In late May, as protests against police brutality began to seize American cities, videos of a Black man on horseback wearing a bulletproof vest spread widely on social media. In many of the posts, users suggested that he had stolen a policeman’s horse.
But Adam Hollingsworth, a 33-year-old Chicagoan, is no thief. The horse in the video, Prince, is one of four he owns and rides around the city, where he is known as the Dreadhead Cowboy.
You have to have “some kind of experience to get on a horse to ride it,” he said in a phone interview last week. And, he added, “if you steal a police horse, it’s like kidnapping a police officer. You can’t just get up and steal a police horse.”
As the false accusations piled up, Mr. Hollingsworth said his car was vandalized and that he received death threats. The experience hammered home for him that his reason for riding — to expand people’s ideas about Black masculinity and to promote a message of unity in some of Chicago’s most racially segregated neighborhoods — remains urgent.
“It’s not just about me,” he said. “Everything I’m doing is for the future.”
Mr. Hollingsworth was born and raised in Woodlawn, a majority-Black neighborhood (nearly 83 percent, according to a 2019 analysis by the Chicago Metropolitan Agency for Planning) on the South Side of Chicago. The area has recently appeared in the news as the proposed site of the Obama Presidential Center.
Horseback riding didn’t come into Mr. Hollingsworth’s life until adulthood, once he was released from prison after a wrongful conviction for gun possession.
“I don’t play with guns,” Mr. Hollingsworth said. “I’m not that kind of guy.” But when his car was pulled over in 2006, someone riding with him did have a gun, which the police found when they searched the car. The officers asked for the ages of the men in the vehicle.
“I was 19, and they said, ‘You’re the oldest, it’s your gun.’”
The bail for his release was set at $5,000. Unable to pay, Mr. Hollingsworth sat in jail awaiting a court date. His public defender advised him to fight the charge, believing there was insufficient evidence to convict him. However, after a month in a cell, Mr. Hollingsworth said he just wanted to go home and requested his public defender arrange for a plea deal. After serving one month in Cook County Jail, he pleaded guilty and was released on probation.
Upon his release, Mr. Hollingsworth focused on staying out of trouble and finding a job. But with a criminal record, this became a herculean task. He began working as an exotic dancer in 2010 and bought his first horse, Wi-Fi, nine years later for $800 during a period of severe depression.
“My horse was my therapy,” he said. Over time, one horse became four. He keeps them in a barn at his uncle’s house in Crete, a suburb of Chicago, and brings them out to the city almost every day, as long as the weather cooperates.
“When this pandemic came about and everyone was depressed and miserable, I thought maybe they can help them too,” he said.
During lockdown, Mr. Hollingsworth began riding around Chicago’s Black and Latino communities to bring joy to residents, especially young children. “I didn’t have my father in my life,” he said. “To have a kid say I’m their hero, it melts my heart.” His son, Akil, 12, has begun referring to himself as the Dreadhead Cowboy Jr. Some adults have told him it is their first time seeing a horse in real life.
“You’ve never seen a horse in the hood,” he said.
He said it was not unusual for onlookers to question his ownership of the horses. “When people see me on a horse, they always ask if I’m a police officer. They ask if I got money. If I steal it. How I get it,” he said.
“You could be the brokest guy in the world, but you pull up on a horse in a Black community and everyone thinks you’re rich,” he added.
The fallout from the viral posts about him and Prince left him scared and concerned about how quickly bad information travels online. “People be sharing posts and not be doing their own investigations,” he said. “The first time I see something, I do research.”
But he is also harnessing his growing fame to give back to his community. “I’m trying to put a barn in the city,” he said, specifically in Woodlawn. Already he has raised more than half of his $50,000 goal on GoFundMe.
As for the virus, he’s not afraid. He has been taking all the recommended precautions.
“I’m social distancing being on top of the horse,” he said. “Being a Black man, I’m taking a chance every day by stepping outside.”
