Chicago's top lawyer got same residency tax break on two homes - one in Chicago, the other in Naperville - for years

The top attorney for the city of Chicago has for several years received homestead tax exemptions by claiming both a Naperville 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. However, government records show he received tax breaks in 2016, 2017 and 2018 for both homes.

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.

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