The Chicago Police and Five Unsolved Mysteries

It may be hard to imagine, but the Chicago police department is probably better respected today than they ever were before. Of course, this isn’t saying much. In the 1800s, they had a reputation for spending most of their time “interviewing” bartenders, and a consultant hired to look into their activities in 1904 said that “I would wager $25 that in one precinct I can find twenty-seven policemen violating the law inside of three hours. The police of Chicago are piano movers, bums, cripples, janitors, ward heelers – anything but policemen.” Here are a few times when the historical Chicago police left us with lingering mysteries.


  1. Alice Montgomery

In 1881, young Alice Montgomery collapsed in a Madison Street boarding house. An autopsy showed that she’d recently undergone an abortion, and the painkillers contained entirely too much strychnine. Only steps away from the boarding house was the office of Dr. Thomas Neill Cream, who would be arrested for another murder months later, spend time in Joliet, then be hanged in London for murdering abortion patients with strychnine. His case attracted national attention, and it’s remarkable that no one on the force remembered Alice Montgomery. How many strychnine-happy abortionists could there have been operating around Madison and Throop?


  1. The Holmes Trunk

In 1897, John J. Badenoch, a completely unqualified police chief, was sued by Patrick Quinlan, who had been the janitor at the famous H.H. Holmes “murder castle.” Badenoch’s eagerness to think he’d solved every crime of the past decade is largely responsible for the wild stories about the building, which has been made famous all over again by Erik Larson’s smash hit Devil in the White City. Quinlan had been held in custody and interrogated for three weeks without any real evidence against him. That was bad enough, but the real mistake is that, as of the trial, they still had a trunk of bones, photos, and other evidence related to Holmes. Since then, the trunk, which would be incredibly useful to Holmes researchers, has disappeared. The bones in the trunk could go a very long way toward proving that Holmes was guilty of murder in Chicago—something the police were never able to do.


  1. The Kangaroo of Jefferson Park

In 1974, the Chicago papers broke the story that a kangaroo had been spotted around Jefferson Park; the Tribune even said that a police officer had tried to handcuff the fugitive marsupial and was “thoroughly kicked” in return. The story became a national joke, reaching what we’d now call “peak kangaroo” when President Ford came to town and made a wisecrack about the Democrats registering the kangaroo to vote. Though sighted for days, the kangaroo was never caught, no missing kangaroo was reported, and most came to think of the whole story as a newspaper hoax. But the police officer in question insisted that it was real, and that they had a good idea where it came from, but that the chief, embarrassed by the ordeal, ordered him to tell the press it was all a joke.

The Chicago Police and Five Unsolved Mysteries

  1. The Lonesome Death of Barton Edsall

In the early hours of October 6, 1871, wealthy Chicago merchant Barton Edsall was found dead in the entryway of his north side mansion. For two days, all Chicago argued about whether he’d been shot by a burglar, had killed himself, or if the shooting had been accidental. The inquest ran for two days, and it’s difficult now not to read the transcripts and scream at the police for their poor grasp of basic forensics. But it wasn’t really their fault this time; such forensics were beyond the reach of most investigators in those days, and on October 8, the day Barton was buried, the crime scene and all of the evidence were destroyed—along with the rest of the city—in the great Chicago fire.


  1. The Lipstick Killer

In 1946, Chicagoans were terrified by a series of brutal murders; one such murder featured a crime scene at which the killer (or perhaps an enterprising reporter) had scrawled the words “For heavens sake, catch me before I kill more” on the wall in lipstick. Whether Richard Heirens, the young man they eventually arrested, was truly the guilty party is still a matter of debate, but the police force’s treatment of their suspect was appalling. Lying in a hospital bed after being badly injured in the chase, he was given a spinal tap without anesthesia, had ether poured on his genitals, and was injected with sodium pentathol without consent. Much of the evidence against him was found to be manufactured or tampered with, and the police interrogations were a textbook example of how to extract a false confession. Despite strong doubts as to his guilt, Heirens remained in prison until his death in 2012.

Adam Selzer is an author and tour guide in Chicago. Recent books include Just Kill Me (Simon and Schuster), a novel about a ghost tour guide who makes places more haunted by killing people at them, and the new Mysterious Chicago book from Skyhorse. See his blog and podcast at