“Dreadhead Cowboy” Busted: Inside Gary’s Illegal Nightclub Operation ? By GerryPthaDJ

A months‑long undercover probe has culminated in what authorities are calling the shutdown of a rogue nightclub in Gary, Indiana—and the arrest of its flamboyant operator, better known to some as the “Dreadhead Cowboy.”

The Rise and Fall of “The Cowgirl Den”

• Late 2024 tip-off: A citizen complaint first alerted state excise and fire officials to a makeshift nightclub illegally operating out of 3985 Cleveland Street—advertised on social media as “420 friendly” with a “full bar and hookah”  .
• Halloween 2024 inspection: Lake Ridge Volunteer Fire Department officers, responding to a routine fire inspection, discovered a packed bar with live DJs and dancers—despite the absence of proper permits. The venue was ordered shut for smoke and occupancy violations. Amazingly, it reopened days later under an occupancy permit issued to Adam Hollingsworth  .

Undercover Sting & Arrest

• November 2024–June 2025: Investigators tracked ongoing illicit alcohol sales—secret drink menus featuring Don Julio, Hennessy, and Cosmos, along with social media flier posts supporting illicit activity—all lacking a valid license from the Indiana Alcohol & Tobacco Commission  .
• June 14, 2025 raid: Undercover officers entered The Cowgirl Den with a $20 cover charge. Each were served $15 mixed drinks—clearly containing alcohol. Based on this evidence, a search warrant was executed later that night  .
• The bust: Authorities found dozens of bottles, bartending staff ready on duty, and a binder listing Hollingsworth as owner. When confronted, Hollingsworth—arriving on‑site—reportedly asked: “Why am I being arrested for a private party with alcohol?”  .

Who Is Adam Hollingsworth?

Adam Hollingsworth, 38, of Ford Heights—who gained notoriety in 2020 as the “Dreadhead Cowboy” after riding his horse down Chicago’s Dan Ryan Expressway—has once again found himself in the spotlight, this time for alleged felony crimes. He’s now facing charges of:

• Maintaining a Common Nuisance (Level 6 Felony)
• Unlawful Sale of Alcohol  

State records confirm that at no point was an alcohol permit ever issued for the Cleveland Street address.

What Could This Mean?

• Serious legal consequences: Each charge carries potential jail time and stiff fines. Level 6 felonies, while the lowest class of felony, remain serious offenses.
• Public safety implications: Beyond unlicensed sales, the club reportedly operated in violation of fire and occupancy codes—creating hazardous conditions for patrons.
• Broader impact: This crackdown serves as a cautionary tale to other pop‑up nightlife venues that skirt regulations.

Bottom Line

From a citizen tip to an undercover sting operation, the unraveling of “The Cowgirl Den” highlights how grassroots vigilance—and coordinated enforcement—can expose hidden dangers in unregulated entertainment spaces. With Hollingsworth now behind bars and facing formal charges, the chapter closes—for now—on Gary’s most colorful rogue nightclub.