‘Dreadhead Cowboy' accused of running illegal bar in unincorporated Gary

Chicago Tribune

19-06-2025

A Chicago man who gained notoriety for riding a horse on the Dan Ryan Expressway was charged with setting up an illegal bar and strip club in Calumet Township.
Adam Hollingsworth, 37, is charged with maintaining a common nuisance, a Level 6 felony, and misdemeanor selling alcohol without a permit, according to the probable cause affidavit.
In October, Indiana State Excise Police received a complaint about The Cowgirl Den, located at 3985 Cleveland St. On Nov. 1, the Lake County Sheriff's Department arrested an individual at the location for public intoxication, court records state.
Police interviewed Lake Ridge Volunteer Fire Department Assistant Chief Dennis Carlotto, who said that the department is tasked with issuing occupancy permits for businesses in their fire district. He requested assistance from the Lake County Sheriff's Department when they made a fire inspection of the business on Oct. 31, records state.
Dozens of people were present. Carlotto said the interior resembled a nightclub, with a counter staffed by bartenders and stocked with alcoholic beverages, a dance floor and a DJ. He said Hollingsworth identified himself as the operator of the business, the affidavit states. Carlotto told him that the business was ordered closed due to violations of state fire code. The business was granted an occupancy permit the next week and allowed to reopen, court records state.
Police received photos of the Cowgirl Den's drink menu and fliers for events, saying it's '420 Friendly, Full bar and Hookah'.
In searching its records, the Indiana Alcohol Tobacco Commission found no evidence indicating the address had a valid alcohol license or had a valid permit to sell tobacco products, records state. As of June 16, there are no signs of Hollingsworth applying for a license or permit.
Hollingsworth advertised the Cowgirl Den under his 'Dread Head Cowboy' Facebook page. The nickname originated from a September 2020 incident where he rode his horse NuNu seven miles without horseshoes on the Dan Ryan Expressway to protest gun violence against children, according to Chicago Tribune archives. He later faced animal cruelty charges as the horse collapsed on the pavement near 95th Street and was overheated, bleeding from the hooves, and had dilated eyes.
He pleaded guilty to animal cruelty and was sentenced to one year in prison in January 2022, court records state.
He was also arrested in Hammond in May 2023 after police caught him riding his horse in the 7000 block of Indianapolis Boulevard, court records state. Police tried to prevent him from getting back on his horse again and Hollingsworth hit one of the officers with his elbow, resulting in battery of a police officer, resisting law enforcement and disorderly conduct charges. A jury found him guilty on the battery and resisting charges in May 2024, and he was sentenced to 30 days in jail, records state.
In January, there was a domestic disturbance call at the Cowgirl Den, and when police responded, Hollingsworth informed them that he had paid dancers performing inside.
Individuals were seen drinking alcohol, the affidavit states. In April, a video was sent to police that showed a nude woman dancing inside the club, with nearby patrons drinking alcohol.
An undercover Gary Police officer went to the club on June 14 and requested a tequila drink and he later ordered another drink, records state. Officers later executed a search warrant that turned up a beverage menu and more than 70 bottles of liquor and beer.
Hollingsworth was arrested at that time and said, 'Why am I being arrested for a private party with alcohol?' court records state. He has since posted a $1,495 bond and his initial hearing is scheduled for July 8.