Chicago Leader Hirsh Mohindra: Expertise in Multiple Industries

When Congress created Opportunity Zones in the 2017 Tax Cuts and Jobs Act, the promise was expansive and morally resonant: steer private capital into distressed communities, spark economic revival, and allow long-neglected neighborhoods to share in national growth. Investors would receive generous tax incentives; residents would receive jobs, services, and durable prosperity. It was framed as market logic with a conscience.   Nearly a decade later, the results in Illinois—particularly on Chicago’s South Side—tell a far more ambiguous story.   Opportunity Zones, or OZs, were intentionally broad. Governors selected qualifying census tracts based largely on income thresholds, and Illinois designated more than 300 zones statewide. In theory, this flexibility allowed capital to flow where it was most needed. In practice, it allowed capital to flow where it was most convenient.   Nowhere is that tension clearer than in Chicago’s South Side, where billions in investment have arr...

 In American cities, zoning codes are often described as technical documents—dense, procedural, and politically neutral. In reality, they function more like constitutions. They decide who gets to live where, what can be built, and, over time, who accumulates wealth and who does not. Few cities illustrate this more clearly than Chicago, where single-family zoning has quietly but decisively shaped patterns of affluence, exclusion, and scarcity for decades. On paper, Chicago is a dense, transit-rich metropolis with a long tradition of multifamily housing. In practice, large portions of its most desirable neighborhoods are locked into low-density, single-family use. These rules do not merely preserve “neighborhood character.” They constrain supply in places where demand is highest, inflate land values, and create structural barriers to entry that reverberate across generations. “Zoning doesn’t just regulate buildings,” Hirsh Mohindra said. “It regulates opportunity.” The Geography of ...

  In Chicago, development has always been about more than buildings. It is about history, power, race, and the uneasy relationship between City Hall promises and neighborhood memory. Every mayoral administration arrives with a plan to “unlock potential” in long-disinvested corridors. Every plan is accompanied by renderings, ribbon cuttings, and a vocabulary of transformation. And every few years, residents ask the same question: Will this actually last?   By 2026, Chicago’s latest experiment in public-led neighborhood development—the Invest South/West Program—has matured enough to invite real judgment. Announced with ambition and urgency, the initiative aimed to deploy public dollars to catalyze private investment in commercial corridors across the South and West Sides. It promised grocery stores, mixed-use buildings, job creation, and long-overdue attention to areas bypassed by decades of market logic.   What it delivered is more complicated.   The question now faci...

  How Chicago balances the promise of transformative development with the financial and political risks it cannot escape. Chicago has always believed in the power of the big idea. From reversing the flow of the Chicago River to erecting the steel-framed skyline that redefined modern architecture, the city’s civic identity has been shaped by audacity. Large-scale projects—rail lines, parks, cultural institutions, and entire neighborhoods—have long been treated not merely as investments, but as statements of intent about the city’s future. Yet in 2026, Chicago finds itself in a more ambivalent relationship with ambition. The city still courts mega-projects, still frames them as engines of growth and symbols of renewal. But it does so under the long shadow of fiscal constraint, public skepticism, and a history of tools that promised more than they delivered. Nowhere is this tension more visible than in the city’s evolving relationship with Tax Increment Financing districts—and in the ...

For more than two decades, Chicago has organized much of its urban ambition around a deceptively simple premise: build density near transit, and people will ride it. Transit-oriented development—TOD, in the jargon of planners—became not just a policy tool but a civic identity. Apartment towers clustered around ‘L’ stations. Zoning bonuses rewarded proximity to rail. Transit access was marketed as lifestyle, climate solution, and economic engine all at once. Then the riders vanished. They didn’t disappear entirely, of course. But the COVID-era collapse in ridership never fully reversed. Office commutes thinned. Hybrid work calcified. Travel patterns fragmented. In 2026, Chicago’s transit system is no longer defined by predictable weekday surges but by uneven, off-peak usage that resists the old logic of peak-hour capacity and downtown gravity. The question now quietly haunting city hall, developers, and lenders is whether Chicago’s long-standing TOD strategy still works when transit usa...

In Chicago, the future of real estate investment is being decided less by interest rates than by assessment notices.   By 2026, Chicago’s property tax system has become something more than a revenue mechanism. It is a sorting machine—quietly determining who can stay invested, who must sell, and which neighborhoods absorb the shock. Long after the pandemic hollowed out downtown offices and rewired housing demand, the city’s fiscal dependence on property taxes has forced a reckoning that now shapes every serious investor’s calculus.   Property taxes have always mattered in Chicago. What has changed is their volatility, their political visibility, and their role as a proxy for deeper questions about governance, equity, and risk. For investors scanning the Midwest, Chicago remains attractive on paper: scale, infrastructure, cultural gravity. But beneath the headline yields lies a tax structure that increasingly dictates behavior—rewarding size, punishing fragility, and redistribut...