Illegal Nightclub Operation Uncovered in Gary; Dreadhead Cowboy Arrested for Unlicensed Alcohol Sales
A months-long investigation into a makeshift nightclub in Gary culminated in a search warrant and arrest this past weekend, as authorities allege the business was illegally operating and selling alcohol without a license.
According to an affidavit filed by the Indiana State Excise Police, the establishment, known as The Cowgirl Den and located at 3985 Cleveland Street, was the subject of a citizen complaint in late 2024. What began as a tip led investigators into a deepening probe that exposed unlicensed alcohol sales, paid entertainment, and multiple code violations.
The business was first discovered during a fire inspection on Halloween night in 2024, when the Lake Ridge Volunteer Fire Department entered the premises and found a bar-style setup with dozens of patrons, alcohol on display, a live DJ, and dancers. The Assistant Fire Chief reported that the facility was operating like a nightclub without any required permits at that time. The business was ordered closed that evening for fire code violations but was allowed to reopen days later after an occupancy permit was issued listing Adam Hollingsworth as the operator.
However, the affidavit details that between November 2024 and June 2025, multiple pieces of evidence were collected indicating ongoing, unauthorized alcohol sales. Fliers circulated on social media advertised the business as “420 Friendly” and boasting a “full bar and hookah.” A drink menu obtained by investigators listed popular liquors including Don Julio, Hennessy, and Cosamigos, none of which could be legally sold at that address, according to records from the Indiana Alcohol & Tobacco Commission.
On June 14, 2025, undercover surveillance and a controlled operation led to confirmation of illegal sales. Gary Police, working with the Indiana State Excise Police, entered the club, paid a $20 cover, and was sold multiple mixed drinks by bartenders. Each drink cost $15 and, according to the Officer and clearly contained alcohol.
Later that night, a search warrant was executed. Investigators entered the establishment and documented a full bar operation, with dozens of opened and sealed bottles of liquor and beer. Two women were working as bartenders and told officers they were hired by Hollingsworth to serve drinks. Another man, confirmed he was asked by Hollingsworth to open the venue that night and even called Hollingsworth on the spot, who admitted over the phone to being the owner.
Adam Hollingsworth, who is also known as the “Dreadhead Cowboy” a figure previously in the public eye for a 2020 horseback-riding stunt on a Chicago expressway arrived on the scene during the search and identified himself as the business owner. He was taken into custody and, when confronted about the operation, reportedly asked officers, “Why am I being arrested for a private party with alcohol?”
Items recovered during the warrant execution included a binder listing Hollingsworth as the owner, drink menus, multiple bottles of liquor & beer, and a $20 bill that matched serial numbers recorded by police during the undercover operation.
As of Monday, Hollingsworth has been formally charged in Lake Superior Court with Maintaining a Common Nuisance (Level 6 Felony) and Unlawful Sale of Alcohol. No alcohol permit has ever been issued for 3985 Cleveland Street, according to state records.
