Man sentenced to 15 months in federal prison for inciting riot in downtown Chicago during 2020 unrest

A Chicago man was sentenced to 15 months in federal prison Tuesday for inciting and participating in looting during the civil unrest that gripped the city in August 2020, including a break-in at a marijuana dispensary.

James Massey, 23, pleaded guilty earlier this year to incitement of a riot, admitting in a plea agreement with prosecutors that he posted multiple videos and messages on Facebook calling for people to travel to downtown Chicago to engage in property damage and looting.

Massey was later captured on surveillance video helping to loot and destroy four businesses, including a West Loop cellphone store and the Windy City Cannabis marijuana dispensary on the Near North Side.

The sentence was among the more significant penalties handed down in Chicago’s federal court so far stemming from the civil unrest that broke out in cities across the country in the summer of 2020 following a series of high-profile police incidents, beginning with the murder of George Floyd in Minneapolis in late May.

In rejecting a request by the defense for probation, U.S. District Judge Matthew Kennelly said Tuesday that Massey did a disservice to the legitimate protesters who were trying to call attention to the issue of police misconduct.

Kennelly also acknowledged an attempt by Massey’s attorney to draw parallels to the Jan. 6 riot at the U.S. Capitol, saying both cases involved “a bunch of people who basically said to themselves, ‘We don’t like what’s happening out there so we’re going to destroy a bunch of things.’ ”

“If that’s the way we’re going to react, the law’s gone,” Kennelly said during the videoconference hearing. “It’s mob rule, it’s vigilante justice and nobody wants that.”

Massey has been in custody at the Metropolitan Correctional Center since August 2021 when he was arrested while trying to illegally purchase a handgun at an Indiana gun store while free on bond. With good behavior, he would eligible for release in about five months.

Before Kennelly handed down the sentence, Massey issued a short apology to the court, saying the kind of behavior he engaged in that night was behind him. He also said he was “not the only one” who posted similar things on social media, and that he believes he was targeted by law enforcement “because I had the most views.”

According to court records, Massey’s call to action began with messages he posted to Facebook on Aug. 9, 2020, telling people to meet him at 63rd Street and South Racine Avenue so they could then travel downtown as a group. Shortly before midnight, Massey posted a photo of himself on Facebook with the caption, “Lets get ready to steal (expletive),” the complaint alleged.

“ATTENTION ATTENTION LOTTING START AT 12am,” another post stated, according to a screen grab included in the charges. “DOWNTOWN AREA AND UP NORTH AREA ONLY BRING YA TOOLS SKI MASK AND GLOVES.”

Several people responded to the messages to discuss their plans to loot and comment on how it was going, including one Facebook user who stated to others in the group, “We like 13 cars deep,” prosecutors said.

Early on Aug. 10, several people smashed the windows of the marijuana dispensary in the 900 block of West Weed Street, using tools they had taken from the trunk of Massey’s vehicle, which was parked in the dispensary’s parking lot, the complaint said.

About a half-hour later, Massey was captured on surveillance video walking up to a retail store in the 800 block of North Michigan Avenue brandishing a tire iron, while another person broke the store window, the complaint stated.

Massey and several others allegedly entered the store and stole numerous coats before returning to Massey’s vehicle, the complaint stated. Minutes later, a person posted to the Facebook group that they had “just hit” the store, according to the charges.

Massey also participated in the looting of a convenience store in the South Loop neighborhood and the Verizon store in the West Loop, the complaint stated.

When Massey was warned that his posts inciting the looting were being circulated on social media, he allegedly replied he didn’t care, according to criminal charges. “(Expletive) dem...freedom of speech,” he allegedly wrote.

In asking for a sentence of up to 21 months, Assistant U.S. Attorney Aaron Bond said the damage to just two of the looted stores was estimated at $185,000. He also said that Massey’s actions that night were akin to “taking a match to a kerosene-soaked wood.”

Massey’s attorney, Ilia Usharovich, said that while what happened was “terrible,” it was a spur-of-the-moment crime and that keeping Massey behind bars would do nothing to heal the underlying causes for the looting.

“He’s a young kid who made foolish, foolish decisions,” Usharovich said. “He wanted to be recognized. He wanted to be part of something.”

But Kennelly said regardless of how much it was thought through, Massey still committed a “really serious crime.”

“If stupidity were a defense to a crime, there wouldn’t be any crimes anymore,” the judge said.

jmeisner@chicagotribune.com