15-month sentence for man charged in downtown looting

James Massey was also ordered to pay $180,000 in restitution to Mag Mile-area stores.

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James Massey was sentenced Tuesday to 15 months in federal prison for his role in inciting looting in August 2020 in Chicago’s Magnificent Mile shopping district.

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An Englewood man was sentenced Tuesday to 15 months in federal prison for his role in inciting looting during a night of unrest in August 2020 that left Chicago’s Magnificent Mile shopping district in shambles.

James Massey, who was caught on surveillance video hauling thousands of dollars worth of coats from a Canada Goose shop on North Michigan Avenue and breaking into a cannabis dispensary on Weed Street, a cellphone store on Washington Street and a convenience store on Clark Street, also will have to pay more than $180,000 in restitution to the retailers.

“Anyone involved in destructive behavior in Chicago — such as rioting — should expect to be held accountable,” U.S. Attorney John Lausch said in a statement. “Our office will continue to work with the FBI, CPD, and our other law enforcement partners to prosecute rioters and others engaged in violent crime.”

Massey, who was 21 when he jumped on Facebook to implore his followers to head downtown the night of Aug. 9, 2020, said he had learned from the eight months he’s spent in the federal lockup downtown. Jailed since August 2021 after he attempted to buy a gun in Indiana while on bond, Massey has lost 15 pounds after another inmate broke his jaw and also caught COVID while in the Metropolitan Correctional Center, his lawyers said.

“I am remorseful, and this has been hard time and I realize this is not how I want to spend the rest of my life,” Massey told U.S. District Judge Matthew Kennelly during an hour-long sentencing hearing that was conducted by video.

“I really do apologize,” said Massey, who had no prior convictions before he was charged in the looting in March 2021. “This is not any kind of behavior you have to worry about with me. I wasn’t the only one out there that made (social media) posts, but I had the most followers.”

The sentence was on the low end of federal sentencing guidelines, and less than the two to two-and-half years requested by federal prosecutors. In a plea agreement with prosecutors, Massey admitted to posting videos and messages on his Facebook account, urging others to head downtown and break into stores.

“ATTENTION ATTENTION (LOOTING) START AT 12 am tonight... WE WILL NOT BE (MESSING) UP THE SOUTH SIDE EAST SIDE OR WEST SIDE DOWNTOWN AREA AND UP NORTH AREA ONLY BRING YA TOOLS SKI MASK AND GLOVES #LETSGOOOOO,” Massey typed as a caption for one of the Facebook videos cited by prosecutors. In charging documents, prosecutors said 766 people watched the video.

In more messages to a Facebook group, Massey gave the locations he wanted to target, including locations where surveillance video showed Massey — who apparently ignored his own advice to bring a ski mask — could be seen stealing from stores.

Massey’s lawyers argued that it was unlikely Massey was the sole, or even a significant instigator of the violence and vandalism that broke out the night of Aug. 9, 2020, as hundreds of people descended on downtown that night, apparently in response to false rumors Chicago Police officers had gunned down an unarmed teenager in Englewood.

As windows were smashed and chaos built in the Loop, Mayor Lori Lightfoot ordered the downtown bridges over the Chicago River to be raised to bar the path of vandals. Police reported 13 officers were injured in confrontations and two civilians were shot.

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