Al Capone: Chicago's Most Infamous Mob Boss

Chicago was a perfect place to build a criminal empire.  It was a rowdy, pugnacious, hard-drinking town that was open to anyone with enough money to buy it.   In the words of one of her top journalists, "She was vibrant and violent, stimulating and ruthless, intolerant of smugness, impatient with those either physically or intellectually timid."  It was a bloody and brutal city where tens of millions of cows, hogs and sheep were slaughtered by men wading through blood on the killing floor.  It was strictly a commercial town with no appetite for snobbery or "old money."

Political corruption was a tradition in that vast prairie city, creating an atmosphere of two-fisted lawlessness in which crime flourished.  The city became known for its wealth and sexual promiscuity.  When Al Capone came to the city in 1920, the flesh trade was becoming the province of organized crime.  The kingpin of this business was "Big Jim" Colosimo along with his wife and partner, Victoria Moresco, a highly successful madam.  Together their brothels were earning an estimated $50,000 per month.

Big Jim owned the Colosimo Cafe, one of the most popular nightclubs in the city.   Nobody cared that he was a pimp.  It never stopped him from hobnobbing with the rich and famous.  Enrico Caruso was a regular, as well as the distinguished lawyer Clarence Darrow.  Big Jim, with huge diamonds glittering on every one of his fat fingers and diamond-studded belts and buckles, was a true product a Chicago society --handsome, generous, gaudy, larger than life.

As his family vice business grew, Big Jim brought in the discreet Johnny Torrio from Brooklyn to operate and grow their empire.  It was the best decision he could have made because Torrio expanded their business without attracting attention.  Torrio was a serious businessman with no interest in hanky-panky.  In stark contrast to Big Jim, Torrio didn't drink, smoke, swear or cheat on his devoted wife Ann.

The downfall of Big Jim was Dale Winter, a pretty young singer who stole his heart.  He foolishly divorced Victoria and married the young singer immediately afterward.  Word of Colosimo's folly got back to Brooklyn where Frankie Yale took notice of opportunity and decided to muscle in on Colosimo's huge empire.  On May 11, 1920, Yale assassinated Big Jim in his nightclub.

Bergreen describes the first of Chicago's great gangster funerals:  "the last rites became a gaudy demonstration more appropriate to...a powerful political figure or popular entertainer...an event that priests and police captains alike attended to pay their last respects to the sort of man they were supposed to condemn.  Colosimo was universally recognized as Chicago's premier pimp, yet his honorary pallbearers included three judges, a congressman, an assistant state attorney, and no less than nine Chicago aldermen."

Eventually the police figured out who the murderer was and they arrested him in New York.  However, the only witness to the murder was a waiter, who refused to testify against Frankie Yale.  While Yale was able to avoid prosecution, his attempt to take over Colosimo's empire failed.  Torrio was able to maintain his grip on the vast multimillion-dollar-a-year business he had built for Big Jim.  With a big boost to business from Prohibition, Torrio oversaw thousands of whorehouses, gambling joints and speakeasies.