Chicago’s More Notorious Crimes

  1. Prison BarsThe “Devil in the White City” murders/ H.H. Holmes’ Murder Castle

Born Herman Webster Mudgett around 1860, he changed it to H.H. Holmes when he became a Doctor. At the time of the Chicago World’s Fair in 1893, Dr. Holmes built a three story hotel dubbed the World’s Fair Hotel. He used multiple construction companies and architects to prevent anyone from exactly pinning down what the Hotel was being designed for. Replete with rooms with no windows, false floors, secret passageways, trap doors and chutes, Dr. Holmes used his hotel to become one of America’s first, and possibly, most prolific serial killers ever.

Although only 9 people were actually confirmed murdered by his hand, his wild and varying statements included a confession to 27 killings (although some of his “victims” were found to be alive), and it is also believed he killed upwards of 200 people during the 5 months the World’s Fair ran in Chicago. Besides mass murder, he was also involved in insurance fraud schemes, and was even wanted for Horse Theft out of Texas. It was the warrant for his arrest on this horse theft that led to his undoing. Wishing to avoid the “swift and sure” justice in Texas, he confessed to an insurance fraud scheme involving his deceased former partner.

Apparently, he murdered his former partner, and tried to collect on a life insurance policy. When the body was found, it was in full rigor mortis, which lasts only a few days. But he claimed to the investigator taking his statement that he got the body from an outside source, and placed it in the trunk where it was found. Realizing that the body was recently deceased when found, the investigator determined that Dr. Holmes was lying. Confronted with that fact, he ultimately confessed to the murder. He was sentenced to death and hanged in 1896. His “Murder Castle” burned down to the ground in 1895.

At his request, he was entombed inside and under ten feet of concrete, in order to thwart would-be grave robbers from exhuming his remains and dissecting them. Considering the gruesome nature in which he tortured and killed his victims, this was a rather ironic request.

More on that story here.

  1. Leopold and Loeb, “The Perfect Crime”

These two young men were students at the University of Chicago, where they met and developed a romantic friendship. Avid readers of Nietzsche, and his philosophy of “Ubermensche”, or Supermen, they believed themselves to be “above” societal norms and laws, and set out to see if they could commit “The Perfect Crime.” Their chosen victim, a lad named Bobby Franks, was a second cousin to Loeb. It is believed that Loeb offered his cousin a ride home, and Leopold hit him repeatedly in the head with a chisel, then pulled him in the back seat and gagged him until he died. At the time of their arrests, Leopold and Loeb pointed the finger at each other as to who was driving, and who was doing the killing. They dumped the body in a remote location, and sent a fake ransom note to deflect suspicion of their involvement. However, the kidnapping ruse was quickly uncovered when Frank’s body was discovered a few days later. It is likely that the crime would have remained unsolved in those days before DNA testing began, but for a key piece of evidence found at the scene where Franks’ body was discovered: a set of eyeglasses that had a very unique latch that was so rare, only three men in the area owned them, one of whom was Leopold. If that were not enough, the ransom note was traced to a typewriter that Leopold had “borrowed” from his fraternity at University of Chicago. Although the State tried to get the Death Penalty in their cases, Clarence Darrow made an impassioned plea to the Judge which resulted in a 99 year jail sentences for both.

  1. The St. Valentine’s Day Massacre

On February 14, 1929, seven members of Chicago’s North Side Irish Gang, run by “Bugs” Moran, were brutally gunned down in a garage. The crime was committed by four men, two dressed in police uniforms, the other two in plain clothes. They lined the victims up against a wall, and blasted them with machine guns and shot guns. Afterward, the two uniformed men led the two plain dressed men at gun point, as if they were arresting them. The one victim found alive at the scene died within a few hours without ever revealing the names of the attackers. Although the Capone South Side Italian gang was widely believed to be responsible for the crime, no arrests were ever made, and when Capone finally did go down for a crime, it was for tax evasion only.

More on the story here.

  1. “The Lipstick Murderer”, William Heirens

Convicted in 1946 for the brutal, bloody murders of three women, William Heirens earned his moniker by writing, in lipstick on a wall:
For heavens
Sake catch me
Before I kill more
I cannot control myself

In addition, he also left a bloody fingerprint, and eyewitnesses that were able to describe him to the authorities. Mr. Heirens achieved even greater notoriety as Illinois’ longest-lived prisoner, for when he died in prison in 2012, he had served over 65 years of his sentence. There were those who doubted whether he was truly the killer, and he himself recanted his confession, saying that he was beaten and drugged in order to coerce his confession. He claimed he pleaded guilty to the three murders to receive a life sentence on each, rather than go to trial and face the death penalty. “I confessed to live” he was quoted as saying.

  1. Richard Speck Murders

On the evening of July 13, 1966, eight nurses sharing a dwelling were murdered, some from strangulation, some from stabbing. Mr. Speck entered the ladies’ home, took them all hostage at knife point, and herded them into a room. One by one, he led them out, then either stabbed or strangled them. His last victim he raped prior to killing her. Officers described the murder scene as a “bloodbath.” Mr. Speck was identified by a finger print left at the scene, as well as by a ninth nurse who somehow managed to hide under a bed, unseen by Mr. Speck, while he committed these unspeakable acts. After his arrest, in his statement to police, he claimed that he was drunk and stoned at the time, that he only intended to rob the nurses, and that he had no idea how that became a mass murder. While he was originally sentenced to death, that sentence was commuted to life in prison after an appeal. While in prison, he achieved further notoriety thanks to a contraband video camera that was used to film him in the act of using cocaine, and having sex with another inmate. Somehow, he also managed to grow very large breasts, possibly with the aid of female hormone drugs he had smuggled into the prison. He was heard in the video to be saying something along the lines of ‘if they knew how much fun I was having in here, they’d release me.’ He died in prison not long after that, having never been granted parole.

  1. Patricia Colombo murders

Starting in 1973, then 16 year old Patricia Colombo, who lived with her parents and brother in the northwest suburb Elk Grove Village, had a very strange sexual affair with her neighbor Frank DeLuca, a 39 year old, married, pharmacist. Her parents knew of the affair and did not approve. She would show her friends at school pictures of herself engaging in sexual acts with DeLuca’s dog. By 1976, both she and DeLuca were estranged from their families. They formulated a genius plan to murder her family, thus freeing up her inheritance. They shot her parents in cold blood, then bludgeoned her brother with a bowling trophy and stabbed him over 100 times with scissors. How were they ‘found out?’ The great Mastermind DeLuca actually approached several acquaintances of his to do the murders for them. Of course, they ‘ratted him out’ to the authorities after the murders. In an ironic twist, as it happened, there was no inheritance to be had for young Patricia, as her parents had written her entirely out of their wills. During her time in prison, Patricia organized sex orgies with guards and other inmates at the prison, and numerous prison officials had to resign or were fired in the wake of the scandal.

More on that story here.

  1. Detective Jon Burge

For decades, officers under the command of Jon Burge, a Chicago Police Detective, used torture of criminal suspects as a means of obtaining “confessions” which would then be used to obtain wrongful convictions of the suspects. Some of these forms of torture involved beatings with rubber hoses, being burned against a hot radiator, having a plastic sheet or bag placed over the head, and even administering electric shocks with wires attached to a hand-crank operated phone. For years, suspects would cry out in vain at their treatment, the courts all but ignoring their pleas at the time. It took years, and the development of DNA science to help exonerate the wrongly convicted. Even now, old cases are being rediscovered, and wrongful convictions continue to be vacated. The City of Chicago has paid millions and millions of dollars to settle civil claims arising from this utter fiasco. As for Mr. Burge, he was never charged criminally with a single violent act, as the Statutes of Limitations had long since expired. However, in the same way that Al Capone got away with murder only to be convicted of tax fraud, Burge was convicted of lying under oath in a civil action where he denied any knowledge of wrongdoing, and was sentenced to four and a half years in a federal prison. He was released to a half-way house in June of 2015 to serve out the remainder of his sentence, which has been fully served at this point.

More on that story here.

Written by Mitchell S. Sexner Last Updated : September 19, 2022