Mark Glennon: Chicago Office Buildings Losing 90% of Value While City Occupancy Rates Lag Far Behind Recovering Markets

New York Mayor Zohran Mamdani used his first hundred days in office sit-down interview with Meet the Press to invoke Tupac as a social scientist in defense of his spending priorities, arguing that America always finds money for war but not to feed the poor.

Mark Glennon, founder of Wirepoints, joined Dan Proft on Chicago’s Morning Answer to note that the federal government spent more than a trillion dollars on anti-poverty programs in fiscal year 2025 alone, roughly thirty thousand dollars per person below the poverty line, that two-thirds of the entire federal budget goes to social welfare and education compared to eight percent for the military, and that the Illinois state budget has grown forty percent over the last eight years to fifty-four billion dollars. The outcomes for the people these programs are supposed to serve have not kept pace with the spending, he said, and nobody in the political class running these cities and states wants to have that conversation.

Glennon said the Soviet comparison that Fox Business correspondent David Asman raised from his reporting in the dying USSR and its Eastern European satellites in the 1980s resonates precisely because Ukrainians who lived through that system understand it viscerally, which is part of what is motivating them to fight and die rather than submit to Putin’s Russia. He said he is traveling to western Ukraine next month, entering through Poland since there is no commercial air service into the country, to assess firsthand where humanitarian needs are most acute and where he might be able to contribute in some small way. He said the story of Ukraine’s war effort is developing faster than the American press is covering it, with Ukraine stabilizing the front lines, pounding the Russian economy, and gaining the upper hand on Russian deep strike capabilities. He said he expects western Ukraine, where he will be based, to be entirely safe.

Back in Illinois, Glennon addressed a proposal from State Representative Cam Buckner that would create what is being called a mega projects bill, allowing large commercial and industrial developments to negotiate their property tax bills with local governments. The immediate application being discussed is sweetening the deal for the Chicago Bears to build their new stadium in Arlington Heights by giving the team the ability to renegotiate its property tax obligations with the municipality. Glennon said the concept amounts to giving negotiating power to the biggest and most politically connected players while passing the resulting property tax shortfall down to homeowners and smaller commercial property owners who have no equivalent leverage. He said the fact that this is even being discussed as a necessary inducement illustrates how punishingly high commercial property taxes in Cook County and Illinois generally have become, and that high property taxes are a particularly bad mechanism for raising government revenue precisely because they create this kind of distortionary dynamic in major investment decisions.

The commercial real estate picture in Chicago that emerged from a series of recent building sales tracked by a commercial real estate analyst on social media tells a story that Glennon said is particularly bad by national standards. A building at 401 South State bought for sixty-eight million dollars in 2016 recently sold for four point two million. A property at 300 West Adams purchased for fifty-one million in 2012 sold for four million. One hundred North Riverside went from one hundred and sixty-five million in 2005 to twenty-two million. One seventy-five West Jackson fell from three hundred and six million in 2018 to forty-one million. Three eleven South Wacker dropped from three hundred and two million in 2014 to forty-five million. The losses across the portfolio run from roughly eighty-five to ninety-four percent in nominal terms.

Glennon said while the commercial real estate contraction following the work-from-home shift has affected cities broadly, Chicago is at the low end of recovery. Office occupancy rates based on actual card swipe data show Austin, Texas back to approximately eighty percent of pre-pandemic levels, while Chicago is still hovering around fifty-five percent with only a slight uptick over the past year. He said the doom loop dynamic, named by academics studying urban fiscal decline, is still operating in Chicago and is likely to get worse before it gets better. As collapsed commercial property valuations flow through to lower assessed values and lower tax bills for those buildings, the shortfall gets redistributed to residential property owners in neighborhoods like Englewood and West Garfield Park that are already reeling from the property tax bills they received last December, completing the cycle in which the fiscal consequences of the city’s broader dysfunction fall hardest on those least able to absorb them.

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