Jonathan C. Stewart, actor who plays Benjamin "Bugsy" Siegel in the new AMC series,The Making of the Mob (Photo: Nicole Disser)

Jonathan C. Stewart, actor who plays Benjamin “Bugsy” Siegel in the new AMC series,The Making of the Mob (Photo: Nicole Disser)

We couldn’t have picked a better spot to meet Jonathan C. Stewart, the actor who plays notorious mobster Benjamin “Bugsy” Siegel on AMC’s new show, The Making of the Mob. The Williamsburg dive bar, Jr. & Son is located in the neighborhood where Bugsy was born and raised, but in a way it’s hard not to find in the place a spiritual home for Brooklyn mobster lore as well. A grumpy looking bartender sporting a gold chain, thin mustache, and what was left of his hair slicked back grumbled to his regulars in a naturally aggressive Brooklyn wise-guy intonation. “Huh, lifestyles of the rich and famous, eh?” he said gesturing with disdain towards the TV in the corner. The sun was still shining outside, but inside it felt like a rainy day.
Stewart is a genial Midwestern dude with an easy smile. Even with the help of a fedora, I had to squint hard to imagine him harnessing the violent energy to play a personality like Bugsy Siegel, a hot-headed mobster who had about as much blood on his hands as he had style.

“You’re body is so engaged with the weight of a gun or sacking someone with a lead pipe when you’re acting with those props, so you don’t really have to think too much, you can kind of just let it go,” Stewart explained. I noticed a couple of the regulars shift in their seats. “Until I was about 23, I had a really quick temper. I moved beyond that, but I was able to tap back into that.”

And it’s a good thing Stewart was able to channel this former predilection, because Bugsy might be one of the most violent characters in The Making of the Mob. The show traces a few well-known mobsters whose histories intertwine from the beginnings of the Italian and Jewish mob syndicates in turn-of-the-century New York City. Figures like Bugsy and his partner in crime Meyer Lansky, as well as Sicilian mafia figures like Charles “Lucky” Luciano, are at the center. Many of these guys had an impressive rise often followed by dramatic ends, starting out as petty street criminals who moved on to racketeering and eventually became major crime bosses with a reach that spread from New York City to Las Vegas and everywhere in between.

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Bugsy Siegel’s name might not elicit instant recall unless maybe you’re a huge organized crime nerd, but he was actually an extremely powerful mob figure in his day, as one of the central figures in a group the press dubbed Murder, Incorporated. Siegel is also considered a sort of Founding Father of the Las Vegas strip.

Stewart initially tried out for the part of Dutch Schultz, another important Jewish mobster who was offed for his disobedience before he turned 40. Following the audition, Stewart found he’d instead scored the roll of Siegel. He accepted the roll, thankful that he’d get more screen time, though Stewart admits he first had to check up on who the guy was. “Through the research process I was able to learn a lot about what the mob was,” Stewart explained. “It was like going to history class.”

Stewart was fascinated by the dramatic rise and fall of Siegel in particular. “Early on, it was brutal and street-gangish, but when they got into their later years, they were really running it as a business — they were involved in a lot of different places,” Stewart explained. “They were in Italy, Puerto Rico, and it was really a part of governance. Even when they were sent to jail, there were ways they could get out because they could help out the American Government with something in Italy, for example.”

Though The Mob doesn’t shy away from violence and mobster glitz (iconic mafioso actor Ray Liotta narrates the show), it’s not all drama. “What’s really neat about this show is that it’s historically accurate,” Stewart explained.

AMC is calling the show a “docu-drama,” as it includes archival footage, interviews with historians, family members and confidantes of the mobsters, including famed mafia attorney and former mayor of Las Vegas Oscar Goodman. For some reason, the creators also thought it wise to consult Mayor Rudy Giuliani aka Ol’ Crazy Mouth. We can’t wait to see what comes out of the old dude’s spittin’ hole for this one.

Benjamin Siegel was born in Williamsburg, Brooklyn in 1906 to Russian Jewish immigrants. Growing up poor, his parents always struggled to make ends meet. As a kid, he joined a street gang on the Lower East Side. When Siegel was a teenager Italians were running the criminal underworld, and a friend of his, Meyer Lansky (who would later on became one of the top mobsters in the US), decided that Brooklyn Jews should team up and create their own crime network in kind.

Benjamin "Bugsy Siegel" in a mugshot taken by the NYPD in 1928

Benjamin “Bugsy Siegel” in a mugshot taken by the NYPD in 1928

“So I’m Irish Catholic, I don’t know quite what it was to be a Jew in the early 20th century,” Stewart admitted. “But I take great pride in who I am, and at that time the Italian mobsters, they didn’t want to work with Jewish people, but Bugsy was really proud of who he was, and I think that fueled his fire.”

And “fire” is a pretty apt word to describe Siegel, a notorious hothead. His nickname, which means crazy (i.e. bugging out or “crazy as a bedbug“) was a pretty clear indicator of his reputation as a murderer, one that was solidified even before he was an adult.

“He was a super sociable guy who had a violent temper,” Stewart explained. “He took pride in the fact that’s what he was known for, flipping the switch and going nuts.”

Bugsy was also a charmer, a wolf in a slick suit. “He was always such a snazzy dresser,” Stewart said. True to AMC’s style (see Mad Men) the costumes play a significant part in setting the scenery in The Mob from the Prohibition-era on through the 1950s. “The clothing part was really cool — the suits, the way they fit, it’s almost like a corset, everything’s tight,” Stewart said, explaining that a big part of developing his character happened once he was suited up. “And they’ve got those hats, and the way they smoke cigarettes, and walk around, it’s all different — it really was peacockish.”

“This guy had all of New York under wraps,” Stewart said. But by 1931, Bugsy and Meyer had propelled their underworld reach from New York City to the West Coast. “Prohibition was where it really popped off,” Stewart explained. “Everyone wanted to drink and the mobsters were like, well we don’t care.”

Bugsy and his cohorts became bootleggers, smuggling alcohol across the border from Canada and setting up various distribution chains across the Eastern Seaboard. Meanwhile, the law started to catch up with Bugsy and various charges were brought against him. Though one by one, each case was dismissed.

Meyer Lansky in 1958

Meyer Lansky in 1958

If Bugsy appeared to be above the law, he was becoming an increasingly wanted man amongst rival crime families. Eventually, his associates believed Bugsy’s life might be in danger. As a means of dodging the hits taken out against him, Bugsy’s associates moved him out to California. He made a big splash in Hollywood. Movie stars were either fascinated by Bugsy’s reputation or too afraid not to invite him to all the parties.

“He could go and mingle in these Hollywood circles with like, Cary Grant, and be on the front page, and people just thought he was cool,” Stewart explained. As an actor, Stewart identified with Bugsy’s love of attention. “I love to be in the spotlight, I love curtain calls, everything. Bugsy also liked to be involved, he didn’t like to be forgotten, and he really enjoyed people knowing that he’d killed people before. He liked being flashy and feared at the same time.”

In 1941, a killing that took place a couple of years prior finally caught up with Bugsy, and he was tried for murder. Though in many ways, Siegel was relieved of the inconveniences suffered by most accused criminals, (he received preferential treatment in jail – think Goodfellas) and one by one, the prosecution’s star witnesses were murdered. Eventually, the case was dismissed for lack of evidence. But it was too late for Bugsy’s reputation in the public eye – the press coverage was sensational and even after he was acquitted, Bugsy Siegel became a household name synonymous with organized crime and murder.

In 1945, in an effort to go legit, Siegel invested in the construction of the Flamingo Hotel & Casino, which would become a city landmark on the strip. “When he was pretty much building Vegas, he was getting completely duped by contractors and stuff, so by the end of it all, he and the Flamingo were massively in debt,” Stewart explained. “That was a tough break for him. He was a visionary, and very ambitious, I just think he got in a little over his head.”

After a nearly disastrous start, it took years for Bugsy to make the Flamingo profitable. And just when things started to be looking up for Siegel, it all fell apart and in 1947 he was shot to death in a Beverly Hill’s home where he was staying by what the Times described as “a fusillade of bullets.” In the end, despite decades of close friendship with Siegel, Meyer Lansky helped organize Bugsy’s murder.

The Flamingo Hotel & Casino in 1945

The Flamingo Hotel & Casino in 1945

Despite Bugsy’s use of violent means to an end and his constant thwarting of justice, Stewart was still impressed by the mobster’s achievements. “Sure, you can see a lot of these guys, especially Bugsy, as really brutal, sociopathic people I guess, but they were just making the best of what they had,” he said. “It’s crazy to think of how far these guys traveled with no education, none of them went to school, but they weren’t stupid. Considering all the things they didn’t have, it was really remarkable to see how far they made it through the world.”

We spoke about how, for a long time, there’s been this mythology of America as the land of equal opportunity. But the reality is that class mobility isn’t so easy as the American Dream would have it. People like Bugsy Siegel started out with the odds stacked against them, and though violence is never justifiable, Bugsy and the other gangsters worked with what they had and made remarkable things happen out of thin air. “They saw it as they just had to do it this way, there weren’t really many other options for them,” Stewart said. Although we both agreed, “To get away with something is much harder now than it was then – today, these guys would be like, done.”

We wrapped up the interview with a few photos of Stewart, asking the bartender permission first. “Yeah, go ahead,” he waved in response. Though another guy chimed in with mock seriousness, “Hey!” he yipped. “We’re expecting royalties from this.”
The Making of the Mob premieres Monday, June 15th at 10 pm EST on AMC.