The 5 Most Bro Gangsters of All Time

5. Salvatore Marazano

Maranzano was like your buddy who always dressed better than you, and knew how to pull out the high-brow literary axioms to impress the ladies while you’re quoting Caddyshack and Spaceballs. This blue-blood, University-educated Mafioso was brought to NYC from Sicily in the 1920’s to stop fat and greedy Joe Masseria’s power grab over New York City. He was smart, cunning, cautious and debonair, quoting political philosophers with such gems as: “Man is the most challenging game to hunt. He is the only beast that if you shoot and miss… he comes back to shoot you.” Marazano helped modernize the Mafia by incorporating the Five Families of New York, installing himself as Il Capo di Tutti Capi: The Boss of All Bosses.

Less that a year later he was stabbed to death in his midtown office by four hitmen dressed as U.S. Treasury agents. Lived like a mobster, died like a businessman: bled dry by the IRS.

4. Benjamin “Bugsy” Siegel

You know the bro that your girlfriend never wants you to hang out with because he always gets you in trouble, and she’s the one who has to scrape up the bail money? That was Bugsy. Sipping champagne with Hollywood movie stars one minute and mashing some mook’s face through a telephone booth the next, Bugsy was an enigma. He caught the nickname when he was a kid because, they said, “It was as if he had bugs in his head.” He was so unpredictable that The Mob sent him away from New York to organize the L.A. rackets, which they assumed would be a pushover. They were right.

In the post-war boom of the late 1940’s, he had a vision of a hotel casino nightclub in a small desert town called “Las Vegas” where gambling was legal. Building it cost six times what he quoted his partners and on the big opening night in 1948, it was raining. In the desert. His big Las Vegas project was written off as a failure and he was riddled with 15 bullets not long after.

3. Charles “Lucky” Luciano

Lucky was the kind of guy who would always pick up the bar tab… only to remember that you owed him a favor at just the right moment. One of the greatest illegal businessmen of all time, Charles Luciano was a forward-thinking mobster and a true visionary in recognizing the lucrative power of heroin before anyone else. He also had the radical notion of breaking away from the Sicilian Mafia, and doing business with the Irish and the Jews, as well as turning the American Crime Syndicate into its own corporate organization.

His true stroke of grace was to help the American government during WWII by protecting merchant ships from Nazi sabatouers and assisting with the American invasion of Sicily—which overthrew Benito Mousolini—all in exchange for a shorter prison sentence. His 30-year stretch was shortened to 10, and he was deported to Sicily only a week after being granted freedom.

2. Paul Kelly

Paul Kelly was that friend of yours who could run with both the theater geeks and the hard-drinking, bar-fighting crowd. The last of the non-Mafioso Italian Gang Bosses of NYC, Kelly changed his name from Paolo Vaccharelli to reflect the turn-of-the-20th-century’s dismissal and mistrust of Italians. Looking upon him, one might think him a star of the Bowery show houses, quoting Shakespeare and Poe from memory—until you put him in a boxing right and watch him take down a man twice his size with a few well-placed blows.

He was the final leader of the notorious Five Points gangs and nearly tore the city apart in 1903 over a summertime battle with the Eastman gang for control of the card racket on the Lower East Side. A year later, he barely escaped two attempts on his life and smartly decided that it might be time to leave town.

1. Frank Costello

What’s one of the most important aspects of a proper bro? Like the peak of Ron Swanson’s pyramid of greatness: Honor. Frank Costello was the acting chairman of the Mafia syndicate during Luciano’s time in exile, when the Mob syndicate decided to start up the greatest heroin smuggling operation in world history. Costello was the strongest voice in opposition, famously declaring “Drugs are a very dirty business. Our political friends might not stay our friends for long if we involve ourselves in such a thing.” This quote was paraphrased by Vito Corleone in Godfather Part I, for whom Costello was the primary inspiration.

A gunman just barely missed taking off Costello’s head in a botched hit in 1957 for daring to oppose such a lucrative opportunity. Costello wisely chose to retire shortly thereafter, wanting no part in the way the Mafia was headed.