Adam Hollingsworth, a Chicago man known as the “Dreadhead Cowboy” for previously riding a horse on the Dan Ryan Expressway in a protest, has been charged with operating an illegal bar and strip club called The Cowgirl Den in Calumet Township. Authorities allege he maintained a common nuisance and sold alcohol without a permit. The venue, which resembled a nightclub with bartenders, a dance floor, and a DJ, was found to be violating fire codes and lacked proper licenses for alcohol and tobacco sales. Despite being ordered closed, it briefly reopened after receiving an occupancy permit, but continued to operate unlawfully.
Hollingsworth has a history of legal troubles, including a 2022 conviction for animal cruelty related to his horse-riding protest and a 2024 jail sentence for battery and resisting law enforcement after another horse-riding incident. Police investigations into The Cowgirl Den revealed underage drinking, nude dancing, and unlicensed alcohol sales. An undercover officer purchased drinks at the club, and a subsequent search uncovered over 70 bottles of liquor and beer. Hollingsworth was arrested in June and is awaiting a hearing scheduled for July 8.
