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‘Dread Head Cowboy’ sentenced to 90 days in jail on contempt charge for sparring with judge

Activist Adam Hollingsworth, who is representing himself against animal cruelty charges, was led out of court after repeatedly interrupting Cook County Judge Michael McHale.

Adam Hollingsworth, otherwise known as “The Dread Head Cowboy,” speaks to reporters after a court hearing in September 2020. Hollingsworth, who was supposed to stand trial this week on animal cruelty charges, was jailed Tuesday on a contempt of court charge after repeatedly interrupting the judge in his case and accusing prosecutors of withholding evidence.
Adam Hollingsworth, otherwise known as “The Dread Head Cowboy,” speaks to reporters after a court hearing in September 2020. Hollingsworth, who was supposed to stand trial this week on animal cruelty charges, was jailed Tuesday on a contempt of court charge after repeatedly interrupting the judge in his case and accusing prosecutors of withholding evidence.
Ashlee Rezin/Sun-Times file photo

Adam Hollingsworth, the activist known as the “Dread Head Cowboy,” was sentenced Tuesday to 90 days in jail on a contempt charge for arguing with a Cook County judge.

The contempt charge came a day after Hollingsworth, who is representing himself in his animal cruelty case, had repeatedly talked over Judge Michael McHale and made claims that prosecutors were holding back evidence.

Hollingsworth was led out of the courtroom by sheriff’s deputies to the holding cell in McHale’s chambers, leaving his black Stetson on a table. After an hour in chambers, McHale recalled the case and handed Hollingsworth the 90-day sentence.

“You have made a mockery of these proceedings,” McHale said after rattling off a series of incidents where Hollingsworth had made unsubstantiated claims or disrupted court since he was arrested for the horseback ride he took in 2020 on the Dan Ryan Expressway to raise awareness about violence against youth.

“You have tried to do that, and you’ve succeeded.”

At the end of a status hearing Monday, McHale ordered Hollingsworth to return to court with a flash drive prosecutors had turned over to him.

Tuesday, Hollingsworth claimed a dog ate the flash drive and repeatedly interrupted the judge.

“We are not going to do this the way we’ve been doing it the past year and a half,” McHale had warned Hollingsworth, telling him he’d be held in contempt of court if he interrupted him three times.

After sparring with Hollingsworth the previous day, the judge quickly grew exasperated again Tuesday as Hollingsworth, 34, repeated claims he had not received discovery materials, including audio from a dashboard camera that prosecutors said they did not have.

“Where’s the flash drive?” McHale asked.

“My dog chewed it up,” Hollingsworth said, prompting the judge to order the activist to raise his right hand and swear to tell the truth.

“Did you throw it out? And, by the way, lying under oath is a crime. It’s perjury,” McHale said.

McHale’s temper flared as Hollingsworth claimed that prosecutors had been hiding evidence from him.

Assistant State’s Attorney Christina Dracopoulos said prosecutors had turned over all files in the case to Hollingsworth on “several” occasions and had sent him an online link to the same files Monday. Hollingsworth conceded he had not downloaded those files.

“I want to know from you what right do you have, what basis do you have, to make that claim against the prosecutors,” McHale said. “You’re saying you got (the files), you got it yesterday. Would you still like to make an accusation they are hiding evidence, or would you like to withdraw it?”

As Hollingsworth stood silent for several seconds, the judge began speaking.

“I guess you’re thinking, because ...”

“Can I talk?” Hollingsworth interjected, talking over the judge.

“That’s it! You’re in contempt! Take him back,” McHale said.

Hollingsworth has struggled to navigate the court system since he publicly fired his pro-bono defense attorney in October 2020. His lack of knowledge of court procedures has continually been on display in McHale’s courtroom since he started representing himself.

McHale said Hollingsworth would get day-for-day credit for his 90-day sentence.

The judge set the next hearing for the case on Jan. 21.