Hollingsworth's bail was set at $25,000.
At around 5:30 p.m. Hollingsworth left jail with his wife and friends, but made no comment.
In court a prosecutor told the judge, that Hollingsworth whipped the horse when it slowed and it was injured from an ill-fitting saddle and running miles on concrete.
The prosecutor told the court the horse was extremely dehydrated, overheated, suffered cuts and sores and is now in critical condition.
The horse can never be ridden again and may be euthanized, the prosecutor said.
Hollingsworth is facing several charges including reckless conduct, disobeying a police officer and trespassing on the expressway, obstruction of traffic by a person, pedestrian on a controlled access highway and operating a non-highway vehicle on a highway. The Cook County State's Attorney's Office approved one additional felony count of aggravated animal cruelty Tuesday evening.
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The public defender noted Hollingsworth's work as an activist, but the judge said treatment of the horse has nothing to do with protest.
Hollingsworth is expected to appear again in court on Sept. 30.
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His sister said he remains in jail Tuesday, and the family is still waiting for details from authorities.
"He wasn't disturbing the peace. He wasn't hurting nobody," Lateshia Hollingsworth said. "It's very frustrating to even walk into a Chicago police station and they just have this nasty attitude and you're just trying to find information on your brother."
The calls started coming in just before 4:30 p.m. Monday. Hollingsworth was going live on social media with a message.
"Kids lives matter. Until kids lives matter, until we understand kids lives matter, nothing else matter," he said on Facebook Live.
In another post earlier on his Facebook page he wrote, "we focus on kids lives matter this gone keep happening" and told his followers he was going live at 4 p.m., saying, "y'all don't wanna miss this I promise."
Hollingsworth and his supporters said the ride was meant to get the public and politicians' attention to children's needs in the city. They say funding for children's programs, especially in low-income areas, is far from adequate and there is also not enough investment in those communities.