10 year sentence for ‘anti-violence worker’ who shot himself in the butt

CHICAGO — A 19-time convicted felon working as an anti-violence professional who shot himself in the butt inside a Bucktown gas station has been handed a ten-year prison sentence for possessing the firearm that wounded him.

Gregory Sherman, 45, served as his own attorney at times but was ultimately convicted of Class X armed habitual criminal during a jury trial this summer, according to court records. Following a series of post-trial motions, Judge Mary Brosnahan sentenced him this month.

On July 9, 2022, Sherman walked into St. Elizabeth Hospital after a bullet passed entirely through his left butt cheek and struck his right foot, prosecutors said. He allegedly told Chicago cops that he had been closing a dispensary in the 1500 block of North Milwaukee when there was a fight outside, and someone fired shots, striking him as he walked by.

Sherman later tried unsuccessfully to have his statements to police suppressed at trial because he was, he claimed, under the influence of prescription drugs.

While Sherman was speaking with officers, other cops responded to the Shell gas station at 1768 West Armitage because 911 callers reported that a man had run out of the business after shooting himself.

Surveillance video from the gas station allegedly showed Sherman standing in line when a flash erupted near his back pocket as he adjusted his pants.

Gregory Sherman | Chicago Police Department

After the flash, Sherman “jumped and then hobbled out of the gas station back to his vehicle,” a prosecutor claimed at Sherman’s bail hearing. Sherman allegedly stopped along the way to hand a “black object” to someone near the gas pumps.

Police found a shell casing on the gas station floor, but investigators never found a gun.

Although the circumstances were unusual, Sherman became the 31st person accused of killing or shooting someone while on bail for a felony in Chicago in 2022.

Sherman submitted a long list of reasons that he believed his conviction should be overturned, including Judge Brosnahan’s decision to strike one of the potential jurors: LeRoy K. Martin Jr., an Illinois appellate court justice and the former presiding judge of the Cook County Circuit Court criminal division.

Sherman must serve 85% of the ten-year sentence. He is currently scheduled to be paroled on Valentine’s Day 2031. That may change, though, because he is still fighting another felony case in which he is accused of battering an Illinois State Police trooper during a “protest” on the Dan Ryan Expressway in May 2021.

While working for the Ex-Cons for Community and Social Change in May 2021, Sherman, Adam “Dreadhead Cowboy” Hollingsworth, and three others were arrested after allegedly obstructing traffic on the Dan Ryan Expressway. They claimed it was a “protest” to raise awareness of violence against children.

Sherman is the only member of the group who was charged with a felony. Prosecutors said he battered a state trooper as they tried to clear the highway. The confrontation between troopers and members of ECCSC was captured on video:

Sherman’s previous felon convictions include four 10-year sentences for robbing taxi drivers in 2015. He was also convicted of robbing a taxi driver in 2006, a crime for which he received an 18-year sentence.

His defense attorney during his July 2022 bail hearing said Sherman worked full-time as an anti-violence worker, “out there on the street, trying to lower the criminal and dangerous issues that are going on in our community.”

Sherman’s other Illinois prison sentences, according to the Illinois Department of Corrections, include six years for being a felon in possession of a firearm in 2006, six years for aggravated unlawful use of a weapon in 2006, three years for conspiring to bring cannabis into a penal institution in 2003, three years for conspiracy to commit aggravated battery with a firearm in 2003, three years for being a felon in possession of a firearm in 2003, twelve years for armed robbery in 2003, three years for being a felon in possession of a firearm in 2003, three years for forgery in 2001, two years for theft in 1999, one year for possessing cannabis in 1999, two one-year sentences for possessing controlled substances in 1999 and 1997, and two three-year sentences for narcotics in 1997.

About Tim Hecke 374 Articles
Tim Hecke is CWBChicago's managing partner. He started his career at KMOX, the legendary news radio station in St. Louis. From there, he moved on to work at stations in Minneapolis, Chicago, and New York City. Tim went on to build syndicated radio news and content services that served every one of America's 100 largest radio markets. He became CWBChicago's managing partner in 2019. His email address is tim@cwbchicago.com