Adam Hollingsworth, also known as the Dreadhead Cowboy and the Census Cowboy, was arrested again Thursday evening after he helped block traffic on the Dan Ryan Expressway. While chatting on Facebook Live around 3 p.m., Hollingsworth used his truck to help block the expressway’s outbound lanes near 47th Street. Dressed in a black Death Row Records jacket and a black cowboy hat, Hollingsworth said he wanted the blockade to increase awareness of gun violence in Chicago.
Prosecutors 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.
“We’re shutting her down, y’all, once again,” Hollingsworth said as he began his Facebook video Thursday. “It’s happening again…this Dan Ryan shut down part two!”
“We’re losing too much. We lost a good brother, Vee,” he continued, referring to widely-admired youth dance coach Verndall Smith, who was killed in a drive-by shooting this month.
“A kid just got shot on 95th,” Hollingsworth says later, leaning out the driver’s window of a pick-up truck.
“Just now?” a woman asks.
“Yeah,” Hollingsworth answers, apparently referring to the shooting of a 7-year-old boy and a 28-year-old man who were shot inside a car on the 1700 block of East 95th around 2:54 p.m. Police later said the boy suffered a graze wound to his ear and the man was shot in the chin.
Later, two Illinois State Police troopers order Hollingsworth out of his truck. He was subsequently arrested along with Sherman, another man, and two women, who are all between 41- and 50-years-old, according to police. Police charged him with misdemeanor reckless conduct and sent him home.
Sherman is charged with aggravated battery of a police officer in connection with Thursday’s incident. Judge David Navarro set his bail at $25,000. Sherman will need to post a 10% deposit to get out of jail.
Hollingsworth splashed onto the scene in a mayoral news conference last year in 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 in September after he allegedly forced one of his horses to gallop in the Dan Ryan Expressway’s traffic lanes until — according to prosecutors — the animal nearly died of exhaustion.
Facing one felony count of aggravated animal cruelty, Hollingsworth ditched his attorneys months ago and has been serving as his own lawyer during court appearances. On March 9, Judge Michael McHale questioned Hollingsworth about Facebook posts that indicated he might be taking a trip to Las Vegas or be around horses again, activities that are prohibited while he awaits trial. Hollingsworth said the posts weren’t true, saying he made them to get a reaction from prosecutors.
In another Facebook post that McHale heard about, Hollingsworth mentioned the prosecutor on his case, Christina Dracopoulos, by name and gave her the finger. “Christina, f*ck you,” the budding barrister said.
McHale threatened to hold Hollingsworth in contempt of court if he posted false information or other “unprofessional” videos while the case is pending.
On April 30, McHale made note of a court filing Hollingsworth made.
“You raise issues about taxes. About contracts. Treason and sedition. Treaties between countries, federally funded highways, licensing issues, [and] whether or not you need a permit to protest on a highway,” McHale said.
“You are charged with one count of aggravated cruelty to animals,” the judge continued, calling Hollingsworth’s filing “completely irrelevant.”
Later, Hollingsworth asked McHale to clarify what kinds of animals the court has barred him from being near.
“Is it — horses is the only animals that I can’t be around?” Hollingsworth inquires.
“Right,” McHale confirmed. “I didn’t say any other animals. Right. Just horse…”
“Other farm animals? I’m allowed to be around them?”
Prosecutor Dracopoulos could be seen bravely biting her lip in an effort to contain her laughter.
“Yes, you are. Yeah. I said no horses. So. Dogs, cats, goats, pigs, yeah…”
“Donkeys?” Hollingsworth asked. “Mules?”
“Mmm, Mister— I guess they aren’t technically horses,” McHale agreed as Dracopoulso covered her mouth with her hand and began shaking with laughter.
“You’re right sir,” the judge agreed. “Ok. Sure. Just no horses.”
“Ok.”
“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 on the Zoom call — seated in the Cook County Jail — rocks back and forth in laughter, shaking his head.
“Right. I just wanted to make that clear.”
Hollingsworth is due back in court on the animal cruelty charge July 1.
