High-profile Chicago real estate industry figures are pouring donations into the Cook County Board President’s race, but are showing less of a united front than they are in the Tax Assessor’s race, campaign finance data shows.
Chicago Alderman Brendan Reilly, who represents much of the Loop and River North, is challenging longtime incumbent Toni Preckwinkle in the Democratic primary for Cook County Board President, which is set for March 17.
As final donations roll in, industry leaders including Fifield Companies’ Steve Fifield, Riverside Investment’s John O’Donnell, Hubbard Street Group’s John McLinden, developer Scott Greenberg, Waterton CEO David Schwartz, Equity Commonwealth REIT CEO David Helfand and members of billionaire Neil Bluhm’s family are some of Reilly’s most prominent real estate donors. Neil Bluhm, his son Andrew and daughter Meredith Bluhm each gave $17,000 to the Reilly campaign.
One of Reilly’s most impactful real estate donors is former Cinespace owner-turned-real estate investor and lender Alexander Pissios who gave the campaign $50,000. Other business community donors include trading and real estate investment firm DRW’s founder Don Wilson and Lettuce Entertain You restaurant group founder Rich Melman.
While Preckwinkle has courted fewer industry heavy-hitters than Reilly, she still secured some donations from prominent real estate names, including Capri Investment’s Quintin Primo and Clayco’s Michael Fassnacht. She has also enjoyed broad support from construction companies and trade unions like The Chicago Federation of Labor and the International Association of Operating Engineers.
Reilly has raised at least $609,000 since the start of 2026, when his campaign had over $1.2 million on hand, compared to Preckwinkle raising at least $480,000 raised since the start of the year, when she had more than $614,000 in campaign cash, according to state campaign finance reports.
The labor and business split is a departure from patterns seen in donations in the Cook County Tax Assessor’s race. Both groups are coalescing around challenger Patrick Hynes instead of incumbent Fritz Kaegi, a recent analysis by The Real Deal found.
Both Kaegi and Preckwinkle are supported by progressive organization Citizens Action Illinois. But Preckwinkle hasn’t faced as much public scrutiny as Kaegi, who has borne the brunt of the blame from real estate investors frustrated by wild fluctuations in Cook County tax bills since the pandemic. Preckwinkle also secured a $150,000 donation from Governor J.B. Pritzker.
Further, she commissioned a study of Chicago’s property tax system more broadly with a goal of making the process more predictable for investors and homeowners alike. Kaegi has said he supports the recommendations in the study, which includes improving communication and data sharing between the tax assessor and the Board of Review so that initial assessments and appealed assessments don’t vary as widely as they do now.
Meanwhile, Reilly, a moderate Democrat on Chicago City Council, is running a critical campaign against Preckwinkle amid backlash against progressives more generally. As Chicago’s progressive Mayor Brandon Johnson struggles to maintain support, real estate figures have been strategizing ways to regain influence in local politics.
Reilly has tried to pin blame on Preckwinkle for recently blown deadlines during a technology update for Cook County’s property tax data and billing systems that severely delayed tax bills. The systemic setbacks causing the late tax bills forced local school districts to incur steep interest costs on loans while they waited for their share of tax revenue.
Reilly even suggested he would cancel the county’s long-running contract with Tyler Technologies — the firm tasked with the tech upgrade — if the delays persist.
Preckwinkle has pushed back against this narrative, noting that the property tax system is a multi-agency effort involving other independently elected officials, like the assessor and treasurer, who handle valuations and billing. She maintains that the solution lies in collaborative problem-solving rather than finding fault or attacking colleagues in other departments.
Her supporters point out she hasn’t raised Cook County’s portion of the property tax levy for her entire tenure, nearly 16 years.
Whoever wins the March primary is expected to win the general election in November because Cook County is considered a safely Democratic county.