Dreadhead Cowboy gets 1 year sentence for riding horse to exhaustion during expressway ‘protest’

Adam “Dreadhead Cowboy” Hollingsworth pleaded guilty to one count of felony animal cruelty Friday, bringing a sudden end to a 16-month saga that began when he rode a horse on the Dan Ryan Expressway, nearly resulting in the animal’s death from exhaustion, according to prosecutors.

Judge Michael McHale sentenced him to one year in prison, but also gave Hollingsworth credit for 232 days he spent on electronic monitoring while the case was pending. Hollingsworth is not expected to serve any prison time after receiving the state’s standard 50% “good behavior” sentence reduction.

In September 2020, two months after the city contracted with Hollingsworth to drum up participation in the decennial census as Mayor Lori Lightfoot’s “Census Cowboy,” the 34-year-old took his newfound fame and one of his horses on the road — literally.

Adam Hollingsworth rides his horse, NuNu, on the Dan Ryan Expressway in September 2020. | CPD; Facebook

Police arrested Hollingsworth after he live-streamed his 7-mile ride up the expressway while allegedly whipping and kicking his horse, NuNu, to keep it going. Hollingsworth said his stunt was a “kids lives matter” protest.

Two veterinarians who later examined the horse said it “suffered greatly, bled profusely,” collapsed repeatedly, and was not correctly saddled and cushioned, a prosecutor said during Hollingsworth’s initial bond hearing. One veterinarian reportedly told investigators that NuNu’s treatment was equivalent to “making an 80-year-old woman run a full marathon.”

Hollingsworth vigorously denied mistreating the horse.

For the next sixteen months, Hollingsworth hired and fired two attorneys, then served as his own lawyer. His lack of training as a barrister sparked many awkward moments.

A motion to dismiss Hollingsworth filed on his own behalf last August was just five words long: “My constitutional right was violated.”

During one hearing, Hollingsworth and McHale went back and forth about exactly which farm animals Hollingsworth was prohibited from being near.

“Is it — horses is the only animals that I can’t be around?” Hollingsworth inquired.

“Right,” McHale confirmed. “I didn’t say any other animals. Right. Just horse…”

“Other farm animals? I’m allowed to be around them?”

“Yes, you are. Yeah. I said no horses. So. Dogs, cats, goats, pigs, yeah…”

“Donkeys?” Hollingsworth asked. “Mules?”

“I really don’t want to get into splitting hairs about donkeys and mules and burros and anything else, Ok. So, please just behave wisely…No HORSES.”

“Yes, sir,” Hollingsworth acknowledged.

“No ponies, either,” McHale warned.

“I know. A pony is a horse,” Hollingsworth agreed as another defendant awaiting their turn the Zoom call — seated in the Cook County Jail — rocked back and forth in laughter, shaking his head.

The novelty of Hollingsworth’s amateur lawyering wore off and McHale ran out of patience when Hollingsworth showed up unprepared for trial.

The final straw for McHale was Hollingsworth’s preposterous claim that he didn’t have prosecutors’ evidence against him because his dog ate the flash drive. McHale sentenced him to 90 days in jail for contempt.

Records in the animal cruelty case’s court file include a “horse bill of sale” that shows Hollingsworth sold one of his other horses, a 14-year-old Quarter Horse named “Prince,” for $1,500 cash two days after he was arrested on the Dan Ryan.

In an affidavit of assets and liabilities filed last August, Hollingsworth said he paid $1,000 a month in child support, received Link benefits, was trying to get a job as a tire shop delivery person, and owned a 2018 Jaguar.

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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