Mildred Bolton: The first woman to escape Chicago’s electric chair

If you enjoy reading about classic crime stories, it’s certainly not too difficult to find some truly interesting characters. For instance, take convicted killer Mildred Bolton. If you don’t recognize the name, I can tell you she almost became the first Illinois woman ever executed in Chicago’s electric chair.

Before we get to Mildred’s story, I have a question for you. Have you ever seen a couple that just didn’t seem right for each other? It could be a close friend or even a relative. We have all seen this couple. Everything is wrong about them. They share no common interests, or one is a loudmouth braggart while the other is meek and rarely speaks out of turn.

There was a Chicago couple back in the early 1920s who fit this description. Joseph Bolton Jr., was a successful businessman who worked in the insurance business. He was reserved and wore glasses. In 1922, he married Mildred, a troubled woman who would be his undoing and ultimately be the death of him.

Although Mildred had her issues during the beginning of the marriage, they would only get worse with time. For unknown reasons, Mildred had it in her mind that Joseph was the object of desire for many women. Mildred thought he drew women in like some kind of sex magnet. And this just wasn’t true.

Joseph never kept company with other women. He was so shy that he could barely get the words out when speaking to a woman. Mildred eventually became unhinged and began stalking her husband at work. She would constantly show up at his office and accuse female coworkers of carrying on with Joseph. None of her accusations were true.

The marriage that never should have happened

It got so bad for Joseph that his employer forced him to leave the company. The couple then moved to Chicago in 1928 so Joseph could start his own insurance business. But life never got any better for mild mannered Joseph. He feared Mildred. He knew she had a few missing screws. He also became convinced she wanted to kill him.

Mildred eventually began physically assaulting her husband. She would knock his glasses from his face and strike him in public. She claimed no Cook County jury would ever convict a woman for killing her husband. And behind closed doors, Mildred often tried to stab Joseph with razors and knives. The police were regular visitors to the Bolton home because of domestic disputes between the couple.

On July 22, 1934, a police officer was dispatched to a Hyde Park drug store. Someone had stabbed a victim in the forearm. The victim was bleeding heavily. During Joseph’s transfer to the hospital, the officer visited Mildred and asked what had happened because Joseph didn’t identify his attacker.

Mildred told the officer Joseph cut himself shaving. The officer didn’t believe this because the cuts said otherwise. Regardless, Joseph refused to name Mildred as his attacker. Two years later, Joseph moved on from his abusive wife. He filed for divorce. Mildred wasn’t having it. She bought a pistol and six bullets. And I am sure each one had Joseph’s name on it.

Days after buying the pistol, Mildred visited Joseph at work. She rode the elevator ten floors to meet with her husband. She entered his office and shot Joseph. As he writhed on the ground in agony, she told him to stop faking his pain. Joseph Bolton Jr., didn’t survive the shooting and died shortly after. The police immediately arrested Mildred. She claimed Joseph had committed suicide. But the two bullets in Joseph’s back didn’t point to a suicide.

It would only take a jury a little over thirty minutes to convict Mildred of murder. She was sentenced to be executed in the electric chair. She should have become the first Illinois woman to be executed in Chicago’s electric chair. But this never happened. A judge commuted Mildred’s death sentence. Mildred received 199 years in prison.

She had a brief sentence. On August 29, 1943, she committed suicide by using a pair of stolen scissors to slash her wrists. Her last words? They appeared in a note, “I wish to die as I have lived, completely alone.”

Wish granted Mildred.