Scandalous, Unethical, Improper, Wrong and Inappropriate

City’s top lawyer got same residency tax break on two homes — one in Chicago, the other in Naperville — for years and years

Mark Flessner has a Naperville house and a Chicago condo. Records show he got a tax break on both for several years as if each was his primary residence, in a possible violation of state law. The city says it is a mistake he’s rectifying.
By Tom Schuba and Fran Spielman Dec 16, 2019, 1:58pm CST


Mayor Lori Lightfoot leaves City Hall with Corporation Counsel Mark Flessner in October. Ashlee Rezin Garcia/Sun-Times file photo


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 a possible 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 that 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 earlier this year. She noted that he has not filed to claim a homestead on any property in 2019.

Those 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 residency of 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.


On Monday, Lightfoot defended her decision to fire McCaffrey after her office accused the longtime City Hall spokesman of spreading disinformation.





The mayor’s office said Flessner is “in compliance with the city residency requirements.” On Sunday, an aide to the mayor 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 that 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 condo Sunday afternoon, he was told Flessner wasn’t home.

On Monday morning, Lightfoot was asked whether her corporation counsel has a “residency problem.”

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

Why then, did Flessner have homestead exemptions in two places?

“He didn’t have homestead exemptions in two places,” Lightfoot said early Monday.

When reporters challenged the mayor’s assertion, the mayor said, “I don’t believe that’s correct.”Mayor Lori Lightfoot on Monday initially said she did not believe Corporation Counsel Mark Flessner has homestead exemptions in two places — one in Chicago, the other in Naperville. The mayor’s office later acknowledged he did. Fran Spielman/Sun-Times



McCaffrey, who was fired Friday, had raised a series of issues with Flessner before he was terminated, a source said. It’s unclear whether Flessner’s residency was among those concerns.

On Monday, 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.”

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 at an unrelated event to roll out Sunday library hours.

“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 four years Lightfoot worked there. Flessner is the former treasurer of Lightfoot for Chicago, her 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.

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.

And just last week, the Chicago Tribune reported that Lisa Schneider-Fabes was resigningfrom 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.