Chicago City Wire

The contract was signed on July 10, 2020, between World Business Chicago (WBC), the city's “economic development agency,” and Adam Hollingsworth.

According to Chicago Police records, Hollingsworth has been arrested nine times since 2014. In 2016, he served jail time for a felony gun possession charge. 

He was also arrested for domestic battery in Will County in September 2019.

Mugshot of Hollingsworth

Hollingsworth faces a jury trial on Nov. 24, according to the Will County Clerk.

A July 6 Chicago Tribune profile of Hollingsworth reported that he has worked most recently as a boxer and exotic dancer. He is paid $1,000 per day under the contract with WBC. 

“You will be out riding for five days total, which will be determined by the census team and weather permitting,” the contract reads. “Days determined are July 13 through July 21, 2020.”

The contract includes a confidentiality clause that prevents Hollingsworth from disclosing the terms of the agreement.

Hollingsworth, 33, drew the attention of Chicago Mayor Lori Lightfoot after he attended a series of South Side Black Lives Matter protests on horseback in June and July. The contract specifically calls for a ride with Lightfoot. 

“In addition to the ride time, you and your horse will participate in an event with the mayor on Monday, July 13,” the contract reads. “We would like you to arrive at 9 a.m., most likely with you riding in on your horse.” 

Hollingsworth also grants the City of Chicago a release and promises not to sue over any incident that occurs during the performance of his services. The city contract makes clear that Hollingsworth himself is responsible for his horse's injuries. 

“Contractor shall hold harmless any acts and/or injuries to the contractor’s horse,” it states. “WBC is not responsible for anything related to the contractor’s horse.” 

He is also allowed to submit expenses. 

Hollingsworth was central to the city's 2020 Census marketing strategy in South and West Side neighborhoods. 

“You serve as a census ambassador, encouraging people to fill out the census on the South and West Sides of the city, acting in a professional manner at all times and staying on topic with the messaging of the census,” the contract reads. “No one other than the contractor can ride the horse.”

A census marketing document includes a slide dedicated to the “Census Cowboy” and lists East Garfield Park, West Garfield Park, Washington Park, Woodlawn. Englewood, Greater Grand Crossing, North Lawndale, South Lawndale/Little Village, Back of the Yards and West Englewood as his target neighborhoods.