A Gangster's Gangster: Bugsy Siegel's Life and Times

Born in 1906 to poor Jewish immigrants, Benjamin Siegel's early life followed a kind of blueprint for young thugs: A restlessness and distaste for rules led him to drop out of school early, street gangs provided him with a sense of identity, and the allure of easy money pulled him into breaking the law.

As a youngster, he and his gang members forced neighborhood business owners into paying them in a "protection racket." During Prohibition, they ran liquor to speakeasies. They fought with rival gangs, including the Italian Mafia. They gambled. Stole. As a teen, Siegel partnered with another young Jewish outlaw, Meyer Lansky, to form a gang that served as the enforcement arm for several East Coast bootlegging operations and crime syndicates. They did more than break a few legs to enforce the mob rules; they, and others, killed.

By the time he was in his early 20s, Siegel had made enough money to buy an apartment at the Waldorf-Astoria Hotel in New York City and a house in the northern suburbs. He was husband and father to two girls and a regular on the New York City nightlife scene. At that point, already, there was no going back.

"Those who have studied immigrants in the first two decades of the 20th century point out that everybody they came across struggled to do well," Gragg says. "But these guys — and when I say these guys, I mean Meyer Lansky, Ben Siegel, Lucky Luciano, [Louis] 'Lepke' Buchalter, and folks like that — they didn't want to work. They didn't want to have an 8-5 day. They wanted the easy way out, and the easy way out was crime."

Siegel was still in his early 20s when he was said to have been hired for the killing of a New York City mob boss, which led to a reorganization of organized crime in the city. Siegel and Lansky formed an association with others that the press dubbed "Murder, Incorporated," a national for-hire hit squad designed to keep order among the crime families. During the 12 years of its existence, the group reportedly killed hundreds. Siegel was never convicted.

As Siegel became better-known to law enforcement, he ventured westward, sent to oversee (and eventually take over) illegal gambling operations on the West Coast. He dove into the drug trade and into prostitution, invested in real estate, and dabbled in the entertainment business. At one point, according to Gragg's research, he was making $20,000 a month. That's about $373,000 a month today, or $4.4 million a year.

He socialized with the likes of Frank Sinatra, Cary Grant and Jean Harlow. He was always well-dressed, and described as handsome, smooth and charming. But, true to his criminal roots, he had a dark side.

"He had a hair-trigger temper," Gragg says. "He would either abuse you verbally or just punch you if you used that name he didn't want used: 'Bugsy.'

In conversation, even Gragg will say "Siegel" or "Ben" when discussing his subject.

"What I found from memoirs of many people and in news accounts, he would just completely fly into an outrage if somebody [called him Bugsy]." Gragg says. "He had this awful temper. And he used it well. They were afraid of him. They were afraid of crossing him."

Other than his violent death, Siegel may be best known for his connection to Vegas, which in the 1940s was just beginning to realize its potential as a gambling and entertainment capital.

A scene in "Bugsy" has Beatty, as Siegel, undergoing an epiphany in the desert, suddenly envisioning huge casinos, top-notch acts, and gamblers coming from all over the world to spend money, legally. That scene fueled the notion of Siegel as the visionary behind modern-day Vegas.

"It's a wonderful scene, but it's just flat-out wrong," Gragg says. "The idea was the brainchild of the owner and the editor of The Hollywood Reporter, Billy Wilkerson, who was a compulsive gambler. He wanted to build a luxury hotel/casino in Las Vegas, and he started it, but he ran out of money, and the mob took over, and Siegel saw an opportunity to embellish somebody else's idea."

The hotel/casino was the Flamingo, the first modern resort and perhaps the most influential on what is now known as the Las Vegas Strip. With Wilkerson out of funds, Lansky and the mob sent Siegel to take over. Knowing little about construction or how to run a casino, he quickly ran into trouble.

The casino and dining room, with the hotel still incomplete, officially opened Dec. 26, 1946, with Jimmy Durante headlining the entertainment. It lost $300,000 in its first week. It closed a couple of weeks later, reopened once the hotel was ready (in March 1947) and soon — thanks in large part to Siegel's Hollywood connections and his insistence on quality entertainment (Lena Horne, the Andrews Sisters, Abbott and Costello) — became a success.

"He really did kick off the idea that you pay top dollar for the best entertainers, and you don't charge all that much for a hotel room, even though it's a luxurious hotel room," Gragg says, "so he does get some credit. Considerable credit. But he can't be perceived as the visionary of Las Vegas."

No one has proven who murdered Siegel almost 73 years ago. We have murder scene and autopsy photos. We know some gruesome details. A single shot, for example, forced one of Siegel's eyes out of his head; it ended up several feet away on the dining room floor. (In "The Godfather," Moe Greene is killed by an assassin, who shoots him in the eye, through his eyeglasses, as he's getting a massage.)

No one knows, or has proven, a motive, either. The most common theory is that Lansky had his boyhood friend killed for stealing from the mob and, perhaps, bungling the opening of The Flamingo. Another suggests the shooter was someone that Siegel had beaten and embarrassed. Yet another, detailed in a 2014 Los Angeles Magazine story, "Who Killed Bugsy Siegel?" says that he was gunned down by "Moose" Pandza, the lover of the wife of one of Siegel's boyhood friends and his everyday partner in The Flamingo, Moe Sedway. (The theory there is that the wife had her lover kill Siegel because he was about to murder Moe.)

The case remains, officially, an unsolved murder.

"It's most likely that he had so angered the leaders of organized crime who had invested in The Flamingo that they had ordered a hit on him," Gragg says. "But the trouble with that guess is that most people say they made that decision either in December of '46 or early '47, but he's not murdered until June. If you believe a guy should be gotten rid of, why would you wait six months?

"I legitimately don't have a good guess."

And so the mystery surrounding the death of one of the most well-known gangsters in American history remains. And the mystique of the man some dared to call Bugsy grows.

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