• Dennis McCaslin

Chronicle of the Old West: You only stole from Teddy once...if you knew what was good for you



On March 24, 1886, three hard cases were on the move. Unfortunately, an ice-swollen river stood between them and their destination. They came across a small rowboat, and decided to commandeer it.

Now, normally the owner would chalk it off as a loss, but not this owner. He happened to be a tenderfoot easterner who had recently become the chairman of the Little Missouri Stockmen’s Association, a position that also carried with it the title of deputy sheriff.


This easterner turned cowboy and rancher was a man of grit and determination who was later to hold the highest office in our land.


His name was Theodore Roosevelt. 

Roosevelt had another boat made, and within a week, he and two cowboys were going after the thieves. After three days, they found them.

Because of the icy river, the group traveled eight days trying to get back home. With provisions almost gone, they finally came across a ranch.


Roosevelt hired a wagon and driver to take him and the three ruffians the rest of the way. Roosevelt’s two companions remained with the boats.

It took two days and a night to get to the nearest town. Roosevelt stayed awake, with rifle at the ready, the whole time. To make sure he wasn’t jumped, Roosevelt had to walk along behind the wagon.

As deputy sheriff, Roosevelt received a fee for bringing in the men, and mileage for the over 300 miles he had traveled to retrieve them.


It was a total of $50. But he had accomplished two things: First, he had upheld the law.


Second, people would think twice before stealing anything from him again.



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