Chicago’s Government Grocery Gamble and Tax Burden Under Fire

Dan Proft and Wirepoints President Ted Dabrowski dissected the mounting failures of big-government policy experiments in Illinois and beyond—zeroing in on city-run grocery stores, ballooning pension obligations, and the state’s persistent tax burdens.

The conversation opened with the struggles of a city-run grocery store in Kansas City, which despite initial fanfare, has seen customers drop from 14,000 to just 4,000 in seven years. Reports of crime, shoplifting, and poor conditions now plague the operation, even as the city continues to funnel taxpayer money into it.

“This is the government trying to run a grocery store like it’s a public utility,” Dabrowski said. “The idea that sentimentality alone can make a grocery store work is naïve—especially when basic functions like law enforcement and community safety are ignored.”

The comparison wasn’t lost on Chicago. Mayor Brandon Johnson’s proposal for a city-owned grocery store has drawn sharp criticism from fiscal conservatives, who argue that Chicago’s attention should be on creating an environment where private businesses can thrive, not on mimicking failed central planning models.

Proft and Dabrowski also turned their focus to the Chicago Transit Authority’s looming deficit, pegged at nearly $1 billion. With ridership still hovering at just 60% of pre-COVID levels, Dabrowski noted the absurdity of running empty or half-full trains simply to keep up appearances. Rather than restructuring, the state is reportedly considering a transfer tax increase that could raise suburban property transaction costs by 600%—a move Dabrowski warned would pile even more pressure on homeowners in a state already ranked near the top for property tax burdens.

“These are complex operations,” Dabrowski said. “Running a grocery chain or a transit network efficiently is hard even in the private sector. But when politicians throw taxpayer money at these without reforming the structure or incentives, you’re just digging a deeper hole.”

The conversation then shifted to pensions. Despite having the worst-funded police and fire pension systems in the country, Illinois lawmakers recently approved benefit increases for Chicago’s first responders. Dabrowski, while sympathetic to public safety personnel, warned that these unfunded promises are making the state’s long-term fiscal picture even more dire.

“Making promises you can’t keep is not kindness—it’s cruelty,” Dabrowski said. “It jeopardizes the very people you say you’re helping by making future payouts more uncertain.”

Finally, the duo discussed Illinois’ long-term real estate trends. While recent data shows a short-term spike in housing prices—driven largely by a lack of new construction—Illinois ranks near the bottom in long-term housing appreciation. Dabrowski pointed to a collapse in new housing units in Cook County and broader economic stagnation as reasons why the uptick may be short-lived without major policy shifts.

“There’s still demand in Chicago, but it’s being strangled by high taxes, crime, and poor governance,” Dabrowski concluded. “Without leadership that’s willing to confront these root issues, we’re just spinning our wheels.”

The conversation encapsulated a recurring theme in Dabrowski’s policy commentary: until Illinois changes its approach—from top-down planning to fostering real economic freedom—residents will continue to shoulder the cost of well-meaning but deeply flawed government initiatives.

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