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 of a horse. 

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.

In 2023, he was also spotted riding a horse in Hammond, Indiana. He was also arrested and charged with elbowing a police officer there.

CBS News Chicago asked police if people can ride a horse in downtown Chicago for travel. They could not provide an answer.

People, however, cannot ride a horse or a horse-drawn carriage downtown for commercial purposes.