Charles “Chuckie” Crimaldi – Portrait of a Hitman

Chicago mob hitman Charles Crimaldi once explained his job this way: ”I’ve broken arms, and I’ve broken legs, and I’ve watched a man die with a knife in his throat. But most of them had it coming, so what’s the difference? I have no regrets.” This series of shows is taken from a 1973 Chicago Tribune series by reporter Robert Wiedrich. He titled this “Portrait of a Hitman.” This well-known mob reporter obtained a series of interviews with Crimaldi in a series of secret locations. We learn how Crimaldi had turned on his Outfit boss “Mad Sam” DeStefano because he had ordered him murdered. The reason for this was because Mad Sam had gone to prison and his wife, Anita, was going to close out the books on his loan sharking business. Crimaldi had expected to take over this business and was disappointed. Crimaldi claimed that Mad Sam did not want his books closed and his wife told her husband that Crimaldi quit the business and this caused his debtors to stop paying. Shortly after that, a man tried to run Chuckie Crimaldi off the road and Crimaldi viciously beat him and told him to take a message back to Mad Sam that he better send someone better than this to do this job. An enraged Mad Sam sent two others to murder Crimaldi and he was able to avoid them.

Sam DeStefano and the Leo Foreman Murder

The main thing that Crimaldi had on DeStefano was the murder of a gambler named Leo Foreman. He testified that Mad Sam DeStefano personally participated with Tony Spilotro in this murder. Crimaldi will help the government with several other Chicago outfit investigations before he is relocated to Texas.

The Death of Charles Crimaldi

After 40 years in hiding, Crimaldi died in 2020. He was living in Austin Texas and was using the name of Chuck Cazzola. He owned a plumbing company and brought a little of Chicago with him by starting a Chicago-style Italian beef stand in the Texas capital. In 1976, he co-wrote the book, Crimaldi, Contract Killer with journalist John Kidner. This book has gone on the rare book list with copies going for $150.00 and more.

Show notes by Gary Jenkins

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