By Matt Goldstein
1. Al Capone:
One of the first nationally recognized gangsters and the most legendary bootleg booze smuggler in history, Al Capone was extremely wealthy and a brutal murderer. At one point in the 1920’s Capone was allegedly pulling in more than $60 million a year off of booze alone and another $40 million in racketeering, prostitution and gambling. After the rival Bugs Moran gang over stepped their bounds by stealing one too many of Capone’s booze shipments, Capone’s henchman dressed up as police officers and faked a raid on the Moran warehouse. The disguised enforcers lined up 7 members of the Moran gang against the wall and executed them. This incident became known as the St. Valentine’s Day Massacre. Capone was never convicted of illegal smuggling but couldn’t hide all of his money from the IRS. In HBO’s Boardwalk Empire, Capone is portrayed as a young henchmen who orchestrates a robbery of a shipment of booze owned by Arnold Rothstein.
Perhaps the richest gangster in the history of the world, Lucky Luciano and partner Meyer Lansky made more money than any mobsters ever without even accounting for inflation. Most of this money was probably made by heroin long after prohibition had ended. However, Luciano is credited for making the peace with fellow gangsters in an attempt to quell the violence and save money on shipments and political bribes. Associated with the National Crime Syndicate, head of the Commission and the Young Turks, Luciano brought all the heavyweight gangsters together, including Al Capone. Luciano was one of the first Italian gangsters to align himself with Jewish mobsters such as Allan Rothstein, Meyer Lansky and Ben Segal, as well as Italian gangsters Frank Costello, Vito Genovese, Johnny Torrio, Joseph Bonano and Al Capone. These guys were the champions of bootlegging. In Boardwalk Empire, Luciano is portrayed as a hot headed young associate of Rothstein.
3. Meyer Lansky:
Legend has it that it was Lansky’s idea to create the Commission but some say it was Johnny Torrio that convinced Luciano that the Commission was the right thing to do. Yup, it was a Jew’s idea that all of the leaders of the Italian mob sit down and work together for better business and the benefit of everyone. Maybe Henry Ford was right about the International Jewish Conspiracy to control all the money. After all, I still get my Jew check in the mail every week. Again, perhaps the richest gangster in history with his close friend and associate Lucky Luciano, Lansky was instrumental in Luciano’s rise to power and the creation of the Commission. Lansky’s gambling business stretched from New York, to Florida, Cuba and Vegas. In the 30’s and 40’s, Lansky actually worked with the U.S. government in providing security for naval ships in the port and intimidating Nazi sympathizers.
Leader of the Chicago outfit and mentor of Al Capone, Torrio is credited for creating the bootlegging empire that Capone would takeover and expand. Torrio was also heavily influential in creating the Commission with Luciano and Lansky and a close ally of the Genovese family. At the beginning of Prohibition, Torrio’s boss, Jim Colosimo, refused to smuggle booze figuring it would bring too much heat from the Feds. Torrio had Colosimo murdered in his own restaurant, as portrayed on HBO’s Boardwalk Empire at the end of episode 1. This assassination opened the flood gates for Torrio and Capone to become bootlegging legends.
5. Arnold Rothstein:
Allegedly fixing the 1919 World Series by paying Chicago White Sox players to intentionally lose to the Cincinnati Reds, Rothstein was also one of the first gangsters to set up major bootlegging operations during the onset of Prohibition. Rothstein advised many crime families and attempted to take the violence out of the business. Rothstein was also a legendary gambler but was murdered in 1928 after reneging on a $300,000 loss in a poker game. Refusing to pay after accusing the other players of cheating, Rothstein murderers reportedly killed him in order to teach Rothstein a lesson. On his deathbed, the Jewish Rothstein stuck to the code of the streets and refused to name his assassins. In episode 1 of HBO’s Boardwalk Empire, Rothstein is portrayed as a gambling cheat and slick deal maker only to have a shipment a booze stolen.
6. Bugs Moran:
Chief rival and arch enemy of Johnny Torrio and Al Capone, the Polish and Irish Moran was never took orders from the Chicago Outfit and Southside Gang. In fact, Moran stole Torrio and Capone’s booze at will. Aligning himself with the Irish bootlegger Dean O’Banion, Moran’s outfit became known as the Northside gang. Throughout the 20’s, the Chicago Outfit and Southside Gang battled the Northside gang in shootouts, kidnappings, murder and torture. After O’Banion’s assassination at the hands of Capone and Torrio, Moran continued to battle Capone for years. The exclamation point on the war was the eventual St. Valentine’s day massacre when seven of Moran’s men were executed. However, Moran never wavered, controlling most of his territory and taking revenge by murdering Capone associates for almost a decade to come.
Originally a sheriff in Atlantic City, Nucky rose to power as one of the leading Republican political figures. Nucky used his political influence to establish Atlantic City as one of the leading ports for bootlegging and allied with Rothstein, Luciano, Torrio, Capone and others. Johnson is actually portrayed as Nucky Thompson as the main character of HBO’s Boardwalk Empire and played by Steve Buscemi as a charitable, level headed and charismatic business man in episode 1.
8. Frank Nitti:
Dubbed the “Enforcer,” Nitti was the go to muscle for anyone that didn’t fall in line with Capone’s wishes. Nitti also ran Capone’s smuggling operations and later became the front man of the Chicago Outfit.
9. Bugsy Segal:
An enforcer for Lansky since they were teenagers, Segal became a mob hitman for multiple families during Prohibition. Segal aligned himself with Lansky, Luciano and Frank Costello and established bootlegging operations with close ally Albert Anastasia. Known by many as the father of Las Vegas, Segal was murdered in 1947 after the financing of the Flamingo Hotel seemed to disappear.
10. Vito Genovese
11. Frank Costello
12. Albert Anastasia
13. Joseph Bonano
14. Tommy Luchese
15. Carlo Gambino