“High ranking” gang member strikes plea deal in Rogers Park shooting

Max Chessher | CPD

An alleged high-ranking gang member who police said shot a man near the Loyola Red Line station two summers ago has been sentenced to just 7 years in prison after striking a plea deal with prosecutors. After receiving credits for good behavior and time served before pleading, he’s scheduled to be paroled in 16 months.

On July 27, 2018, someone fired shots from a black sedan in the 6500 block of North Winthrop, striking a 17-year-old male in the leg. The victim flagged down a passing car, and the driver took him to Presence St. Francis Hospital for treatment.

Police said Max “Maxo” Chessher, 30, was identified on surveillance video at the shooting scene as well as at the Loyola Red Line station where he allegedly dumped a handgun into a garbage can after the crime. He was arrested about a month after the shooting. Chessher was on parole at the time for two concurrent 6-year sentences he received for methamphetamines.

A grand jury returned a true bill that charged Chessher with six counts of attempted murder, two counts of aggravated battery with a firearm, and other felonies in connection with the shooting.

But Chessher, who police said in court records is a “high ranking member” of the Insane Cutthroat Gangsters also known as Pooh Bear Gang, reached a deal with prosecutors. Under the agreement, he pleaded guilty to one count of unlawful use of a weapon. In exchange, he received a 7-year sentence, and the state dropped all other charges.

Chesser was given credit for 763 days that he spent in jail after being arrested. He will also receive the state’s standard 50% sentence reduction for good behavior in custody. His early release date is now set for February 18, 2022.

Judge Mary Brosnahan oversaw the shooting case. 

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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