Pilsen man admits he set fire to a CPD vehicle while wearing Joker mask during 2020 riots

A magistrate judge found that video of the incident “is indeed quite damning,” and wrote that Timothy O’Donnell also “self-reported that he has gone by the name ‘The Riddler’ in the past.”

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A man alleged to be Timothy O’Donnell poses in front of a burning Chicago police car in Chicago.

A man alleged to be Timothy O’Donnell poses in front of a burning Chicago police car in Chicago.

U.S. District Court records

A Pilsen man admitted Thursday that he set fire to a Chicago police vehicle downtown while wearing a Joker mask during the widespread rioting and looting in the city in May 2020.

The case against Timothy O’Donnell, 32, became among the most high-profile to result from the rioting and looting here in the wake of George Floyd’s murder by then-Minneapolis Police Officer Derek Chauvin. Its notoriety is due in large part to the jarring images —captured by the Sun-Times and others —of a man in a clown mask amid the chaos that day.

O’Donnell previously denied he set fire to the police vehicle in the 200 block of North State Street on May 30, 2020. During a police interview, O’Donnell told authorities, “I do not stand for the exploitation of me and using me as a puppet to create an image,” according to court records.

But he pleaded guilty Thursday to obstructing law enforcement amid a civil disorder and admitted he used a lighter to ignite a piece of cloth that he put in the vehicle’s gas tank. His plea agreement acknowledges he owes $58,125 in restitution to the Chicago Police Department. A prosecutor said O’Donnell faces a likely prison sentence of around three or four years.His sentencing is set for June 14.

After O’Donnell’s arrest, U.S. Magistrate Judge Gabriel Fuentes found that video of the incident “is indeed quite damning,” in part prompting him to rule that O’Donnell should be held in custody while awaiting trial. Fuentes noted that, in addition to wearing a “Joker” mask, O’Donnell “self-reported that he has gone by the name ‘The Riddler’ in the past.”

A man in a clown mask walks past a burning Chicago Police Department SUV near State and Lake on May 30, 2020.

A man in a clown mask walks past a burning Chicago Police Department SUV near State and Lake in the Loop on May 30, 2020, as thousands of protesters in Chicago joined national outrage over the killing of George Floyd in Minneapolis police custody.

Ashlee Rezin/Sun-Times file

However, O’Donnell’s lawyers scored a partial victory last summer. U.S. District Judge Andrea Wood found that O’Donnell had invoked his right to counsel when authorities tried to get him to identify himself as the person wearing the mask during the riots. At one point, O’Donnell said, “I’m in fear. I’m not going to say anything further on that matter without a lawyer present.”

Woods’ ruling suppressed any statements O’Donnell made about whether he wore the mask after he made that comment.

Federal prosecutors charged O’Donnell on June 2, 2020, after investigators tied him to the incident through a “PRETTY” tattoo seen on the neck of the person wearing the mask. Video provided by a witness showed O’Donnell wearing the mask, holding a lit object and placing it in the gas tank of the CPD vehicle. Authorities said the vehicle burst into flames.

A photograph taken by a witness also showed O’Donnell handling the gas tank, according to the feds. In another, O’Donnell appeared to be sitting on the ground, wearing the Joker mask while the vehicle burned.

A third photograph apparently showed O’Donnell posing in the Joker mask in front of the burning car. In that one, a tattoo that says “PRETTY” can be seen on the neck of the person wearing the mask. A CPD photo of O’Donnell revealed the same tattoo.

Chicago police photo of Timothy O’Donnell

Timothy O’Donnell

U.S. District Court records

A family member told law enforcement that O’Donnell lived in a room in an apartment in the 700 block of 19th Place. Authorities obtained a search warrant and searched the apartment. The feds say they found a Joker mask in a bedroom.

When it comes time for O’Donnell to be sentenced, his lawyers will likely point to the separate case of Jacob Fagundo, a School of the Art Institute student who also set fire to a Chicago police vehicle during the May 2020 riots downtown. U.S. District Judge Robert Gettleman gave Fagundo three years of probation, compared to the year-and-a-half O’Donnell has already spent behind bars.

Fagundo surrendered to Chicago police when he realized he was wanted by authorities, and a prosecutor described him as “genuinely remorseful.” Gettleman agreed at sentencing that the crime appeared to be an aberration in Fagundo’s behavior.

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