How Adam Hollingsworth, Chicago’s Dread Head Cowboy, became an agent of change

Adam Hollingsworth, 33, otherwise known as “The Dread Head Cowboy,” greets a Chicago Police officer as he rides his horse Prince in the Loop, Tuesday afternoon, June 16, 2020. | Ashlee Rezin Garcia/Sun-Times

Across Chicago, people hear Woodlawn native Adam Hollingsworth before they see him — or rather, they hear the clip-clop of his horse Prince’s hooves on the asphalt.

Thanks to his impromptu visits on horseback to neighborhoods all over the city, and the social media attention they generate, the 33-year-old former boxer is better known to many as the “Dread Head Cowboy.”

Hollingsworth bought his first horse in 2016 and now owns three — Prince, Bella and Unity, who live at his uncle’s ranch in Crete. He’s always found it therapeutic to be around horses and wanted to spread that message to kids and adults in communities across Chicago, many of whom, he says, have never seen a horse in person before.

But when he saddled up Bella on Saturday, May 30, it wasn’t for another simple meet and greet — it was to join a planned protest in the Loop over the death of George Floyd in Minneapolis.

Calm amid chaos

Hollingsworth was shaken when he saw the video of Floyd crying out that he couldn’t breathe during his arrest. That could have been him, he thought, or someone he cared about.

“That was my brother. That was my mother. That was my sister. That was me down there. That could have been me,” he said. Watching the video, “it hurt.”

The lifelong Chicagoan has had his own run-ins with police in the past. Last year, he says he was stopped by police seven times — and ticketed once — while riding his horses in the city. (A judge later tossed the ticket, Hollingsworth said.)

Adam Hollingsworth, 33, otherwise known as “The Dread Head Cowboy,” rides his horse Prince in the Loop, Tuesday afternoon, June 16, 2020.

Still, Hollingsworth said he has a positive relationship with many police officers he encounters on his frequent rides. “We have a lot of good cops,” he said. “We have a lot, even though we see a lot of people giving them hell, and they do the best they can in that situation.”

When the initially peaceful Loop protest May 30 turned violent as looters raided storefronts and clashed with police, Hollingsworth said his first instinct was to leave.

“I’m not out here for looting and rioting,” he said. “I’m out here trying to bring positive back.”

But he soon realized he could use his visibility to help — both at the scene and online, where he had been streaming the unfolding events on Facebook Live.

“I know for a fact I saved a lot of people from getting hurt that day because they were behind me following me everywhere I was going,” he said.

After hearing gunshots, Hollingsworth found a man who had been shot in an alley and tracked down a police officer to get the man some help.

The view from above

That day, Hollingsworth says, something clicked. He knew he stood out amid the chaos in his cowboy hat, riding Bella through the Loop, and that his reputation as a community-builder lent credence to his peacekeeping efforts at a time when tensions were high.

In the days following the protest and looting, rumors of rising racial tensions among Latinos and African Americans in Little Village stirred conflict in the neighborhood. Residents, including some gang members, tried to guard local businesses against looting, and there were reports of African Americans being targeted while walking in the neighborhood.

Having ridden Prince in Little Village before, Hollingsworth said he received messages from Latino friends and strangers on June 2 asking him to come and show his followers what was really happening.

“When I was in my car on the way over there, I was scared,” said Hollingsworth, who lives in Englewood. “But as I put on my vest, my cowboy hat and my cowboy boots, I started to feel more relaxed.”

As he and Prince settled into their ride, Hollingsworth led them off 26th Street and down side streets, all while streaming on Facebook Live. People stopped to say hello and snap photos, and one woman even put out a bowl of water for Prince.

“Theres nothing but love here. It’s not what y’all think it is,” Hollingsworth told his viewers over and over again.

The next day, Latino and African American residents held a march supporting solidarity between their communities, and some cited Hollingsworth’s videos as having helped quell the fear online.

Hero on horseback

Now when Hollingsworth passes cops on his horses, they tell him they’re fans. People have told him he’s making a difference — and he’s not done yet.

Hollingsworth continues to peacefully protest, most recently at President Trump’s Oklahoma rally, and he’s trying to raise $50,000 on GoFundMe to continue visiting Chicago neighborhoods and other Midwestern cities. The funds will be used for gas, food for his horses, cleaning supplies, trailer maintenance and other expenses related to the upkeep of the horses, and Hollingsworth hopes to keep inspiring inner-city kids on his tour.

“I feel like I have a lot of people looking up to me and watching,” Hollingsworth said. “I don’t want to let anybody down.”