Jim Colosimo, the Infamous Crime Boss Who Tied the Knot at West Baden


Jim Colosimo and Dale Winter on the fountain outside West Baden Springs Hotel, during their honeymoon here in 1920. 


If you followed our blog series over the last three weeks about Al Capone, maybe you’ve developed your own take about whether one of America’s most infamous gangsters visited French Lick and West Baden back in the day. (And in case you missed it, catch yourself up on the first, second and third installments on Capone.)

Nobody can prove for certain whether or not Capone was here. But another infamous, albeit lesser-known gangster, was here. And we can prove that.

Here’s a little snapshot of Jim Colosimo. A.k.a. “Big Jim.” A.k.a “Diamond Jim,” as he was decked out with diamonds on his tie, jacket, suspenders and belt just as you’d expect from any good crime boss. Jim grew up shining shoes and selling newspapers on the streets of Chicago to help his immigrant family eat. He worked as a street sweeper and began organizing them to unionize. And so it progressed, into ward politics and rackets including brothels.

In 1910 Jim opened a café under the Colosimo’s name, famous for its fine Italian food, wine and characters who gathered every night in Chicago’s red light district. A woman named Dale Winter worked at the restaurant as a singer, and she caught Jim’s eye. Big Jim, the infamous vice lord, was smitten with the angel-voiced girl who was 17 years younger and sang in the church choir. They seemed like polar opposites. But you know how those types tend to attract.

In March of 1920, Jim secured a divorce from his wife. The following month, he and Dale eloped and ran off nearly 300 miles to a tiny town called West Baden Springs, Indiana. Prior to this two-week honeymoon, Jim had actually occasionally vacationed at West Baden Springs Hotel since about 1910. He became close with Ed Ballard, the mogul who owned underground casinos and real estate interests in the area (and later took ownership of West Baden Springs Hotel). He also developed a friendship with a man named Lafe Prow, the night auditor of the hotel who saw to all of Big Jim’s needs during his visits.

Jim and Dale got married at West Baden Springs Hotel on April 17, 1920, in a small ceremony on the front steps leading up to the hotel. A photograph was taken of the two of them seated on a fountain ledge with the hotel in the background. They’re wearing riding attire, apparently either just finishing a horseback ride or about to begin one. (The photo is at the top of the page.)

Jim and Dale's reception was in the ballroom at West Baden Springs Hotel, and they invited any guest staying at the hotel to attend. The old ballroom was located on the third floor, above the dining room. 

Their actual ceremony was private one with just a few people attending. But the reception was open to anyone and everyone. Jim may have been a ruthless crime boss, but he was also a benevolent soul — so much so, that he invited any guest staying in the hotel that day to attend the reception. The party took place in the hotel’s ballroom, located on the third floor directly above the two-story dining room, and wild animals from the circus that Ballard owned were even brought to the reception to add to the spectacle. (Just imagine the story you’d be able to tell if you were staying at the hotel that day and got a spontaneous invite to a mobster’s wedding.)

When Jim and Dale returned to Chicago, their marriage wasn't lengthy. Less than one month after their wedding here at West Baden, Jim was shot and killed in the vestibule of his café in Chicago. The murder went unsolved, but a popular theory is that Al Capone was the one responsible for pulling the trigger or ordering the hit. Shortly after Jim’s murder was when Capone began his rise in Chicago’s world of organized crime.
Big Jim and Dale Winter are two of the costumed
characters who tell their stories during West
Baden's Twilight Tours, which pick up again in
May-September of next year.

To this day, the Capone name rings far more bells than Colosimo does — even though Big Jim was larger than life during that era. He was in power longer than Capone in Chicago’s crime empire. Thousands turned out to the Chicago streets for his funeral, and he had 53 pallbearers at his service — Ed Ballard being one of them.

Today at West Baden Springs Hotel, you can “meet” Big Jim and Dale Winter at the special Twilight Tours that pick up again May-September of next year. They’ll tell you all about their West Baden wedding as the two are costumed characters who share some of West Baden’s history from a first-person perspective.

And any time you visit, walk outside and imagine one of the most infamous crime bosses of the era getting married right on the front steps of West Baden. It may seem too crazy to believe — but there’s proof of this gangster’s visit.