‘Joker’ goes to prison for 2020 riot allegations — and others are pleading guilty, too

Timothy O’Donnell, whose image was splashed across the internet after he set fire to a Chicago Police Department squad car during the 2020 riots, received a 34-month federal prison sentence this week.

Timothy O’Donnell sits on the Wabash Bridge minutes before he set the Chicago police squad car on fire in the Loop. | U.S. District Court records

More than two years after the uprising, and nearly two years after another wave of looting hit the city in August 2020, many people continue to fight felony charges stemming from alleged wrongdoing. However, those cases are gradually coming to a close. Here are a few we’ve been keeping an eye on.

Timothy O’Donnell

On May 30, 2020, O’Donnell, 34, strolled throughout the city wearing a “Joker” mask, posing for photos and live-streaming as he walked along Wacker Drive.

“Beautiful day for a barbecue,” he allegedly said, minutes before he set fire to the unattended CPD squad car on the 200 block of North State.

“After setting fire to the CPD vehicle, the defendant stuck around to pose for pictures in front of the wreckage he created,” federal prosecutors wrote in a sentencing memorandum.

Police identified O’Donnell through, among other things, a large tattoo that stretches across his throat.

O’Donnell “has a long history of mental health, substance abuse, and addiction issues … [that] has cast a pall over his entire adulthood and is reflected in his criminal history,” prosecutors wrote.

He “has never held a real job in his life,” the memorandum claimed.

O’Donnell this week apologized to his parents, one of whom was a forensics officer for the Illinois State Police, and the peaceful protesters whose movement he marred.

U.S. District Judge Andrea Wood oversaw the case and sentenced O’Donnell.

Tattoo 2

Antwoine Pittman | CPD

O’Donnell is one of many people who ended up facing felony charges after 2020’s mayhem because people recognized their distinctive tattoos.

Another is Antwoine Pittman.

Prosecutors charged him with looting an Ulta Beauty store on the Magnificent Mile in August 2020 after cops identified his collection of facial tattoos from store surveillance footage.

In addition to having the word “active” tattooed above his left eye (with an upside-down “A”), Pittman also has the letter “B” tattooed between his eyes, the word “spike” above his right eye, and a broken heart tattoo on his cheek, prosecutors said.

His tattoos were so memorable, officers who arrested him one month later for a robbery on the CTA remembered him from Ulta surveillance images they were shown weeks earlier. The upside-down “A” was the mark that played a key role in the identification of Pittman, prosecutors said.

Pittman has pleaded guilty to burglary, escape, and robbery. In exchange, he received five years for the Ulta case. It will run consecutive to a four-year sentence for the robbery and concurrent to a two-year sentence for escape, according to court records.

His time will be cut in half for good behavior and he received 376 days credit for time spent in custody before pleading. In the end, he is expected to be released from prison on August 8, 2024.

U-Haul duo

U-Haul trucks were a weapon of choice for looting crews that ran rampant through downtown in 2020. Crews used the vehicles to ram storefronts, then loaded the trucks with stolen goods.

So, when cops saw a U-Haul making an improper lane change in River North on the evening after the area was ravaged by looters on August 10, 2020, they pulled it over.

As officers spoke with the driver, Marcus Strozier, they heard weird noises coming from the truck’s cargo area. When they opened it, they found 18-year-old Brian Duren hiding inside with a handgun, according to a statement CPD issued the next day. Another gun was allegedly found in the truck’s cab.

Duren pleaded guilty to two felony counts of aggravated unlawful use of a weapon and received a one-year sentence on each charge.

Strozier was also charged with aggravated unlawful use of a weapon. He was AWOL when we last checked the status of his 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