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Tough Teddy and Old Hickory: America’s Most Badass Presidents

Khalid Elhassan December 4, 2024 14 min

Tough - An 1828 woodcut of the Andrew Jackson vs Charles Dickinson duel — An 1828 woodcut of the Andrew Jackson vs Charles Dickinson duel. Wikimedia

8. When Teddy Roosevelt Walked Into a Seedy Bar

Tough - A bespectacled Teddy Roosevelt out West, on horseback — A bespectacled Teddy Roosevelt out West, on horseback. Theodore Roosevelt Presidential Library

The Nolan Hotel looked like a seedy dive, and Teddy Roosevelt was reluctant to enter – especially after he heard a pair of gunshots coming from the bar. However, nightfall was near, and it and it was cold outside. So he went in. He saw a “shabby individual in a broad hat with a cocked gun in each hand was walking up and down the floor talking with strident profanity. He had evidently been shooting at the clock, which had two or three holes in its face“. Soon as he saw TR, who wore glasses, the lout hailed him as “Four Eyes”, and announced to the bar that “Four Eyes is going to treat!” The future president tried to play it off as a joke, but the loudmouth followed him around.

Written by

Khalid Elhassan

A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.