#31: Anti-violence worker, who’s also a 9-time felon, shot himself in the butt at a Bucktown gas station while on felony bail, prosecutors say

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.

Gregory Sherman | CPD

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.

The actual number of murders and shootings committed by people on felony bail is undoubtedly much higher than the numbers seen here. Since 2017, CPD has brought charges in less than 5% of non-fatal shootings and 33% of murders, according to the city’s data. 

You can support CWBChicago’s work by becoming a subscriber today.

#1: Man who tried to shoot 3 outside a North Side restaurant on New Year’s Day had a pending felony case, prosecutors say (January 6, 2022)

#2: Felon awaiting trial for 4 sexual assault cases escaped from electronic monitoring and tried to kill investigators who tracked him down, prosecutors say (January 15, 2022)

#3: With felony gun case pending, man shot passerby during “exchange of gunfire,” prosecutors say (January 23, 2022)

#4: Seven-time felon on electronic monitoring for his 4th gun case tried to shoot and kill his girlfriend’s father, prosecutors say (January 26, 2022)

#5: Teen on electronic monitoring for TWO gun cases carjacked a Lyft driver, then shot a 15-year-old at point-blank range, prosecutors say (February 10, 2022)

#6: Man killed nursing student months after going AWOL from felony DUI case, prosecutors say (February 20, 2022)

#7: Man shot and killed his own brother while on bail for a felony gun case, prosecutors say (February 22, 2022)

#8: Beloved Hyde Park bartender was killed by a robber who has 3 pending felony cases, prosecutors said (March 7, 2022)

#9: Man involved in New Year’s shoot-out that left one dead was on bail for his 3rd gun felony, prosecutors say (March 8, 2022)

#10: An 11-time convicted felon shot a 3-year-old and tried to kill the boy’s mother while on felony bail, prosecutors say (March 11, 2022)

#11: Man allegedly stabbed another to death 4 days after getting released on felony bail (March 29, 2022)

#12: He opened fire on his ex’s house, killing a man, prosecutors say. But he was supposed to be home 24/7 for a pending felony gun case. (March 29, 2022)

#13: Man shot a woman, fired toward 4 others, while on bond for being a felon in possession of a firearm, prosecutors say (April 7, 2022)

#14: Man killed his parents in an Uptown senior center while on bond for federal armed robbery and gun charges, prosecutors say (April 14. 2022)

#15: Four-time felon opened fire on a carload of victims, injuring 2 while on bond for felony gun case, prosecutors say (April 20, 2022)

#16: Man shot his ex this month and her boyfriend last month, prosecutors say. He was on felony bail. (April 24, 2022)

#17: Man tried to kill 2 cable TV installers over a missing dog, prosecutors say. He was on bail at the time. (April 30, 2022)

#18: Man escaped from electronic monitoring and ran over a cop in a stolen car while fleeing a murder scene, prosecutors say (May 19, 2022)

#19: A two-time felon circled a West Side neighborhood for 15 minutes looking for someone to kill in a revenge murder, prosecutors say. He was on bond for a gun case at the time. (May 21, 2022)

#20: Alleged mass shooter had a felony gun case pending when he killed 2, wounded 7 near Magnificent Mile, records show (May 22, 2022)

#21: Five months after escaping from electronic monitoring, he helped shoot up a carload of people, injuring 2, prosecutors say (May 29, 2022)

#22: Man accused of setting ‘Walking Man’ on fire has been AWOL from 2 felony cases for 15 months, court records show (May 30, 2022)

#23: Two weeks after being charged with having a stolen rifle in a hijacked car, he allegedly shot a man with a rifle after getting out of a hijacked car (June 11, 2022)

#24: Gunman left a woman paralyzed in River North just 4 weeks after officials sent his felony gun case to a “peace circle,” prosecutors say (June 13, 2022)

#25: Teen acted as murderer’s driver while awaiting trial for carjacking, stolen car cases: prosecutors say (July 6, 2022)

#26: Man shot victim 5 times, days after being charged in a felony narcotics case, prosecutors say (July 7, 2022)

#27: Concealed carry holder shot man who opened fire on his car at McDonald’s, prosecutors say (July 14, 2022)

#28: Terrorism, attempted murder charges filed against man who allegedly detonated bomb on Pink Line in May (August 8, 2022)

#29: Three-time felon shot robbery victim while on bail for felony gun case, prosecutors say (August 23, 2022)

#30: Concealed carry holder shoots 7-time felon who tried to kill him, prosecutors say. That man was on bail for a felony gun case. (August 25, 2022)

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