2 men head to prison for firing on a car in Rogers Park — one was on electronic monitoring, the other was on his last day of parole

Two men who allegedly opened fire on a car in Rogers Park—one was on electronic monitoring, the other was wrapping up parole—have pleaded guilty in exchange for fairly lengthy prison sentences.

Sherwin Flowers, 33, was enjoying his last day of parole for drug and gun cases when police arrested him in November 2020. Deshawn Gillette, 26, was on electronic monitoring for two felony drug cases he picked up while he was on parole for robbery.

Sherwin Flowers in 2017 | CPD

Late on November 3, 2020, a gunman rolled up in a car and opened fire on a group of people who were standing on a street corner in the 7600 block of North Bosworth. The group scattered and dove for cover. Chicago police officers who were keeping an eye on the targeted group via a nearby POD camera saw it all happen.

About 15 seconds later, as the cops continued watching the video feed, Gillette returned to the corner, pulled a handgun from his waistband, and fired a shot down the street toward the gunman’s vehicle, Assistant State’s Attorney Jocelyn Schieve said during his bail hearing.

According to Schieve, there were several innocent bystanders downrange from where Gillette fired the gun, but none was injured. She said officers in the camera room immediately recognized Gillette, whose face was not covered, from previous encounters.

The camera also recorded video of Flowers firing three shots at the car before he ran away, prosecutors said. Cops immediately recognized him, too.

At the time of the incident, Gillette was supposed to be in his house on electronic monitoring for two separate narcotics delivery cases that he picked up while he was on parole for armed robbery last year, Schieve said.

“He was under a seven-year armed robbery sentence, not supposed to be in possession of even a bullet. On house arrest for two cases,” Judge John Lyke said during Gillette’s hearing.

Deshawn Gillette | CPD

“Had he adhered to house arrest, maybe he wouldn’t have, number one, got shot at and, number two, returned fire shortly thereafter,” Lyke continued.

Both men have now pleaded guilty in connection with the November 2020 allegations.

Gillette received ten years for aggravated unlawful use of a weapon with a previous gun conviction and one year for possession of a controlled substance. He is scheduled to be paroled in January 2025.

Flowers, who has three prior gun convictions, including a 2006 case in which he shot someone, pleaded guilty to aggravated discharge of a firearm into an occupied vehicle. He received seven years and is expected to be released in May 2024.

Judge Michael Hood oversaw the cases and handed down the sentences.

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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. Our editorial email address is news@cwbchicago.com