Questions about free speech, taxation, and the direction of city policy took center stage as radio host Dan Proft spoke with Mark Glennon, founder of Wirepoints, during a wide-ranging discussion on the state of governance in Chicago and Illinois.
The conversation followed a national news report involving an elementary school teacher in suburban West Chicago who was placed on leave after posting a pro–law enforcement message on social media. Proft and Glennon contrasted that response with a separate state-backed investigation into a landlord accused of cooperating with federal immigration authorities, arguing that the two cases illustrate what they see as uneven enforcement of civil rights and First Amendment protections. Glennon described the disparity as emblematic of a broader shift toward government actions driven more by politics than by consistent application of the law.
Attention then turned to Chicago Mayor Brandon Johnson’s recent remarks defending his fiscal agenda. Johnson has repeatedly argued that the city does not have a spending problem but rather a revenue problem, and has pledged to continue pressing for progressive taxes despite previous failures at the City Council and at the ballot box. In a televised interview, the mayor likened his pursuit of new revenue streams to historic civil rights struggles, a comparison Proft and Glennon dismissed as hyperbolic.
Glennon said the mayor’s insistence on revisiting rejected tax proposals ignores a deeper issue of public trust. He argued that voters and businesses have grown unwilling to approve new taxes not because of who would pay them, but because of skepticism over how additional funds would be managed. He pointed to the statewide rejection of a graduated income tax amendment as evidence that even progressive-leaning voters are wary of granting government broader taxing authority.
Chicago Public Schools were another focal point. Despite declining enrollment and billions of dollars in long-term debt, Johnson has called for increased investment in CPS, including higher teacher pay and expanded staffing. Glennon countered that the district already spends far more per student than national and international averages, and that shrinking utilization rates at many schools undermine claims that funding levels are insufficient. He warned that labeling ever-higher spending as “investment” obscures the lack of measurable returns in student outcomes.
The discussion also touched on the city’s broader tax climate. Glennon cited Wirepoints research showing that Chicago has the highest commercial property tax rate among the nation’s largest cities, a burden he said is ultimately passed on to residents through higher rents and prices. He argued that continued reliance on tax hikes risks accelerating population loss and business flight, further eroding the city’s tax base.
Throughout the exchange, both men framed the debate as a referendum on governance rather than ideology. Glennon said the pattern of expanding government authority, selective enforcement, and persistent calls for new revenue reflects a political culture increasingly detached from fiscal realities. Proft added that the repeated use of moral language to justify tax increases and regulatory actions masks what many residents experience as declining services and rising costs.
As Chicago leaders prepare for future budget fights and elections, the interview underscored a growing divide between City Hall’s vision and a segment of the public that questions whether more money and more power for government will resolve the city’s long-standing challenges.