21 Real-Life Gangsters on Boardwalk Empire

Want to know the stories behind the real Boardwalk Empire season 5? You've come to the right place...

SPOILER WARNING: This Boardwalk Empire history article may tell you how some of your favorite characters end up. Continue at your own risk…

Up against the wall, you punk bastards! Time for your mug shots. Boardwalk Empire is basically the story of a twenties gang called The Combined or Big Seven Group. All the biggies on the east coast were part of it and it was multicultural, as crime is. Seven different gangs: Sicilian, Italian, Jewish, and Irish came together to bring people booze during Prohibition. Also, a little bit of smack or something in the sack, they were a very diverse lot. It was the precursor to the National Crime Syndicate of the 1930s.

The Big Seven Group was tired of all the bombings and waste that came in the wake of the Volstead Act when everyone was jockeying for position. They brought down costs and gave general protection and order to the bootleg industry. The Big Seven was Charles “Lucky” Luciano and Meyer Lansky’s operations as well as  Enoch “Nucky” Johnson and Abner “Longy” Zwillman’s outfits from New Jersey, Moe Dalitz from Cleveland, Waxey Gordon and Harry “Nig” Rosen of Philadelphia, Danny Walsh represented for Providence, Rhode Island. Johnny Torrio was a kind of consigliere but Al Capone was too busy dealing with the North Side Gang after he sent Dean O’Banion some flowers, collect. Although he did attend the Atlantic City Conference of 1929, as photos attest, right after Arnold Rothstein died. The Combined was started around 1927, but didn’t solidify until 1928.

So who are these gangsters? These bootleggers? They’re the reasons we tune in to Boardwalk Empire every week and binge watch when it’s not on.

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1. Enoch Thompson (played by Steve Buscemi)

His friends call him Nucky and because he was a career politician, everyone is Nucky’s friend, especially his enemies. Nucky breaks bread with almost all his enemies at least once before he has them done away with. Enoch Thompson is based on Enoch Johnson, a corrupt Atlantic City official. While he does (SPOILER ADVISORY) wind up in jail for a brief period, he lived until the sixties. But Nucky is still a fictional character and Johnson is a jumping off point. Enoch Johnson wasn’t really a gangster, he never shot anyone or ordered anyone shot. He never made his bones, he just took a cut. But he was part of the Big Seven Group. He hosted the powwow for Chicago’s heavy hitters in 1929. Al Capone was there. So was Frankie Rio. (SPOILER ADVISORY) Nucky won’t get busted for the numbers rackets until 1938 and won’t go to jail until 1941. He won’t die until the sixties when he’s 85 years old.

[related article: Boardwalk Empire Close-Up – Enoch “Nucky” Johnson]

2. Al Capone (played by Stephen Graham) 

Capone is most famous for orchestrating the St. Valentine’s Day Massacre and for a scar he got at Frankie Yale’s place that gave him the moniker “Scarface.” Al Capone was born in Brooklyn in 1899. He wasn’t Sicilian, he was Napolitano and because of that, he was never fully accepted into this thing of theirs (va Napoli). He started in the Five Points Gang on the Lower East Side, which was run by Johnny Torrio. Capone was sent to Chicago by Torrio and Frank Yale in 1919 to take the rackets under New York’s wing. He wound up at the top of the Colosimo-Torrio empire in Chicago (SPOILER ADVISORY) when Torrio retired after escaping being retired permanently. Because of Capone, Chicago was pretty much under siege for the second half of the twenties.

Capone tried to take over all of Chicago for himself, not just pissing off the Irish, but also the Sicilians. (SPOILER ADVISORY) Yale put a hit out on Capone over some booze hijacking. Capone had Yale whacked in 1928. Yale was a made man. Capone never got his button so that had to be ironed out at the Atlantic City gang conference. Capone backed Masseria in the Castellammarese War and did the job on Joe Aiello in that war. Wrong side. Luciano backed Mafia father Joe Masseria until, one day, he didn’t and Masseria was found dead in a Coney Island restaurant with an ace of spades in his hand. Capone got sent away for Tax Evasion and died of a stroke after years of being ravaged by syphilis.

[related article: Boardwalk Empire Close-Up – Al Capone]

3. Charles “Lucky” Luciano (played by Vincent Piazza)

Lucky Luciano is best known as the father of organized crime. He started the Five Families in New York and The Commission that oversaw crime in America. He ousted the boss of bosses and, instead of taking the title himself, he followed Johnny Torrio’s advice and created a corporation. Luciano is also known as the mobster who protected the ports of New York and helped the Americans invade Italy during World War II. Charlie Lucky was born Salvatore Lucania in Lercara Friddi, Sicily in 1897. He came to New York when he was ten years old. He had trouble in school until he won almost $250 in a dice game and decided to learn the streets instead. Luciano formed a gang that protected Jewish and Irish kids from Italian gangs for ten cents. Two of the Jewish kids he protected were Meyer Lansky and Benny Siegel. Those three, along with Louis “Lepke” Buchalter, Jacob “Gurrah” Shapiro and Long Zwillman, would be the “Big Six” of bootlegging during prohibition. They were bankrolled by The Big Bankroll himself, Arnold Rothstein.

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Luciano did six months in a reform school for dealing heroin. He was called Lucky because well, he was. He beat 25 prison raps, survived a beating and a throat slashing and not only survived the Castellammarese War, but came out on top. Luciano worked for Joe Masseria but set Masseria up for slaughter by Salvatore Maranzano, who Luciano later had hit. Charlie Lucky took Johnny Torrio’s blueprint for a national organization and put it to work, solidifying the rackets. He went to jail for a little while for running cathouses, made a deal with the government to help them with World War II troubles on the dock and in Sicily and was deported to Naples, where he headed an international heroin ring. He died in 1962.

[related article: Boardwalk Empire Close-Up – Charles “Lucky” Luciano]

4. Meyer Lansky (played by Anatol Yusef) 

Meyer Lansky was saddled with the name Maier Suchowljansky when he was born in Grodno, Russia sometime between 1898 and 1902. When Lansky got to the Lower East Side he made friends with Benjamin Siegel and they started a gang that included Louis “Lepke” Buchalter and got into bootlegging, smuggled drugs and cut themselves in on the labor unions. They met a nice Italian boy from the neighborhood, Charles Luciano, and they made a lot of money.  Lansky did work for Arnold Rothstein and Dutch Schultz. He advised for Joe “the Boss” Masseria. When Luciano started the Commission, Lansky told them what to do with their money.

[related article: Boardwalk Empire Close-Up – Meyer Lansky]

5. Arnold Rothstein (played by Michael Stuhlbarg) 

Rothstein was called “the Brain” because he had a head for figures. Arnold Rothstein, not Meyer Lansky, is the basis for Meyer Wolfsheim in F. Scott Fitzgerald’s The Great Gatsby. He was a nice Jewish kid who went into his father’s business. Rothstein’s father Abraham was also a gangster-businessman. Rothstein was a mob boss in New York and is best known for fixing (though he was never convicted) the World Series in the “Black Sox Scandal” of 1919, the year that the Volstead Act was passed. He also fixed the 1921 Travers Stakes horse race.

Rothstein started casinos in Manhattan, distributed drugs and was a bootlegger who also ran speakeasies. The Brain also had an eye for talent, as well as seeing the potential in Luciano and Lansky, he used Jack “Legs” Diamond and Dutch Schultz on jobs. Rothstein’s headquarters was Lindy’s, a restaurant on 49th Street. Besides Owney Madden, he’s my favorite early non-Italian mob boss. Though I love John Dillinger, he only headed a gang. The Brain cleaned up the mobs and turned them into a business. He made himself the CEO, of course. (SPOILER ADVISORY) When Rothstein was offed by some fucking hump for welching on a poker bet in 1928 his corporation was busted out and spread among the other mobs. Rothstein died in police custody. He knew who killed him, but he never ratted. When the cops asked him who shot him, Rothstein answered “Me mudder did it.”

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[related article: Boardwalk Empire Close-Up – Arnold Rothstein]

6. Johnny Torrio (played by Greg Antonacci) 

Johnny Torrio is best known for being Al Capone’s boss, but he is the real architect of the syndicate. Giovanni Torrio was born near Naples in 1882. He came to New York when he was two. He operated a saloon-whorehouse and brought the James Street Boys together with the Five Points Gang. Torrio strong-armed his way to the top of the rackets and then was sent to Chicago in 1909 to expand “Big Jim” Colosimo’s cathouses. He called New York for some help and Frankie Yale sent Al Capone out to Chicago in 1919 to run one of the brothels. When someone, Frankie Yale, I’m looking at you, whacked Colosimo, Torrio took over Chicago and supplied all the usual vices.

As a bootlegger, Torrio profited from The Combine, through his connection to Charlie Lucky and Meyer Lanksy. Torrio ran Chicago until the mid-twenties when someone took a couple pops at him and he did nine months in prison. When he got out, he retired to Italy leaving Chicago in the hands of Al Capone and Frankie Rio, who went to war with everyone else in town. Torrio only retired for about three years. He went back to America in 1928 and in 1934 advised Luciano on the creation of the syndicate. Torrio sat on the Commission. He went back to jail for tax evasion for two years, 1939-1941 (spanning two decades, as Mickey Rooney would say in The Simpsons) retired again and died in a barber chair in 1957. Not to be confused with Albert “The Lord High Executioner” Anastasia who was the victim of the “Barbershop Quintet” in December 1957.

[related article: Boardwalk Empire Close-Up – Johnny Torrio]

7. Mickey Doyle (played by Paul Sparks) 

Mickey Doyle is based on Mickey Duffy, who was based on William Michael Cusick, one of the Polish gangsters from Philadelphia and yeah, he was stupid enough to change his name to try to fit in with the Irish gangs. Duffy was a thief and a hijacker who went to prison eight times. He got popped for assault with intent to kill and did almost three years for it starting in 1919. When he got out, prohibition was in swing and Duffy danced, setting up breweries throughout Philly and South Jersey.

Duffy battled it out with other area bootleggers and expanded into numbers rackets and legitimate clubs. In the first Tommy gun shooting in Philadelphia, Francis Bailey and Peter Ford caught Duffy coming out of one his nightclubs, the Club Cadix, on Feb. 25, 1927 and shot him. They killed his bodyguard and put a hole in the club’s doorman. Duffy muscled into Northern New Jersey and stepped on Max Hassel’s toes. Hassel was an associate of Waxey Gordon. Duffy got heat after a Prohibition agent was killed in a raid at one of his breweries in Elizabeth, N.J. Duffy was killed at the Ambassador Hotel in Atlantic City in what looks like a power grab on Aug. 31, 1931. The guys that shot Duffy, Samuel E. Grossman and Albert Skale, were hit two months later starting a mob war in Philadelphia. Thousands came to see Duffy off, but cops only allowed the family and some friends to attend the funeral.

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[related article: Boardwalk Empire Close-Up – Mickey Duffy]

8. Benny Siegel (played by Michael Zegen).

Benny Siegel is best known as “Bugsy” and was known to go off on people if they called him that to his face. He is also remembered as the mobster who invented Las Vegas. Benjamin Siegel was an associate with the Luciano family. He made his bones on the Lower East Side. Siegel and Meyer Lansky met when they were teenagers and organized themselves as the Bugs and Meyer Gang which included Louis Buchalter, better known as “Lepke,” Lepke and Bugsy started Murder, Incorporated. Siegel ratted Waxey Gordon out to the feds because he wasn’t paying his taxes. Siegel was one of the shooters on the Joe Masseria and Salvatore Maranzano hits. Benny Siegel made friends with celebrities and almost married a celebrity. He was the mob’s face on the left coast until they messed up that face by shooting out one of his eyes (a Moe Greene special), an old Sicilian message or a very lucky shot. One thing Boardwalk Empire hasn’t mentioned about Siegel and Al Capone (Stephen Graham): The two were friends since they were kids. Capone hid out at Siegel’s aunt house when he was ducking a murder rap.

[related article: Boardwalk Empire Close-Up – Bugsy Siegel]

9. Dean O’Banion (played by Arron Shiver) 

Charles Dean O’Banion is best known as the guy who was taken out by Johnny Torrio and Al Capone. Newspapers at the time called him Dion O’Banion and as a kid he was called “Gimpy” behind his back because a streetcar left one of legs shorter than the other. O’Banion came up through the Market Street Gang. O’Banion, Earl “Hymie” Weiss, Vincent “The Schemer” Drucci, and George “Bugs” Moran hired themselves out to newspapers as “sluggers” to strong arm newsstand owners. O’Banion majored in safecracking under Charles “The Ox” Reiser. He started the North Side Gang during prohibition and made about $1 million a year hijacking booze.

O’Banion bought an interest in William Schofield’s River North flower shop in 1921 as a cover. Schofield was the go-to florist for mob funerals. After tough negotiations, O’Banion gave Johnny Torrio and his lieutenant, Al Capone the North Side of Chicago in 1920, but wanted it back three years later. To avoid a bootleg war Torrio tried to trade some of his brothels, but O’Banion was no pimp and got angry. O’Banion asked for Torrio’s help with the Genna Brothers from Chicago’s Little Italy. They were Sicilian, not Italian and O’Banion only lived through that because the Unione Siciliana wouldn’t sanction a hit. When O’Banion double-crossed Torrio on a brewery deal in 1924, things took a downward spiral. Torrio and Angelo Genna sent Genna’s gunmen John Scalise and Albert Anselmi and Frankie Yale to do the hit on O’Banion on November 10, 1924. It started a gang war that lasted five years, but O’Banion got a huge mob funeral.

[related article: Boardwalk Empire Close-Up – Dean O’Banion]

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10. Joe Masseria (played by Ivo Nandi) 

Giuseppe Masseria was best known as “Joe the Boss.” He was also known as “the man who can dodge bullets” because he survived a multi-gun execution attempt on Bowery. The hit crew wounded six people, killed two people and a horse and shot Masseria at point blank range. Masseria had bullet holes in his hat and ringing in his ears. Masseria was the father of what is now the Genovese family, which was called the Luciano family before he got deported. Masseria was born in Marsala, Sicily and came to America to escape a murder rap. With the backing of Salvatore D’Aquila, whose family would become the Gambinos, Masseria was named capo consigliere of the early New York mob families after Nick Morello died.

Masseria never actually held the title “Capo di Tutti Capi,” but did head the Morello family after an ambush took out Umberto Valenti. Word on the street is Charlie Lucky did the job on Valenti.  After Frankie Yale died in 1928, Joe Masseria wanted to be the boss of bosses. The only thing standing in his way was “Little Augie” Pisano, who was the don of the Yale family. After a little finagling, Masseria became “Joe the Boss” of his own Sicilian family. He wanted to dip his beak into “the Broadway Mob” and siphoned “Lucky” Luciano because he was the only Sicilian in a group of Italians and Jews. Luciano balked at first, but after realizing that his Sicilian heritage afforded him more perks, he paid tribute and bided his time. Masseria started the Castellamarese War when he asked for Salvatore Maranzano’s head on a platter. He got served up himself instead. Legend has it that he was fingered by Luciano and shot by Benjamin “Bugsy” Siegel, Vito Genovese, Albert Anastasia, and Joe Adonis and that he died with the ace of spades in his hand, but there were actually only two shooters who hit him with 20 shots and left the guns in the alley. They took the canoli.

[related article: Boardwalk Empire Close-Up – Joe Masseria]

11. Waxey Gordon (played by Nick Sandow) 

Irving “Waxey Gordon” Wexler was known, as a kid, for being such a good pickpocket that it was like people’s wallets were lined with wax. Waxey Gordon came up through Dopey” Benny Fein’s labor sluggers. Waxey ran rum and gambling houses for Arnold Rothstein and was so good at it The Brain put him in charge of all his bootlegging operations and he pulled in about $2 million a year for himself. Waxey Gordon lived large, buying mansions and living in New York City’s finest hotels, but kept his family out of the loop. When Rothstein died, Waxey aligned himself with Charles Luciano and Meyer Lansky until Lansky got sick of him and Luciano fed him to the feds for tax evasion in 1933.

When Waxey got out ten years later, his gang was gone and his political connections dried up. He got divorced and moved west to be Irving Wexler, sugar salesman. It wasn’t sweet enough and he got popped for peddling smack. He tried to bribe his way out of it, but died in Alcatraz in 1952.

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12. Big Jim Colosimo (played by Frank Crudele) 

Vincenzo “Big Jim” Colosimo is best known as the guy who was permanently sidelined so Johnny Torrio and Al Capone could take over Chicago for New York. Colosimo was born in Calabria, Italy. He ran cathouses and social clubs in Chicago and got into the gambling rackets when the Black Hand came down on him asking for a taste. Colosimo called Torrio and Frankie Yale for help. Torrio moved to Chicago in 1909 and broke the Black Hand’s fingers. When Torrio found out Al Capone needed to get out of New York to dodge a murder rap in 1919, Torrio told Colosimo to take him on.

Colosimo was slow to move into bootlegging, so Torrio and Capone called Frankie Yale in to get him up to speed and Colosimo was hit on May 11, 1920. Whether it was by Frankie Yale, the Mafia, represented by the Genna and Aiello families (Torrio and Capone were not Mafia), or Colosimo’s in-laws is not really known.

13. George Remus (played by Glenn Fleshler) 

George Remus is best known for inspiring the character Jay Gatsby in F. Scott Fitzgerald’s The Great Gatsby. He was also known as the King of the Bootleggers. George Remus had a daughter named Romola Remus who played Dorothy Gale in the 1908 silent version of The Wizard of Oz. Remus was born in Germany and moved to Chicago when he was five. When he was 14, he worked at a drugstore to support his family. When he was 19 he bought it. Then he bought more drug stores. George Remus got sick of drug stores, and his wife, and became a mouthpiece and married his secretary, Imogene. Remus became a criminal defense lawyer, specializing in murder and was pulling in $500,000 a year by 1920.

When the Volstead Act was passed Remus memorized it and found enough loopholes to pull in $40 million in three years. George Remus threw parties. He gave kids money to buy clothes. He gave guests diamond watches. He gave their wives new cars. In 1925, the Feds read their own Volstead act and realized Remus violated it thousands of times. It took a jury two hours to give him two years. While he was in prison George Remus made friends with an undercover fed who quit his job and slept with Remus’ wife. Imogene liquidated and hid George Remus’ assets. After a day in divorce court, Remus chased Imogene’s car and shot her to death in front of a park full of people. Remus defended himself with claims of insanity. The jury thought he was crazy and sentenced him to six months in an asylum. When Remus got out, he retired from bootlegging and died quietly in 1952 of natural causes at age 77.

[related article: Boardwalk Empire Close-Up – George Remus]

14. Frankie Yale (played by Joseph Riccobene) 

Frankie Yale, was called the “Beau Brummell of Brooklyn” and the “Prince of Pals” because he was quick with a joke and helped out a lot of people in the neighborhood. Frankie Yale and Capone came up through the Five Points Gang, and their Dutch uncle was Johnny Torrio. Yale owned The Harvard Inn, where Frank Galluccio slashed Al Capone across the face and Capone got the nickname “Scarface.” Yale is the guy who sent Capone to Chicago to work under Johnny Torrio. He was one of the biggest bootleggers in Brooklyn. Future bosses Albert Anastasia and Joe Adonis worked under him. In 1920, Yale took out Jim Colosimo so Torrio could take over Chicago. (SPOILER ADVISORY) Yale, along with John Scalise, and Albert Anselmi, did the hit on Dean O’Banion for Torrio. Yale survived four attempted hits. One on the orders of Capone. Yale was also the first mobster to be taken out with a tommy gun. Yale’s funeral was one of the biggest in mob history. Two women showed up at Holy Cross Cemetery who said they were his wife.

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[related article: Boardwalk Empire: Frankie Yale Close-Up]

15. Hymie Weiss (played by Will Janowitz) 

Henry Earl J. Wojciechowski was known as Hymie Weiss or Hymie the Pole. He was also known as “The Perfume Burglar” because he spilled perfume during a robbery. Weiss worked for Dean O’Banion in the North Side Gang. Weiss intimidated everybody. He threatened to kill photographers if they took his picture. His brother said he saw Weiss once in twenty years “when he shot me.” When a party Weiss went to was raided for Mann Act violations, Weiss sued to get his silk shirts and socks back. Weiss was killed on October 11, 1926 outside of O’Banion’s Schofield flower shop. He is buried at the same cemetery as Al Capone and Dean O’Banion, Mount Carmel Cemetery in Hillside, Illinois.

16. – 20. – The D’Allessio Brothers are The Lanzetti Brothers.

Eric Schneider plays Sixtus D’Alessio; Max Casella plays Leo D’Alessio, Nicholas Alexander Martino plays Pius D’Alessio and Al Linea plays Matteo D’Allesio. The D’Allesio Brothers are based on the six Lanzetti brothers, four of whom were named after popes. Pius, Ignatius, Lucien, Teo, Leo, and Willie Lanzetti controlled the Little Italy section of South Philadelphia’s prostitution, bootlegging, numbers and dope rackets.

The press loved them because they died well. Willie Lanzetti’s corpse was found beheaded and his head was found in a burlap bag with a bullet in the brain. Leo was shot in South Philadelphia in 1925; Pius got it in a luncheonette (what part of the body is a luncheonette?) on Dec. 31, 1936. Willie’s corpse was found in two sewn-together potato sacks on the Wynnewood Estate on July 31, 1939. Ignatius Lanzetta, their real name according to a Supreme Court Case, got a law changed. He was convicted, basically, of being a gangster and because he was a gangster there was a minimum sentence. There was no crime actually named, just that he was a gangster. The Supreme Court said that sounded repugnant under the Fourth Amendment.

21. Salvatore Maranzano (played by Giampiero Judica) 

Salvatore Maranzano, also known as Don Turridru, was born on July 31, 1886, in Castellammare del Golfo, Sicily. Maranzano was a Sicilian hero and had studied to become a priest. On orders of Sicilian mob family father Don Vito Cascio Ferro, he emigrated to Brooklyn, USA, in 1919. His legit business was as a real estate broker, but he made his scratch with booze, prostitution and drugs.

Maranzano had a fascination with Julius Caesar and based his crime structure on the military of the Roman Empire. Maranzano divided his army into squads and each soldier had to pledge loyalty to his squad leader. Maranzano instigated the Castellammarese War in 1930, when he went up Joe Masseria. On April, 15, 1931, Masseria was set up for execution by Charles “Lucky” Luciano on Maranzano’s orders. Word on the street is Benjamin “Bugsy” Siegel and Albert Anastasia did the deed. Winning the Castallammarsese War, Maranzano made Luciano his number one man, set up the Five Families, and declared himself “capo di tutti capi.”  

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Fearing Luciano’s growing power, Maranzano contracted Mad Dog Coll to murder Luciano, but Lucky acted first. Lucky Luciano and Vito Genovese contracted Samuel “Red” Levine and three other gangsters who worked for Meyer Lansky to do the job on Maranzano. Posing as tax officers, they hit Maranaon in his  office in Grand Central. On Sept. 10, 1931, they shot and stabbed Salvatore Maranzano to death. In his autobiography, A Man of Honor, Joseph Bonanno says he didn’t know about the plot to kill Maranzano. Bonanno became the youngest crime boss in America at the age of 26. The Maranzano family became known as the Bonanno family.