A 23-year-old man pleaded guilty in federal court Tuesday to charges of inciting and participating in a riot that left 13 officers injured after encouraging others to join in the looting in downtown Chicago during the summer of 2020.
James Massey was charged in May 2021 with one count of using a facility of interstate commerce to incite a riot. He faces a maximum prison sentence of five years in prison and will be sentenced during his next court date scheduled for May 10, according to the Department of Justice (DOJ).
The DOJ said Massey used his Facebook account to help set off the rioting and looting in Chicago. On August 9, 2020, he posted multiple videos and messages on Facebook calling for people to go to downtown Chicago and engage in looting and property damage.
According to the criminal complaint, Massey sent several messages to people on Facebook telling them to meet up at a certain location before traveling to the downtown area. Massey told others that the looting starts at 12 a.m. and urged them to “BRING YA TOOLS SKI MASKS AND GLOVES.”
Massey posted videos on Facebook live throughout the night. Around 11:45 p.m. on August 9 he posted a 10-minute video saying, “I ain’t missing out. I am ready to steal,” per the complaint.
During the riots, hundreds of people were in downtown Chicago looting, damaging retail stores and fighting with police. At least two people were shot and 13 police officers were injured. Law enforcement recovered roughly five firearms and over 25 people were arrested in connection to the riots, the complaint stated.

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One of the locations Massey mentioned was a marijuana dispensary. Footage at the dispensary showed roughly 12 people arriving in three vehicles. Several individuals broke into the building by smashing windows with tools taken from Massey’s vehicle. Shortly after, people could be seen stealing boxes out of the business and the complaint stated it’s believed Massey was acting as a lookout while others looted.
Massey then moved on to hit several other stores throughout the night. Surveillance video from one establishment showed Massey walking up to the building with a tire iron in his hand while another person broke the store’s window. Massey and several others entered and alleged they grabbed some coats before moving on to loot and vandalize a convenience and a cellphone store.
Update 02/16/22, 1:40 p.m. ET: This article has been updated with details from the criminal complaint against James Massey.
Update 02/16/22, 1:00 p.m. ET: This article has been updated with background information from the Department of Justice.