Dreadhead Cowboy Sentenced To 90 Days In Jail For Contempt

CHICAGO — Adam Hollingsworth, Chicago’s Dreadhead Cowboy, was taken into custody Tuesday and sentenced to 90 days in jail after his excuse for not following a court order did not go over well with a Cook County judge he continued to interrupt during a hearing.

The order states that Hollingsworth has repeatedly made misrepresentations to the court, showed disrespect to opposing counsel and has interrupted the court despite being warned. That landed him in the Cook County Jail for 90 days, according to an order issued Tuesday afternoon.

On Tuesday, Hollingsworth told Judge Michael McHale that his dog had chewed up the flash drive that prosecutors had provided him that included files used as evidence in the animal cruelty charges Hollingsworth faces, the Chicago Sun-Times reported.

Hollingsworth has repeatedly drawn the ire of McHale, who is overseeing the proceedings in which Hollingsworth is representing himself. Hollingsworth faces the animal cruelty charges stemming from an incident in 2020 when he rode a horse down the Dan Ryan Expressway to bring awareness to children being abused in Chicago.

On Monday, McHale ordered Hollingsworth to bring the flash drive with him to court. On Tuesday, when asked where the flash drive was, Hollingsworth told the judge that his dog had chewed it up. He was then ordered to hold up his right hand and swear to tell the truth, according to the Sun-Times.

As Hollingsworth, 34, continued to interrupt the judge, McHale warned him that he would be held in contempt of court if he continued to disrupt the proceedings. He also said he would be guilty of perjury if he lied about the whereabouts of the drive that contained materials provided to Hollingsworth by prosecutors.

“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, according to the Sun-Times “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?”

Hollingsworth did not answer and when McHale suggested he must be thinking because he did not answer, Hollingsworth cut the judge off in mid-sentence and asked to speak, the Sun-Times reported.

“That’s it, you’re in contempt,” McHale said, ordering deputies to take Hollingsworth into custody.

McHale later ordered jail time for Hollingsworth, who has struggled to represent himself ever since he fired his court-appointed attorney and decided he would serve as his own lawyer. In the court order, officials said that despite being told that communications would proceed in a "much more focused, efficient and respectful" manner than they had in the past, Hollingsworth continued to interrupt the court.

Hollingsworth also gave "evasive answers" to direct questions in an effort to distract, confuse and delay the court, the order states. Hollingsworth was warned about the penalty for contempt, which can be up to six months in jail and/or a $500 fine and yet, Hollingsworth continued his behavior, which led to McHale's order.