"The higher the type of man, the greater the improbability that he will succeed."
                                                                                                   —NIETZSCHE

Luigi Colosimo's boy Jim shined shoes on the Chicago streets to help his immigrant family eat. He sold papers. He ran errands for the small-time hoodlums of the South Side slums. He stole. He carried water for a railroad section gang. He worked as a street cleaner. He got into ward politics and the rackets. He became the maestro of a brothel. He married Victoria Moresco, his childhood sweetheart, and made her a madam—in an Armour Avenue house, that is. As he prospered, he branched out into bootlegging (a pretty good trade even before Prohibition) and the saloon business.

By 1920, Big Jim Colosimo was a walking ad for the new American nobility. He was wearing diamonds—on his tiepin, his studs, his suspenders and belts, his watch fob, and even on his garters. And he had a respectability befitting his station in life. His restaurant at Wabash Avenue and Twenty-Second Street in the Red Light district became a Chicago showplace. There in the late hours you might see the Great Caruso, or Luisa Tetrazzini, or Amelita Galli-Curci, or Flo Ziegfeld, or George M. Cohan, or Gentleman Jim Corbett, or John McCormack. Everybody knew about the splendid vino and Italian dishes at Colosimo's and everybody knew the genial proprietor, especially the opera people. Big Jim, who carried a cane and wore a Homburg, loved the opera with passionate devotion. He loved a fine voice. That could have been what killed the first of the Windy City's overlords of crime in the Lawless Decade.

A songbird named Dale Winter came into town one icy winter in search of a living. An Ohio girl, she had sung light opera in New York, San Francisco, and Australia. Now she was out of work. Somebody brought her to Colosimo's cafe. Big Jim liked the voice—and the flesh, too. He put Miss Winter on the night shift in his cafe, enrolled her in the Chicago Musical College with Caruso's help, and had her do part-time choir duty in the South Park Avenue Methodist Church to keep her vocal cords polished at all times. The church connection didn't last long. A straying elder saw Miss Winter in the gilded Colosimo dive and tattled. The pastor defended the girl but the songbird fled anyway.

In March, 1920, Big Jim shed his wife Victoria, the light of his life in poverty and in riches, in favor of Dale Winter. "This is the real thing," Colosimo told Johnny Torrio, who replied, "It's your funeral, Jim." The forty-nine-year-old gangster settled $50,000 on Mrs. Colosimo and married his beautiful young thrush. The oddly-matched pair spent a quick honeymoon at French Lick (Indiana) and repaired to the Colosimo mansion on Vernon Avenue. They had barely settled down for the long matrimonial pull when, on May 11, Big Jim excused himself to meet someone on "urgent business" before his restaurant opened. The business proved to be murder—and the victim was Colosimo.

There were numerous theories behind the slaying. The first had to do with the deceased's amours. It was said that his casual discarding of Victoria Moresco had suggested to the underworld that no vestige of loyalty or dependability remained in the man, so everybody would be better off without him. It was also said that he had fallen out with Torrio, his very own lieutenant, and that Torrio himself had summoned him to his rendezvous with death. And it was said that the long arm of vengeance simply had caught up with the diamond-studded flesh peddler. Police had linked Big Jim to twelve murders in the years of his rise, including the violent departure of three Black Hand agents who once demanded that he present himself under a South Side bridge with a goodwill offering of $5,000. The shakedown crew expired under the bridge in the fire from two Tommy guns, one supposedly held by Colosimo himself.

Big Jim had the first of the gangland funeral extravaganzas of the twenties—a $50,000 affair that drew a good representation from the ranks of Chicago officialdom and its cultural life, along with the underworld nobility and its hangers-on. There were judges, policemen, aldermen, pimps, opera stars and actors, but little John Torrio shed the most noticeable tears. "We was like brothers," Torrio said as the ex-white-wing was lowered into the grave.

The estate was supposed to come to $2,000,000 but only $40,000 turned up for the records. The widow Dale spurned her share and instead relied on the golden tones that her late husband's goombah, Caruso, liked so much. She did a long run in Irene on Broadway and then married well and disappeared from the public prints.

The principal benefactor of Colosimo's greater wealth which lay hidden in its vast potential was the brainy Torrio. He picked up the scepter following his brief show of public mourning for the man who had brought him to Chicago to put him on the golden ladder. It was the event of the Prohibition-time boom in the rackets. Torrio had an empire to build. And, like Colosimo before him, he sent to New York for a good right bower to keep him, healthy, or at least bulletproof. He sent for Al Capone.