As Cook County voters begin to decide who will oversee billions in public spending and the county’s property tax system, a review of tax returns from leading Democratic candidates shows sharply different sources of wealth, investment strategies and levels of financial disclosure.
Two-term incumbent Assessor Fritz Kaegi reported seven-figure investment gains, and he paid nearly $780,000 in combined state and federal taxes over four years. His challenger, Lyons Township Assessor Patrick Hynes, disclosed income from several suburban properties he owns.
Four-term County Board President Toni Preckwinkle relied on her public salary, pension and Social Security income, while her challenger, Brendan Reilly, made do with his Chicago aldermanic salary and a recent reentry into media production work.
The Chicago Tribune requested the past four years of tax returns from the Democratic candidates for Cook County Board president and assessor and compared them with mandatory statements of economic interest filed with the Cook County clerk and the Chicago Board of Ethics. The exercise, voluntary but common in major elections, offers a window into candidates’ financial lives — including potential conflicts of interest — and into how much information each is willing to share with voters.
The candidates varied slightly in what they provided. Preckwinkle released both federal and state returns with full itemized deductions. Kaegi supplied four years of federal and state returns but withheld details about his deductions. Reilly released only the top pages of some federal returns and did not share state filings. Hynes supplied state and federal returns, but only after assurances that Kaegi’s camp did the same.
Kaegi: Investments paying off
Unsurprisingly, Kaegi, a former mutual fund portfolio manager, reported the highest income of the group.
Before his 2018 election as assessor, Kaegi spent more than two decades in finance, including 13 years at Columbia Wanger Asset Management. His personal wealth has allowed him to self-fund his campaigns and refuse contributions from property tax attorneys, though the scale of his investment income has not previously been disclosed in detail.
Kaegi’s public salary ranged from $125,000 in 2021 and 2022 to $137,500 in 2023 and $141,625 in 2024. But joint federal filings with his wife, Rebecca, a Russian teacher in the Noble Network of charter schools, show adjusted gross income fluctuating between about $350,000 and $1.3 million over the four years.
Most of that income came not from wages, but from investments. Kaegi reported between $77,000 and $90,000 in annual dividends, along with capital gains of $680,000 in 2021, $590,000 in 2022, $109,000 in 2023 and more than $1 million in 2024.
Required county disclosures show Kaegi owned and sold stock or securities in major corporations, including 3M, Boeing, PepsiCo, General Electric, Visa, Bank of America and Procter & Gamble, as well as tech giants Meta and Alphabet. He also owned stock in Berkshire Hathaway, run by Warren Buffett. Exact values are not required to be disclosed in the county ethics statements, but Kaegi earned enough from investments in three of the four years to trigger the 3.8% net investment income tax.
How and when Kaegi invests will affect his overall yield if and when he cashes out, but so far, market data indicate he’s chosen wisely. GE stock is up nearly 500% over the past five years. Berkshire Hathaway is up 113%, Google is up 260% and Meta is up 138% over the same span.
Kaegi paid just under $780,000 in combined state and federal taxes from 2021 through 2024. His effective federal tax rate — total taxes divided by total adjusted gross income — ranged from 13% to nearly 20%.
Hynes: Took losses on rental properties
Hynes, the Cook County Democratic Party’s endorsed challenger to Kaegi, reported far lower total income overall, ranging from about $97,500 to $304,000. He filed jointly with his wife, Margaret, a former teacher at St. John of the Cross in Western Springs and a current accountant at the nonprofit Helping Hand.
Hynes’ adjusted gross income dipped as low as $89,000 in 2022 and peaked at $303,000 in 2023, when he reported a capital gain of about $200,000 tied to the sale of a home in LaGrange Highlands.
His campaign said in a statement that Hynes and his family sold the property “in order to help cover the cost of college for one of his children.”
The sale was one of several real estate holdings disclosed on his county economic interest statements. Over the years, Hynes reported owning multiple rental properties — including homes, condos and a small apartment building — in Summit, Countryside, LaGrange Highlands and Crestwood.
Hynes’ father, Tim, “also purchased and renovated rental properties when Pat was a kid and taught him how to do a lot of the work on his own. He’s been renovating and fixing residential properties since he was a teenager,“ Becky Carroll, a campaign spokesperson, said in an email.
One of those other properties “will also eventually be sold to help cover the cost of college for one of his other children,” she said.
Hynes’ returns show he took losses on all of his rental properties between 2021 and 2024. While he made somewhere between about $63,000 and $88,000 in rental income, that was offset by expenses, depreciation and the cost of mortgage interest. Those losses reduced Hynes’ “additional income” line.
In addition to serving as Lyons Township assessor, a position that paid $58,707 in 2024, Hynes has worked as a temporary assessor in Lemont Township, which his campaign said earned him $1,000 per month. He also serves as an unpaid volunteer firefighter in Western Springs and previously worked in the Cook County assessor’s office, including briefly under Kaegi. His township assessor job was a pay cut compared with his county salary.
Hynes took the standard deduction each year and paid about $61,000 in federal taxes over four years. His effective federal tax rate ranged from 3.7% to 13.3%.
Preckwinkle: Pension supplementing salary
Preckwinkle, the longest-serving official in the field, reported income between $160,700 and about $285,000 over the four years reviewed.
Her public salary rose from $170,000 in 2021 and 2022 to $192,610 in 2024. But a significant portion of her income came from retirement benefits. At 78, Preckwinkle receives both a city pension from her years as a 4th Ward alderman and Social Security.
In 2023, she received a nearly $126,000 distribution from her city pension, according to her campaign. Her annual pension payment in 2024 was $84,759, while Social Security benefits increased from $13,000 in 2021 to $15,516 in 2024.
Unlike Kaegi, Preckwinkle reported little investment income. Her only notable capital gain was about $24,000 in 2021, the year she sold a condominium in the 5000 block of South Woodlawn Avenue. She also owns a cabin in her home state of Minnesota and recently purchased a new $1 million home in Kenwood.
Preckwinkle itemized deductions for charitable giving — between roughly $8,000 and $13,500 annually — and mortgage interest. Her effective federal tax rate ranged from 14.4% to 20.5%.
Reilly: Uptick due to TV projects
Reilly, an alderman for much of Chicago’s downtown area who is challenging Preckwinkle, released partial federal returns showing total joint income with his wife, Kristin, ranging from about $155,000 in 2022 to $334,000 in 2024. He did not provide 2021 or any state returns, citing difficulty reaching his accountant.
Reilly’s aldermanic salary rose modestly from $117,600 in 2022 to $125,208 in 2025 — Reilly has at times turned down inflation-adjusted raises. The spike in 2024 income came from renewed consulting and media production work. Reilly said he earned $40,000 producing television projects that year, while his wife returned to her career in media buying.
Reilly disclosed outside work for Relentless Campaigns and an ownership stake in Uncle Dougie’s Sauce Co. in city ethics filings. The sale of the sauce company in 2022 generated a $15,000 capital gain and offsetting loss, he said.
After taking the standard deduction and $38,000 in qualified business income, the couple reduced their 2024 taxable income to about $251,000. They reported minimal investment dividends and took no property tax deductions, renting a River North loft.
Reilly’s effective federal tax rate climbed from just under 12% in 2022 to 24% in 2024.
