Cook County Board President Toni Preckwinkle is displaying some familiarity with an old real estate adage: possession is nine-tenths of the law. The county owns a lot of land, and she made a move Thursday that could characterize federal agents as trespassers, should they engage in certain immigration enforcement activity.
A few hours after Preckwinkle signed an executive order banning ICE operations on county property, she again touted the capacity of real estate dealmaking to shape politics, albeit in a much different arena.
The takeaway: Preckwinkle understands how to wield real estate as a tool for creating, maintaining and checking power.
Whether she and other Chicago public officials properly use the tool is up for debate, of course. Take David Doig, who shared the stage with Preckwinkle late Thursday night as they each accepted awards in front of over 200 industry professionals at the annual Marshall Bennett Institute of Real Estate gala in developer Jeff Shapack’s Fulton Market office building at 167 North Green Street.
Preckwinkle lamented that Chicago housing development had fallen to low levels in recent years, which has sent rents skyrocketing to the fastest rates of growth in the nation.
But the optics of the event grow more complex when one scans Doig’s real estate philosophies. The developer-activist behind the firm Chicago Neighborhood Initiatives has real estate credentials anchoring him firmly in the trenches where policy meets capital. And he’s been outspoken about what he views as a broken process for financing affordable housing that has driven up costs at some projects closer to $1 million per unit, far more than the price at which the private development market can produce.
Doig’s résumé includes stints in former Mayor Richard M. Daley’s city planning department, oversight of park district projects and development leveraging New Markets Tax Credits, showcasing a deep and practical engagement with the real estate sector.
In a Crain’s Chicago Business opinion piece, he argued that the city needs a “homebuilding revolution” to offset decades of underproduction. He frames the issue not simply as a lack of subsidized housing but as systemic supply constraints: red tape, zoning inertia, capital stack complexity and developer risk must be rethought. He observes that building more middle-market units (with minimal public subsidy) may help “soak up” demand and ease pressure.
Likewise, a Chicago Tribune editorial on “How ill-conceived ‘affordable’ housing becomes unaffordable” critiqued programs that inadvertently drive up costs through overregulation or misaligned incentives. While not authored by Doig, the piece echoes his criticism of subsidy complexity and questions whether government-backed projects can remain affordable under heavy compliance burdens.
At the gala, juxtaposing Preckwinkle and Doig was not random. It showcased dueling yet potentially complementary narratives: Preckwinkle as a political boundary-setter, Doig as a policy implementer. But the contrast also sharpens doubts. If Preckwinkle’s sanctuary county order stakes moral territory, Doig’s work reminds us that real change requires negotiating markets, finance, regulation and on-the-ground execution.
Still, linking them also raises tension: can a leader publicly decry suppressed housing starts while simultaneously endorsing a symbolic anti-ICE order whose enforcement is uncertain? Doig’s presence offers a foil: development pragmatism facing political idealism.
The larger question lingers: will sanctuary-style orders meaningfully reshape immigrants’ lived security — or will they serve chiefly as rallying flags? And can developers like Doig, pushing for a supply breakthrough, overcome the structural inertia that keeps Chicago undershooting housing demand?
At the gala, the award winners themselves told a story of converging aspirations — but whether Chicago gains homes, equity or protection depends on what happens when the impact of rhetoric fades.