Arnold Rothstein’s 7 Habits of Highly Successful Gangsters

Gentleman gangster Arnold Rothstein did it his way on Boardwalk Empire. Based on a real-life macher, he was the kind of guy who preferred milk to whiskey in an Atlantic City swimming in Canadian Club; the sort of man who’d fix the 1919 World Series — and get away with it. Cold, calculating and deadpan hilarious, he’s one of actor Michael Stuhlbarg’s most quotable creations in a career that’s grown to include a trio of acclaimed turns in 2017 (Call Me by Your Name, The Post and The Shape of Water).

Here, a few lessons from the man who ruled the Jazz Age, according to the man himself. Aspiring gangsters — take note. (Possible spoilers ahead.)


Understand the power of information.

Episode: The Emerald City (Season 1, Episode 10)

“It’s the age of information, and the businessman lives and sometimes dies on its value,” Arnold Rothstein lectures an audience of goons in Season 1, summing up his forward-thinking approach to malfeasance: “I create my luck. I’m a successful gambler because I never bet on an event I’m not sure of in advance.”   


Punctuate your point.

Episode: The Ivory Tower (Season 1, Episode 2) 

Beneath the calm composure of Arnold Rothstein, there were chilling depths — as mob enforcer Frankie Yale discovers when the racketeer tells a story about billiard balls and someone who underestimated his intelligence.

“The moral of this story?” Rothstein concludes, leaning over his pool cue. “If I’d cause a stranger to choke to death for my own amusement, what do you think I’ll do to you…?


Learn how to make difficult decisions.

Episode: To the Lost (Season 2, Episode 12)

A criminal mastermind who blurred the line between gangster and businessman, Rothstein was also an astute observer of human psychology. Sharing friendly advice with Nucky who has come for help deciding a man’s fate, Rothstein advises:

“Flip a coin. When it’s in the air, you’ll know which side you’re hoping for.”


Don’t be afraid to risk everything.

Episode: Two Boats and a Lifeguard (Season 2, Episode 8)

What does a successful businessman and gangster have in common? A willingness to gamble. What do they often lack? Patience. Arnold Rothstein is a high-roller with superhuman impulse control

“Some days I make 20 bets, some days I make none,” he instructs Nucky Thompson. “So I wait. Plan. Marshall my resources. And when I see an opportunity, and there is a bet to make... I bet it all."


Don’t hold back your anger.

Episode: You’d Be Surprised (Season 3, Episode 5) 

Arnold Rothstein maintained a calm front, but when Nucky Thompson suggests waging war with live wire Gyp Rosetti (Bobby Cannavale), it triggers Rothstein to go for the jugular. And for very Rothstein-reasons.

“Owing to your inability to manage your own affairs in New Jersey … you expect me to start a war in New York?” he thunders. “Where things actually matter?”


Know the value of a real apology.

Episode: The Emerald City (Season 1, Episode 10)

Imagine you’ve let down one of America’s most notorious gangsters, bungling a hit on Atlantic City powerhouse Nucky Thompson (Steve Buscemi). Better get on your knees and beg, right? Yes, but Arnold Rothstein is an enlightened hood.

“Nothing says ‘I’m sorry’ like money,” Rothstein tells the repentant D’Alessio brothers. It’s a line that could serve as his Boardwalk credo.


Cover yourself from all sides.

Episode: A Return to Normalcy (Season 1, Episode 12)

Like a master chess player, Arnold Rothstein protected himself from every angle. In the climax of Season 1, Rothstein sacrifices $1 million and the D’Alessio brothers to Nucky in exchange for legal protection. Little did Nucky know that the D'Alessios all had life insurance policies — with Rothstein listed as the beneficiary.

“We could wage war for years. It benefits no one,” Rothstein concedes to Nucky, while in reality, he’s holding all the cards.