The city of Chicago’s former top lawyer under Mayor Lori Lightfoot ripped her tenure as a “disaster” in an opinion piece and criticized the city’s $2.9 million settlement of the Anjanette Young lawsuit.

Mark Flessner, who was forced to resign as corporation counsel after the Law Department fought to withhold video of a botched police raid on Young’s home, wrote that the settlement was excessive and that the lawsuit “would have probably not made it to trial.”

Before aldermen settled Young’s lawsuit Wednesday, the city had succeeded in getting several counts of Young’s lawsuit dismissed, though the case remained alive.

In the opinion piece, Flessner said he recommended a settlement “in the range of $50,000″ before he left the department.

He also criticized Lightfoot and her leadership style, saying her approval rating has “plummeted” for “the same reason much of the senior staff has departed the administration.”

“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 wrote. “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.”

At an unrelated news conference Wednesday, Lightfoot said she asked for Flessner’s resignation because she “utterly lost confidence in his ability to function as the corporation counsel” and criticized his handling of Young’s case.

“There were a number of things leading up to the decision, certainly starting with the fact that he authorized without much consideration the filing of an injunctive action against a media company without any consultation or even giving me notice that it had happened,” Lightfoot said, referring to her administration’s initial efforts to suppress the release of the video. “The fact that, over the course of that week, he repeatedly said disparaging things related to Ms. Young.”

“Fundamentally, what was clear, is he just didn’t see her. He didn’t value her experience in that moment, as we all saw in that video,” Lightfoot added.

Flessner also lost the confidence of senior staff, aldermen and the public, Lightfoot said. She also cited the City Council’s unanimous approval of the $2.9 million settlement as proof that the offer is fair.

“He’ll continue to say whatever he says. God bless him, that’s his right under our Constitution,” Lightfoot said.

The Tribune previously reported that Flessner shrugged off the incident during a staff call with Lightfoot the morning after CBS-2 first aired disturbing footage from the raid last December, according to sources.

After a staffer asked about the case, Flessner said it wasn’t a “big deal” and noted officers let Young get dressed after she was handcuffed without any clothes on, sources said.

Lightfoot kept Flessner on board for days after the remark, but accepted his resignation the following weekend as the scandal snowballed.

Young’s attorney released a statement Wednesday saying in part: “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.”

The statement said Young wanted to shed light on the “horrific” raid so those involved would be held accountable.

Flessner was a longtime friend of Lightfoot’s whom she tapped to lead the Law Department after becoming mayor in 2019. She asked him to resign in December 2020 amid criticism of her administration’s handling of police video in the Young case.

Earlier this year, the Tribune reported that Lightfoot and Flessner were in a heated dispute over whether she agreed later to give him city business.

About three months after Lightfoot requested his resignation, Flessner asked the Chicago Board of Ethics on March 29 for an advisory opinion on whether he could accept city cases, according to an email released in response to an open records request.

Flessner said the Department of Law asked him whether he could take on the work, according to the Board of Ethics’ opinion.

Lightfoot “has no objection,” Flessner added, according to the board.

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After receiving the opinion from the city’s ethics chief, Steve Berlin, at 9:52 a.m. on April 13, Flessner forwarded the opinion to Lightfoot. The mayor then forwarded it to her then-chief of staff, Maurice Classen, and interim corporation counsel Celia Meza seven minutes later, writing only, “FYI.”

In September, however, Lightfoot sent a letter to the Board of Ethics saying she “was recently made aware” of Flessner’s statement that she had no objections to him receiving city work.

“Please be advised that I made no such comment to Mr. Flessner,” Lightfoot wrote in the letter, dated Sept. 17. “I have never indicated to him that I would approve of his engagement as outside counsel to the city on any matter.”

Five days later, Lightfoot’s administration released the April emails to the Tribune in response to a public records request. The mayor’s office previously declined to comment when asked why she didn’t deny Flessner’s claim in April, when she first received the ethics opinion.

He has not done any work for the city since his resignation.