Guilty pleas, sentencings begin in feds’ summer rioting cases, but investigations still ongoing

Not every case is necessarily on track for a guilty plea. And unsealed court records show how feds have tried to identify still at-large suspects through cellphone data.

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A Chicago Police Department SUV is set on fire near State and Lake in the Loop as thousands of protesters in Chicago joined national outrage over the killing of George Floyd in Minneapolis police custody, Saturday afternoon, May 30, 2020. | Ashlee Rezin Garcia/Sun-Times

Ashlee Rezin Garcia/Sun-Times, Ashlee Rezin Garcia/Sun-Times

Ten months after historic unrest and looting swept across Chicago’s downtown and into its neighborhoods, a judge on Wednesday handed down what appears to be the first federal prison sentence to stem from what a defense attorney called “difficult times” in the city.

Though D Angelo D. Chester, 32, was not accused of participating in the violence or property damage that began May 30, he is among a handful of defendants whose cases feature some connection to the unrest and are now working their way through the federal court system. 

Federal authorities say investigations into the rioting continue. This month prosecutors leveled a rarely filed charge against James Massey, of Chicago, accusing him of using a facility of interstate commerce to incite a riot during the unrest in August. They also last month charged three people with setting fire to a CTA van on May 30


A Chicago man has been arrested and charged in federal court with inciting a riot last August in Chicago.

U.S. Attorney’s Office

Meanwhile, a recently unsealed search warrant affidavit obtained by the Chicago Sun-Times shows how federal authorities tried to identify two people involved in setting fire to a cosmetics store on the South Side through cellphone data.

Prosecutors accused Chester of running from Chicago police officers who spotted him at 78th Street and South Kingston Avenue at 9:24 p.m. on June 3 — 24 minutes after the 9 p.m. curfew Mayor Lori Lightfoot set as a result of the rioting. During the chase, the officers said they saw Chester reach into his waistband and throw away what turned out to be a 9mm semi-automatic pistol. 

Chester’s criminal history includes state-court convictions for gun crimes in 2015 and 2017, court records show. Federal prosecutors also said that, six weeks before Chester’s latest arrest, he had been given three years of probation in an aggravated sexual abuse case that involved a “brutal sexual crime against an 8-year-old child.” 

Chester pleaded guilty in December to being a felon in possession of a firearm. And in an in-person hearing Wednesday, U.S. District Judge John Blakey gave Chester more than three years in prison, finding that the risk of Chester committing another crime is significant. 

Defense attorney Ralph Schindler Jr. briefly mentioned last summer’s unrest when he noted that Chester’s crime occurred “shortly after the Chicago riots” and amid the “difficult times in Chicago back then.”

A handful of guilty pleas are also set to occur in the coming weeks in other riot-related cases. Brandon Pegues, who is accused of fleeing police only to fall and drop a gun he was not allowed to have May 31 in the 800 block of South Financial Place, is set to plead guilty Thursday. Gustavo Luna-Barrios, accused of trying to flee police after leaving a looted auto parts store only to be caught illegally with a gun June 1, is set to plead guilty Tuesday.

In one of the more high-profile cases related to the Chicago rioting, Matthew Rupert, of Galesburg, also has a change-of-plea hearing set in federal court in Minnesota for April 7. Rupert allegedly traveled to Minneapolis, and then to Chicago, to loot and riot. He was arrested here May 31. 


Matthew Rupert in February 2018.

Knox County Jail

Not every case is necessarily on track for a guilty plea, though. Defense attorney Amanda Penabad on Tuesday filed a motion challenging the case against Adam Walton. Prosecutors said police saw Walton leave a looted Old Navy in Marshfield Plaza and flee early on June 1. When he returned for his vehicle, they said he told officers there was a gun in the car, even though he has multiple previous convictions, records show. An officer wrote in a police report that he saw the gun in the vehicle’s center cup holder. 

Penabad said the officer later clarified that he only saw the gun after he moved a large pile of merchandise out of the way, meaning it was not in plain view. She also said Walton denied that he told officers about the gun, and “without that statement, the officers had no probable cause to believe a weapon was in the vehicle.”

Other suspects are still at large. Among them are two people who authorities say were involved in the arson of an Ulta Beauty cosmetics store in the 4100 block of South Pulaski Road on May 31. In a recently unsealed search warrant affidavit filed last August, an ATF special agent noted that a neighboring Carter’s store had an open wifi router that might have connected to the cellphone of a suspect in the Ulta.

The feds hoped to search data held by Google generated by devices in a geographical area around the Ulta store during 10-minute and 12-minute time periods during which surveillance footage put the suspects in the store.

ATF spokeswoman Kimberly Nerheim said Wednesday the suspects have not been charged and the investigation is ongoing.

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