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'Dreadhead Cowboy' Spotted Riding, Flipping Off Horse In Downtown Chicago

CBS Skywatch spotted him, and at one point, officers stopped a woman riding the horse.

(CBS Chicago)

September 23, 2025

The man known as the so-called "Dreadhead Cowboy" took to the streets in downtown Chicago on Monday afternoon, while riding and performing flips off a horse.

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CBS Skywatch spotted him, and at one point, officers stopped a woman riding the horse.

In 2020, this same man, Adam Hollingsworth, was charged with aggravated animal cruelty after he rode a horse for several miles on the Dan Ryan Expressway.

Find out what's happening in Chicagofor free with the latest updates from Patch.