The top attorney for the city of Chicago has for several years received homestead tax exemptions by claiming both a west suburban home and a condominium on the Near South Side as his primary residence in an apparent violation of a state law that prevents homeowners from earning those tax breaks on multiple properties.

Mayor Lori Lightfoot initially told reporters Monday she believed City Corporation Counsel Mark Flessner never received multiple homestead exemptions. Government records, in fact, show he received thousands of dollars in tax breaks in 2016, 2017 and 2018 for both a single-family house in Naperville and the Chicago condo.

Later on Monday, the mayor’s office reversed course, acknowledging Flessner had “mistakenly claimed a homestead exemption for both his Chicago and Naperville properties.”

“Now that this mistake has been brought to his attention, he will be paying back . . . the amount he received from the additional exemption,” said Anel Ruiz, a spokeswoman for the mayor, adding that Flessner owes roughly $2,500 dating back to 2015.

Ruiz said Flessner’s primary home has been in Chicago since he was hired as the city’s top attorney. She noted he has not filed to claim a homestead on any property in 2019.

The tax breaks both fall under the state’s general homestead exemption, which applies to “residential property that is occupied by its owner or owners as his or their principal dwelling place,” according to state law. Individuals who run afoul of that provision by receiving exemptions on more than one home could be ordered to repay unpaid taxes, as well as interest and penalties.

The dual homestead exemptions held by Flessner, hired as the Lightfoot administration’s top lawyer in May, came to light after the firing last week of city law department spokesman Bill McCaffrey.

Mayor’s about-face

During a Monday morning news conference that was part of an event to roll out new Sunday hours at some city libraries, Lightfoot defended her decision to fire McCaffrey, who previously worked for mayors Rahm Emanuel and Richard M. Daley in a variety of communications positions.

Her statements followed a source in her office telling the Politico Illinois Playbook that McCaffrey had spread “disinformation about a residency issue related to” Flessner.

The Sun-Times began investigating Flessner’s homestead exemptions over the weekend. On Sunday, the mayor’s office provided the Sun-Times with photographs of a driver’s license issued to Flessner in late May and a voter registration card issued weeks after Lightfoot was elected in April; both list a Chicago address.

However, state voter registration records still list Flessner’s polling place as a Naperville church.

When a Sun-Times reporter showed up at the Chicago condo Sunday afternoon, Flessner wasn’t home.

Lightfoot was asked during her Monday news conference whether her corporation counsel has a “residency problem.”

“No. That’s totally false. That’s totally false,” she said.

She also was asked about Flessner’s homestead exemptions. “He didn’t have homestead exemptions in two places,” Lightfoot said.

After the news conference, the Sun-Times published its story noting Flessner’s dual homestead exemptions in 2017 and 2018.

About 20 minutes later, the mayor’s office released its statement acknowledging Flessner had mistakenly gotten tax breaks on both the Naperville and Chicago homes.

McCaffrey, who was fired Friday, had raised a series of issues with Flessner before he was terminated, a source close to the ex-spokesman said.

During her news conference, Lightfoot said she fired McCaffrey “for cause” after receiving information last week that raised “serious questions” about his “professionalism and his judgment.”

“I’ve set a pretty clear standard [for] anyone who’s gonna work in our administration. They have to do their job at a high degree of competence. They have to be a good colleague. And . . . they have to have the highest ethical standards, which means they can’t lie — either through omission or commission,” the mayor said.

“Serious issues regarding professionalism and judgment were raised and, on the basis of that, there was plenty of information to fire him for cause, which is what happened. Period.”

Reached by phone, McCaffrey declined to comment.

‘McCaffrey was your buddy’

A visibly angry Lightfoot also scolded the news media for taking information from “anonymous” single sources and running with it in defense of McCaffrey, whom she called “your buddy.”

“I’ve seen the Twitter play of some of you over the course of the weekend. And I have to say I’m disappointed that — on the basis of a single source, unnamed — that you all are putting this out as if it’s” true, Lightfoot said.

“Obviously, Bill McCaffrey was your buddy. But I hope that we are not getting to a new standard in media here in Chicago where we have a bunch of unnamed sources. There’s no other information provided. They’re throwing out a bunch of chum on the water. And people are biting at it as if it’s the truth. Because the things that have been put out that I’ve seen are demonstrably false and could easily be proven so with a little bit of diligence, which I would assume reporters who are serious about this would do.”

Flessner worked nearly 13 years as a prosecutor in the U.S. Attorney’s Office for the Northern District of Illinois, including during four years Lightfoot worked there. Flessner is the former treasurer of Lightfoot for Chicago, the mayor’s primary campaign fund and the one she used to bankroll her mayoral campaign.

Prior to being named Chicago’s chief legal officer, Flessner practiced at Holland & Knight, an international law firm, where he represented clients facing government scrutiny for criminal, civil and regulatory matters.

Records show Flessner receives an annual city salary of $178,872.

Latest residency controversy

The city’s residency requirement has been a hot button topic since Lightfoot took office in May.

In recent months, a top aviation official and a mayoral adviser have both been ousted from their posts after residency issues were brought to light.

Kieran Sheridan, chief operating officer of the Chicago Department of Aviation, resigned in September after an NBC 5 investigation revealed he resided with his family at a Naperville home while claiming he lived at an apartment on the Northwest Side.

Just last week, the Chicago Tribune reported that Lisa Schneider-Fabes was resigning from her volunteer position as an advisor to Lightfoot and her paid job at World Business Chicago, a public-private nonprofit that aims to bolster economic development in the city. Schneider-Fabes, who lives in north suburban Wilmette and serves on the local school board, stepped down as Inspector General Joe Ferguson looked into the arrangement, the Tribune reported.

Contributing: Jake Wittich