Dale Winters was born in 1891 in Ohio, and became a teenage beauty and singing talent. She arrived in Chicago in 1915 and auditioned as a singer at Colosimo's Cafe, by which time she was going by the singular, Dale Winter. Big Jim was impressed with her talent and he hired her on the spot at a rate of $40 per week.
Over time, Colosimo found himself increasingly attracted to this beautiful young woman, and her innocence awakened in him a desire to quit the rackets. A local clergyman, for whose congregation Dale sang, said, "she has the image of goodness written in her face." Colosimo paid for her to take singing lessons and attained for her a college scholarship to study music. During this time, Dale lived with her mother here, at 5716 South Parkway (now Martin Luther King Dr.).
Big Jim's wife, Victoria, was none too happy having her husband fawning over a teenager, and did everything in her power to separate the two. Finally, she could read the writing on the wall, and decamped for Los Angeles in 1920. Colosimo and Winter became more and more closely intertwined, and they were married on April 16, 1920 at the West Baden Springs Hotel in Indiana. After a short honeymoon, Dale moved into Colosimo's home on Vernon Ave.
Less than a month later, on May 11, Dale Winter was a widow. Colosimo was assassinated, probably at the behest of his lieutenant, Johnny Torrio. Dale Winter renounced all claim to Colosimo's money (no one else ever got much anyway), saying "All I want of Jim is the memory of him. I don't want his money or the things he gave me. I'm going to sing again. Maybe I'll sing better. I know now there isn't much to life except giving something to others. There'll never be anything in my life except singing and remembering and singing."
Dale Winter went on to a moderately successful career on Broadway, and occasionally, in film. She married again in 1924 and moved to California, where she and her husband operated a chain of theaters. Her husband died in the 1960s, and she remarried again twice, each time becoming a widow.
Dale Winter passed on in 1985 at Santa Barbara, California.