The Dock Walloper

This is part one of a two-part story; part two is Shawshank Anticipation.

Dear Friends: At the end of a very strange semester, I write with the wind shrieking and the branches at my window scratching loudly against the frame – which means it is the season for Scary Story Time. I hope this is a welcome diversion from your work and studies – but prepare yourself. The story, as always, is true.

In May 1887 Henry McCabe was a sullen-faced tough. He was in his early 30s, frequently drunk, often arrested. At one time he had been a sailor, but now he worked as a dock walloper, an old term for a type of longshoreman: McCabe moved heavy things on ships and railcars. When he was in his cups, he could be a very dangerous man.

Chicago saloons
South Side of Chicago, late 19th century

Not long after he began drinking, McCabe noticed a well-dressed man spending money – and drinking – liberally. McCabe saw an opportunity and made a new friend.

After a few drinks the two men took a short walk to Breen’s for a couple more. Leaving Breen’s they headed to Jim Brennan’s Saloon, just across the Halsted Street bridge. Along the way McCabe spoke with the bridge tender, who noted that McCabe was wearing his usual black derby hat.

After Brennan’s, McCabe decided he’d had enough of saloons: he was ready to do some serious drinking. The men bought a bottle of whiskey, hopped on an empty wagon in Doyle’s Lumber Yard, and continued. 

Around midnight a watchman saw two men stumbling across the lumber yard. He spoke to one of them, who was well-dressed but so drunk that he was barely intelligible; the other fellow stayed in the shadows. The watchman did not sense any serious problems – apparently the scene was not unusual for Saturday night at the lumber yard – so he let the two men pass.

Not long after, the Halsted Street bridge tender saw McCabe for the second time that evening. McCabe was now alone, and he was missing his hat. The other man?

Photo of coupling pins
Photo from Central Pacific Railroad Photographic History Museum

The victim was Jim Howard, a Double Domer, decorated combat veteran of the Civil War, and once brilliant lawyer. He had suffered terribly in the two years since his wife had died, however, turning to the bottle for solace. He had gone to Chicago in an attempt to get his career back on track; at the encouragement of friends, he took an exam that would qualify him to serve on a government pension board. The hope was that a steady job would help calm his nerves. Howard performed well on the exam but, in a city teeming with temptations, he was unable to shake old habits. And so, shortly after the exam, he found himself with Henry McCabe on what would be the last night of his life.

McCabe was arrested within the week. He first denied any knowledge of the events, then changed his story to claim that after an argument Howard had fallen and struck his head. The jury didn’t believe McCabe’s story, but they also didn’t believe that he intended to kill Howard. They returned a compromise verdict: McCabe was responsible for the death, but the charge was manslaughter. He was sentenced to eight years in the state penitentiary at Joliet.

One year later McCabe was declared insane and was transferred to the asylum in Elgin. And that, dear reader, is where the story really begins.

Stay tuned for the next edition of Story Time. In the meantime, stay healthy – and keep away from lumber yards at midnight.


For sources and additional reading see p. 2

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