Community Corner
'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.
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.
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