Traffic stops and starts along the busy Madison Street commercial strip on Chicago’s West Side.
Shoppers dip in and out of stores. Seagulls squawk and swarm in the hazy summer sky.
And then, just when it seems this Thursday afternoon could not possibly be more ordinary, a lone horseman appears in the White Castle parking lot, towering above passersby. He has a gentle smile, an easy command of his spirited steed, and red sequined stripes running down the sides of his jeans.
He’s Adam Hollingsworth, known to his growing fan base as the Dreadhead Cowboy. Even in a city full of spectacles, he draws stares as he makes his way up and down the street, sometimes cantering swiftly in an open traffic lane, sometimes pausing to chat with strangers.
Tween boys gape as they ride by on their sky-blue rental bikes: “It’s a (expletive) horse!”
A woman in leopard-print leggings speaks loudly into her phone: “We got a Black cowboy in front of Wiley’s Chicken & Ribs!”
Hollingsworth, 33, has attended a string of Black Lives Matter protests — on horseback — in recent weeks, braving tear gas and winning a large following with his equestrian skills and his commitment to the cause.
“That’s our Batman,” one Chicagoan tweeted.
Now he’s using his growing celebrity to promote horseback riding in largely Black neighborhoods of Chicago, answering questions on city streets, posing for photos, and offering starry-eyed children their first horseback rides.
His style is warm and playful, but his goal is ambitious.
“I want to put a barn in the inner city, so I can show kids in the inner city something different,” said Hollingsworth, who said he struggled with wrongful incarceration and a shooting injury before finding a new sense of purpose when his uncle Eddie Thomas introduced him to horses.
“If a horse can change my life, I know for a fact that it can change other people’s lives,” Hollingsworth said.
Hollingsworth grew up in a section of Woodlawn where gangs were prevalent. While he didn’t drink, smoke or participate in gang activity, he fought a lot and attended an alternative school, he said.
As a teen he was charged with, and convicted of, possession of a firearm. Hollingsworth said he hadn’t known about the gun, that the gun belonged to a friend who was riding in a car with him when police pulled them over. But, he said, he followed the rules of the street and didn’t snitch on his friend.
Not long after that, while he was still on probation for the gun charge, Hollingsworth was charged with possession of a stolen vehicle and served 18 months in the Cook County Jail. He said he was wrongfully charged and had nothing to do with the stolen car.
After that, it was hard to find a job, so Hollingsworth worked as a boxer and, until recently, as an exotic dancer.
In 2016 he faced a felony charge of gun possession, for which he served time. The gun wasn’t his, he said, but police blamed him. Then on Father’s Day of that year, Hollingsworth said, he was hit by a stray bullet while driving to a barbecue in Chicago, and the woman he was driving with was also injured. They both recovered, but doctors couldn’t remove the bullet from Hollingsworth’s chest, and he went through a tough time emotionally.
It was at that low point that his uncle Eddie Thomas, 60, who owns four horses in the south suburbs, offered him his first horseback ride. Hollingsworth, an animal lover who had never seen a horse in real life, said yes.
“It was, like, unbelievable,” Hollingsworth said. “I felt like I had power. It made me feel like I was the man, I was the boss. I even forgot that I got shot. It made me forget a lot. It was like therapy.”
Thomas has become a father figure and a daily presence in his nephew’s life, Hollingsworth said. At his uncle’s urging, Hollingsworth bought his first horse about a year ago and began trucking his mount in from the south suburbs so he could ride in neighborhoods like the one where he grew up.
Hollingsworth, the father of four children, ages 2 to 13, takes particular pleasure in giving children their first horseback ride. Kids line up for a turn, he said.
“Is this horse real?” they ask him. “Are you the police? Are you a cowboy?”
Sometimes, he said, he can’t get to all the kids who want rides: “It’s so heartbreaking. I wish I could just give them a horse.”
Often riding his best-known steed, a remarkably well-behaved chestnut-and-white paint horse named Prince, he has protested against police violence in Chicago and Cicero in recent weeks. “A lot of Black people have been getting killed, like our lives don’t matter,” he said. “We can’t just let it go. We want to be treated like any other race.”
Hollingsworth was temporarily blinded by tear gas while protesting in Minneapolis. In Berwyn, police cars surrounded him — but only to escort him safely to the protest site.
“Oh my God, I love them,” he said of Berwyn police. “They’re like, ‘Can we take a picture with y’all? We’re big fans.’”
At a protest in Chicago, he spent more than an hour on Facebook Live, frequently responding to questions from the public about whether he was riding a stolen police horse. No, he kept saying. He was riding his own horse. Finally, Hollingsworth allowed himself one passing joke: Yes, he said, he stole this horse from the cops.
The parody account Skipper Interactive released an incorrect tweet, for which it later apologized, saying “Protester stole a horse from police.” The tweet got 1.3 million views — and lots of pushback from local Dreadhead Cowboy fans.
Hollingsworth’s reputation grew when he visited the Little Village neighborhood June 2, after unconfirmed social media posts indicated that alleged Latino gang members were racially profiling and threatening Black people due to fears of looting. Rumors swirled, and Hollingsworth said he was very scared to visit.
“Thank you, queen,” Hollingsworth says when a woman in a tank top offers his horse a bucket of water.
“Ain’t nothing but love in Little Village,” a man with a red baseball cap tells Hollingsworth. “We Mexicans love everyone. We ain’t with all that (stupidity).”
In the video, Hollingsworth points out Black people walking freely on peaceful Little Village streets, and sympathizes with residents’ concerns about looting by protesters: “The Black and brown is together, man. They just don’t want nobody (destroying) their (stuff), and that’s how Blacks should be,” he says. “That’s how every race should be.”
During a phone interview in which his 2-year-old son played with a toy horse, Hollingsworth acknowledged that his current goal of a having a stable in Chicago is ambitious. Others have tried for decades to bring horseback riding to largely Black neighborhoods in a very segregated city.
Government budgets are stretched to the limit by COVID-19 and the ensuing economic downturn, but the Dreadhead Cowboy is undaunted, as is his mentor.
“If you follow your dream, anything is possible,” Thomas said.
Hollingsworth envisions a barn in the empty fields south of the University of Chicago, near 63rd Street and South Woodlawn Avenue, or maybe in Englewood. Asked how he will pay for his plan, he points to his GoFundMe page, which has raised more than $25,000.
He’s reached out to Ald. Jeanette B. Taylor’s office, he said, and has a meeting scheduled in July.
In the meantime, he has work to do. There are still so many people on Chicago streets who have never seen a horse in real life, and so many children who haven’t yet had the chance to get on and ride.