein. Rothstein was a name that rose above the neighborhoods of the Lower East Side or East Harlem. If you were connected to him, you could have your run of Manhattan and beyond. Most likely, Charlie started working for all. Arnold Rothstein somewhat quietly to avoid any fallout from his other boss, Joe Maseria. What exactly Charlie did in the first days is also a little obscure.

We know that Rothstein needed young men to smuggle his high-quality scotch off the Atlantic coast, and it's likely Charlie participated in the nighttime missions. Rothstein quickly became a mentor to Luciano and Lansky. Rothstein advocated for staying out of the limelight, to do business with discretion. Being flamboyant and having your picture in the papers would only bring unnecessary attention. And like Lansky did for Luciano, Luciano did for his friend Jack Legs Diamond. Supposedly, it was Luciano who first introduced Diamond to Rothstein. Diamond became Rothstein's bodyguard and quickly proved his worth by foiling a kidnapping plot by an out-of-town gangster.

In the first couple years of prohibition, the bootlegging business was going to be. going well. But Luciano wanted more. He never lost his interest in selling drugs, and his re-entrance into the heroin trade would have disastrous results. The exact details of Luciano's heroin operation are a bit of a mystery. There are rumors that he smuggled heroin by way of hats, a tricky learn during his hat delivery days as a teenager. It's likely Charlie kept the details a secret by design. Most gangsters look down on drug dealers. Prostasis, Institution, illegal booze, and illegal gambling were fine. But hard drugs were usually a bridge too far. Charlie rolled the dice, so to speak, and he lost. In the spring of 1923, Charlie began selling heroin to a man named John Lyons.

They usually met in a pool hall on East 14th Street, and on June 2nd, Charlie sold John two ounces of morphine. A few days later, they met again at the pool hall, and Charlie sold John. some heroin. The next day, Charlie returned to the pool hall to sell John even more heroin. But that day, Charlie looked down at John's hands and his eyes went wide. In one hand, John held a gun. In the other, he held a police badge. Charlie looked around for an exit in the hope that he could make a run for it, but instead, he saw a second lawman standing up from a nearby booth. Charlie raised his hands and accepted his arrest. At the police station, he had to think fast. This was his second arrest for drug dealing, which meant he faced a possible 10-year prison sentence. And

word would be out on the streets that Charlie Luciano was nothing more than a dope peddler. Worst of all, there was only one way out of his predicament. He had to talk. But that was when Luciano had a moment of inspiration. It wasn't a perfect solution, but it would give him options. When asked for the names of his suppliers, Charlie gave the agents an address instead. When law enforcement went to the address, they found a massive cash of narcotics worth between $75,000 and $150,000. On the high end, it would have had a value of more than $2.5 million today. It was an impressive hall, and the cops loved it. As a result, Charlie wasn't charged with a crime. He was free to go.

His plan had worked, but it had only worked because of a painful reason. The seized heroin didn't belong to Charlie's suppliers. It was Charlie's personal stash. Charlie didn't want to be labeled a rat, so he gave up his own supply. Essentially, he snitched on himself. But that didn't mean the criminal underworld would believe him. When Charlie went back to business, his reputation was tarnished. people didn't want to buy alcohol from a low-down dope dealer,

and since Charlie had escaped punishment, he was suspected of being a rat, the label he had hoped to avoid with his Hail Mary plan at the station. In the summer of 1923, Charlie Luciano needed a public relations makeover. His friends Meyer Lansky and Arnold Rothstein became his crisis management team, and Meyer had a brilliant idea.

Charlie needed to make a grand gesture, and it just so happened that the biggest boxing match of the year, a fight that would turn out to be historic, was happening in three months. Jack Dempsey had been the heavyweight champion of the world since 1919, and he was scheduled to meet Luis Firpo for a title bout at the polo grounds in New York on September 14th. Meyer Lanski proposed an idea to Charlie Luciano.

Charlie should buy tickets to the star-studded event for a bunch of influential people, gangsters, politicians, businessmen, high-ranking law enforcement, everyone. And he did. Luciano spent roughly $25,000 on 200 tickets. Among the gangsters who went to the fight because of Charlie were Al Capone, Johnny Torrio, and Boston crime boss, King Solomon. When Luciano arrived at the fight, he had received a fashion makeover, courtesy of Arnold Rothstein.

Rothstein advised Luciano to what he was. wear something a little more conservative, a little less flashy. With Rothstein's approval, Charlie arrived wearing a crisp but simple gray suit, a gray fedora, and a blue silk tie. Charlie looked like a businessman, not a drug dealer or a street hustler. Years later, he credited that evening with completely changing how he dressed for the rest of his life. Rothstein had reshaped Charlie's image, and the boxing match lived up to its billing to help the grand gesture. It only lasted two rounds, but they were wild. Dempsey knocked Furpo down seven times in the first round,

and then Firpo countered with a combination of punches that were so strong, they knocked Dempsey clear out of the ring. The champ sailed through the ropes and into the people closest to the ring, but he was able to climb back into the ring before the referee counted him out. In the second round, Fearpo blasted Dempsey with a barrage of punches, but Dempsey rallied and landed a. knockout punch that ended the fight. Jack Dempsey kept his heavyweight title, but the real winner that night was Charlie Luciano. His grand gesture worked, and he was back in business.

Over the next few years, Charlie expanded his bootlegging operation and various gambling rackets. By 1925, he was earning more than $12 million a year. For a while, he continued to bounce around from crew to crew. But in 1927, he refocused on his allegiance with his old boss, Joe Masaria, though that didn't stop Charlie from quietly working with his closest friend and ally Meyer Lansky. It was a dangerous line for Charlie to walk, but Charlie didn't care. Charlie became less and less interested in sticking to the strict, old-school idea of working only with Sicilians. He continued to work with Rothstein, too, though more so in the distribution of drugs than alcohol. Even after that crazy summer of 1923, Charlie didn't give up on the drug business,

probably because Rothstein never gave up on it. In fact, by 1928, Rothstein was slowly leaving alcohol behind in favor of smuggling heroin and opium. As long as they played it smart and quiet so as not to ruin their images, Luciano and Rothstein were happy to keep going with the drug game. But their association wouldn't last much longer. Arnold Rothstein was, at his core, a gambler. He loved chasing that rush and found himself on gambling benders, but it was only a matter of time before his luck ran out. In September 1928, Rothstein sat down for a multi-day card game.

By the time it ended, he was down $340,000. That would be more than $6 million today. Rothstein had a good reputation for paying people back. But two months later, he hadn't paid off his enormous debt. On the evening of November 4th, Rothstein went to the Park Central Hotel for a meeting. Gunman ambushed him and shot him multiple times. He was rushed to the hospital, and he survived for two days. When the police questioned him, Rothstein refused to name names.

Allegedly he cracked a joke at the end and said his mother did it, though that could easily be an invention of gangland lore. There were plenty of suspects in the murder, but no one was convicted. The power vacuum that was created by Rothstein's murder was immense. The man known as the brain and the big bankroll was gone, and everyone wanted a piece of his crumbling empire. That included, of course, Joe Maseria. And Maseria wanted to make a bigger power play

than just scooping up parts of Rothstein's business. Before long, he would go to war with a powerful rival for control of, of an empire, and it would be one of the bloodiest conflicts in the history of American crime. Charlie Luciano would hold the unique distinction of being both a victim and the victor. Next time on Infamous America, it's the beginning of the Castellarer-Morreze war between the gangs of Joe Mazaria and Salvatore Maranzano. Charlie Luciano has a near-death experience from which Meyer-Lanski allegedly gives him his famous nickname. And Charlie, slowly but surely, realizes that his vision for a different style of organized crime

means betraying those closest to him. That's next week 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 Valier. Early research and writing by Michael Byrne. I'm Chris Wimmer. Thanks for listening.