Big Jim Colosimo essentially founded the Chicago mob. In 1913 the news reporter Jack Lait came into Jim Colosimo’s café and ranted and raved about a young actress appearing at the South Park Avenue Methodist Church and he suggested Colosimo hire the young woman and put her in his floor show. Colosimo agreed to go and see the show himself and when he did he fell in love with 19-year-old Dale Winter of Ohio, who dreamed of a career as an opera star. She was chaperoned with her mother with whom she traveled. Colosimo left his wife and married Dale, telling Johnny Torrio, “This is the real thing.”

“It’s your funeral,” replied Johnny.

Dale did her best to add some polish to Colosimo, and slowly Colosimo started to change. He toned down his clothes colors for more conservative tones. She pulled him away from his Levee friends and politico types and soon the word went out, “Colosimo is getting soft.” which was essentially true.

When the divorce came through on March 20, 1920, his wife Victoria said, “I raised my husband from a boy to a man for another woman.” She took a $50,000 settlement. Twenty-four hours later Colosimo married Dale, the couple honeymooning in fashionable French Lick. Afterwards they returned to their mansion at 3156 Vernon Avenue and took Dale’s mother in with them. According to reporter Ray Brennan, Torrio, whom he recalled as a “little torpedo for hire, Johnny Torrio whose pop eyes and pursed mouth gave him a perpetually surprised expression,” ... had meetings with Chicago’s other leading gangster, Dion O’Bannion, the Genna’s and the Aiello’s, and discussed Colosimo’s pending assassination. They apparently agreed that it needed to be done.

A week after Colosimo’s return from his honeymoon, Torrio phoned him to say that two truckloads of whiskey were due into Colosimo’s café and Torrio would need to have Colosimo there for paper work and other odds and ends. Torrio was very specific about the time; Colosimo had to be there at 4:00 p.m. sharp. Annoyed at having to be troubled with the details of whiskey shipments, Colosimo agreed to be there and on Tuesday, May 11 he left his home at 3:45, decked out in his usual diamonds and pearls, a. 28 short nosed pistol stuffed in his right hip pocket. He kissed his wife good-bye and promised to have the chauffeured car sent back so she and her mother could go shopping. The driver noted that all the way to the café Jim sat crouched down in the back muttering to himself in Italian. The driver left Colosimo in front of the café at almost 4:00. Colosimo walked through the dark and empty café and went directly to his massive office in the rear and met with his secretary, Frank Camilla and the chef Caesarino and discussed the day’s menu. They said later that Colosimo looked troubled. He asked them if anybody had called him and when they said nobody had called he looked concerned and tried to reach his lawyer Rocco De Stefano by phone but couldn’t reach him. It was about 4:25. Colosimo walked out to the half darkened lobby where his killer or killers were hiding in the glass paneled telephone booth. The murderer fired two shots through the glass when Colosimo passed him, the first shot hit Colosimo in the head behind the right ear, and the second missed and hit the wall. Colosimo hit the tile floor face first. The killers rushed out from they’re hiding place, ripped open Colosimo’s shirtfront, withdrew his long leather wallet and fled. Inside the restaurant, there was a place set for one person, who had apparently been eating Italian ice cream with a glass of apricot brandy. The killer left a message on the check: “So long vampire, so long lefty.”

After Colosimo was murdered in 1920, Colosimo’s lawyers could only find $67,500 in cash and bonds and another $8,894 in jewelry in Colosimo’s estate. They had expected to find at least $500,000 in cash. Where the rest of Colosimo’s fortune went, nobody knows, and nobody ever found out.

Dale Winter’s Colosimo lay grief-stricken in her bed for ten days when word came that she had not been married to Colosimo due to a fine point in Illinois law which required that a couple take one year interval between divorce and remarriage. As a result of this oversight, Dale had no legal claim to what was left of Colosimo’s estate, however Colosimo’s family did grant her $60,000 in bonds and diamonds and gave another $12,000 to Victoria not to contest the split. The rest went to Colosimo’s father Luigi.

For a while Dale made a try at running Colosimo’s café but she just didn’t have the same touch for the business that Colosimo had so she sold her share to Mike the Greek Potzin who already had an interest in the place anyway. Dale and her mother returned to New York and became a Broadway success. She remarried to an actor in 1924 and was active in the theater throughout the thirties when she retired to San Francisco in the late 1940s