Chicago’s former head city attorney slammed Democratic Mayor Lori Lightfoot’s "disaster" tenure in a new op-ed after City Council voted on Wednesday to pay $2.9 million to a woman who was handcuffed by police officers while she was naked during a botched 2019 raid on her home. 

The unanimous vote to pay Anjanette Young $2.9 million was widely expected, coming two days after a council committee voted to recommend that the full council accept the settlement and after the city’s law department said Young’s attorney had agreed to the amount.

Lightfoot used the settlement at the taxpayer's expense to "jump-start her reelection campaign," Mark Flessner, who resigned after the Law Department attempted to withhold video of the raid on the wrong address, wrote in a recent op-ed for the Chicago Tribune. 

CHICAGO POLICE SERGEANT UNDER INVESTIGATION FOR ALLEGEDLY SUPPORTING A PROPOSED CONSERVATIVE GROUP 

Flessner outlined how officers executed a search warrant at the wrong address and Young was forced to stand for six seconds uncovered and then another 10 minutes handcuffed and covered with a blanket while officers secured the home. Recognizing the embarrassment Young must have felt and that she should have been compensated, Flessner said the settlement should have been far less, around $50,000. 

Chicago's Mayor Lori Lightfoot

Chicago's Mayor Lori Lightfoot speaks during a science initiative event at the University of Chicago in Chicago, Illinois, U.S. July 23, 2020. REUTERS/Kamil Krzaczynski (REUTERS/Kamil Krzaczynski)

The $2.9 million settlement was substantially more than the kind of money men who served years in prison after being wrongfully convicted had ever received, Flessner said. 

Lightfoot "has made a deal with the national civil rights movement to raise money for her reelection," he wrote. "In exchange for national civil rights leaders donating millions of dollars to her campaign, she will do their bidding, like she did in the Young case. Chicago will be poorer for it." 

"The mayor publicly criticizes those who work for her and provides little to no guidance. She belittles the City Council, the police and fire departments, and the teachers," Flessner added. "She has no professional respect for any of the hardworking, dedicated public servants who make this city run day to day. That is why her tenure has been a disaster." 

Lightfoot responded to the criticism during an unrelated press conference Wednesday, explaining that she asked for Flessner’s resignation because she "utterly lost confidence in his ability to function as the corporation counsel" and acted without consulting her first to work to stop a media outlet from publishing the footage of the controversial raid. "Fundamentally, what was clear, is he just didn’t see [Young]," Lightfoot said. "He didn’t value her experience in that moment, as we all saw in that video."

Before the vote Wednesday, Chicago Alderman Maria Hadden said the council's decision to pay the money was the correct way of "admitting we were wrong and that the city did something wrong."

Anjanette Young and attorney Keenan Saulter speak regarding developments on Young's case and efforts to work with the City of Chicago to bring the matter to a resolution outside of the Thompson Center in Chicago on June 16, 2021. Young was the victim of a botched raid by Chicago police two years ago when police entered the wrong home. 

Anjanette Young and attorney Keenan Saulter speak regarding developments on Young's case and efforts to work with the City of Chicago to bring the matter to a resolution outside of the Thompson Center in Chicago on June 16, 2021. Young was the victim of a botched raid by Chicago police two years ago when police entered the wrong home. 

"We need to fix the system and fix the policies so we don’t keep making the same mistakes," she said.

With the settlement, the city avoided what Chicago Corporation Counsel Celia Meza said could have been a much larger price tag had Young’s lawsuit gone to trial. 

And the city’s case had serious problems, starting with the fact that the officers — as Young told them repeatedly — were at the wrong address. More recently, the Civilian Office of Police Accountability recommended the suspension or firing of eight officers involved in the February 2019 raid.

Young, a social worker, was getting ready for bed when several officers serving a search warrant stormed into her apartment, and handcuffed her while she was naked. 

The city’s law department said Young was naked for 16 seconds but the covering they put on her kept falling off before she was allowed to get dressed several minutes later.

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"No amount of money could erase what Ms. Young has suffered. No amount of money could provide Ms. Young with what she truly wants — which is to never have been placed in this situation in the first place," Young’s attorney said in a statement Wednesday. 

The Associated Press contributed to this report.