“Dreadhead Cowboy” posts $4K to get out of jail after judge orders him into custody Thursday

Adam Hollingsworth, the man known as Chicago’s “Census Cowboy” and the “Dreadhead Cowboy,” turned himself in to authorities Thursday evening after a Cook County judge said he violated the terms of bail in a pending animal cruelty case by allegedly blocking traffic on the Dan Ryan Expressway last week. Hollingsworth quickly posted a $4,000 deposit bond with funds he said were raised from supporters after Judge Michael McHale ordered him into custody.

Meanwhile, video emerged overnight of an Illinois State Police officer being battered as he tried to arrest another man at last week’s blockade.

“Freeeeeee,” Hollingsworth posted on Facebook at 11:47 p.m. Thursday.

“Great,” a supporter responded. “now go sit your ass down and think of a safe and smart plan to bring awareness for our kids without putting yourself in them ppl face.”

Hollingsworth, 34, posted several Facebook Live videos Thursday evening as he solicited for bond money to be sent to his CashApp account and while he apparently drove to surrender at Cook County jail. Those videos no longer appeared on his social media page as of early Friday.

Illinois State Police troopers arrested Hollingsworth and four other people who allegedly blocked traffic on the outbound expressway near 47th Street around 3 p.m. on May 27. He streamed the shutdown on Facebook and said he hoped the disruption would increase awareness of gun violence in Chicago.

The arrest was a violation of bail in a pending animal cruelty case that Hollingsworth has been fighting since he rode a horse along the same expressway in September, McHale ruled Thursday.

Hollingsworth splashed onto the scene in a news conference last year during which Mayor Lori Lightfoot said he would be patrolling neighborhoods on horseback to drive up the city’s census response rate. But public opinion of Hollingsworth shifted after the September stunt when he allegedly forced one of his horses to gallop on the highway’s pavement until — according to prosecutors — it nearly died from exhaustion.

Early today, video emerged on social media that shows a State Police trooper being battered as he tried to detain one of the drivers who participated in last week’s highway shut-down.

Prosecutors last week said one of the men who was arrested with Hollingsworth, Gregory Sherman, is a 14-time convicted felon who has been to prison for gun violations, conspiracy to commit aggravated battery by firearm, five robberies, and multiple drug violations.

Sherman was charged with aggravated battery of a police officer in connection with the incident. Judge David Navarro last week set his bail at $25,000.

Hollingsworth, who is only charged with misdemeanor reckless conduct in connection with last week’s shutdown, is due back in court on the animal cruelty charge July 1.

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CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings. Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets. Our editorial email address is news@cwbchicago.com