Benjamin Siegel, born in Brooklyn in 1906, hated his nickname, that derived from his volatile temper. He was on the path to organized crime from a very young age, demanding protection money from pushcart vendors.

Halfway through his teen years he met Meyer Lansky, with whom he formed the Bug & Meyer Mob, a gang that dealt in gambling and car theft. The Bug & Meyer Mob teamed up with Lucky Luciano and his gang in 1930. Luciano allegedly used Siegel to kill Joe "The Boss" Masseria, a move that ended that Castellammarese War. Siegel continued to carry out murders for Luciano and by 1937 there were a number of contracts out on him because he had angered several bosses.

Luciano and his crew decided that it would be best for Siegel to leave for the West Coast to escape the wrath of several of his enemies, and to set up new syndicate rackets in California. There he met a large number of Hollywood stars, as well as studio owners such as Jack Warner and Louis B. Mayer, both who he would contact later to extort money from. He also met Virginia Hill, a money runner for the Chicago Mob, and who had a penchant for blackmailing Hollywood stars.

In the mid-40s Siegel used about $5 million of syndicate money to construct the first super-casino/hotel, the Flamingo, in Las Vegas. When the opening of the casino turned out to be a fiasco, and the money did not start flowing in as expected, Luciano demanded that Siegel return the $5 million he had used. Siegel, figuring himself as big and powerful as Luciano, told him to "go to hell." In reaction, Luciano ordered to have Siegel killed. On June 20, 1947, as Siegel ast in Hill's living room, he was shot three times in the head. Neither Hill nor any of his Hollywood friends attended his funeral.