A nine-time convicted felon who was on felony bail for allegedly battering an Illinois State trooper during a protest that featured Chicago’s “Dreadhead Cowboy,” accidentally shot himself in the butt at a Bucktown gas station, and then lied about what happened, prosecutors said Thursday.
Gregory Sherman, 43, works 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,” his private defense attorney said.
Although the circumstances are unusual, Sherman is now the 31st person accused of killing or shooting someone—or attempting to kill or shoot someone—while on bail for a felony in Chicago this year.
On July 9, Sherman walked into St. Elizabeth Hospital after a bullet passed entirely through his left butt cheek and struck his right foot, Assistant State’s Attorney Steven Haamid 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.
But at the same time, other officers were responding to the Shell 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 a flash around Sherman’s back pocket area as he adjusted his pants while waiting in line.
After the flash, Sherman “jumped and then hobbled out of the gas station back to his vehicle,” Haamid said, adding that Sherman 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, he said, but investigators never found the gun.
Haamid said Sherman received four 10-year sentences in 2015 for robbing taxi drivers and was also convicted of robbing a taxi driver in 2006.
Also in 2006, Sherman was convicted of conspiracy to commit aggravated battery with a firearm. In that case, prosecutors alleged that he and two other inmates conspired to have a gun smuggled into the Cook County jail, where the group allowed themselves to be shot so they could sue the county.
On Thursday, prosecutors charged Sherman with Class X armed habitual criminal in connection with the gas station incident. Judge Charles Beach rejected the state’s request to hold Sherman without bail. Instead, Sherman must pay a $10,000 bail deposit to go home on electronic monitoring in the case.
But Sherman won’t be able to go home right away. Beach also ordered him held without bail for violating the bond conditions in the pending aggravated battery of a peace officer case, which is a story in itself.
In May 2021, Sherman, Adam “Dreadhead Cowboy” Hollingsworth, and three others were arrested after allegedly obstructing traffic on the Dan Ryan Expressway 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. A confrontation between troopers and members of Sherman’s anti-violence group, Ex-Cons for Community and Social Change, was captured on video:
The “not horrible” series
This report continues our coverage of individuals accused of killing, shooting, or trying to kill or shoot others while on bond for a pending felony case. CWBChicago began our series of reports in November 2019 after Cook County Chief Judge Timothy Evans publicly stated, “we haven’t had any horrible incidents occur” under the court’s bond reform initiative.
CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings.
Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets.
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