On Chicago’s Morning Answer, Dan Proft opened his weekly conversation with Wirepoints founder Mark Glennon by highlighting an exchange that captured, in his view, the city’s political dysfunction in miniature. A Chicago police officer was shot in Morgan Park over the weekend—saved only by the bulletproof vest he purchased himself—yet the question posed to Mayor Brandon Johnson by WTTW’s Heather Cherone focused not on the officer’s safety, nor on the violent offender whose struggle triggered the shot, but on whether an increase in police use-of-force cases might threaten progress under the federal consent decree.
For Proft, the framing symbolized a press corps and political class unable or unwilling to confront Chicago’s actual public-safety crisis. With 1,861 Chicagoans shot so far this year, including 410 homicides, he argued that obsessing over 21 police-involved shootings is a fundamental failure of perspective. Glennon agreed, calling Cherone’s line of questioning “astounding” and reflective of a media ecosystem—and a donor network behind it—that has grown increasingly detached from the lived experience of most residents.
That detachment, Proft noted, extends to the city’s political leadership. From the revolving-door release of violent offenders under the SAFE-T Act to permissive attitudes about undocumented criminals residing in Illinois, he argued that Chicago’s elected officials consistently place ideology ahead of the safety of law-abiding citizens. Glennon added that most casual news consumers, relying on a few minutes of public television or headlines from major papers, are “living in an alternate universe,” unaware of the severity of the problems.
The conversation then turned to the city’s looming budget showdown—characterized as a potential “government shutdown,” a first in Chicago history. But Glennon dismissed the drama as largely theatrical. The dispute between Mayor Johnson and the City Council, he said, centers on a narrow disagreement over a proposed corporate head tax, not on any structural reform that would alter Chicago’s long-term financial trajectory. Whether the city sprints or strolls toward fiscal collapse, he argued, it is “lost” under current leadership.
Proft pointed out that even as the city faces soaring pension costs, declining population, and deteriorating services, a new University of Chicago poll shows majorities of residents want more funding for Chicago Public Schools. Support was highest for corporate tax hikes, increased real-estate transfer taxes on properties over $500,000, and even a new city income tax on individuals earning more than $100,000. For Glennon, the numbers reflect decades of messaging that more spending automatically improves outcomes—despite CPS now spending $33,000 per student, more than double what countries like Sweden invest.
Still, Glennon sees a faint glimmer of opportunity in the recent uproar over skyrocketing property-tax bills in neighborhoods like Lawndale, Englewood, and West Garfield Park. Residents hit with 50 to 100 percent tax hikes in a single year are beginning to question long-standing political assumptions, including the Chicago Teachers Union’s outsized influence. Whether that awakening can be channeled into meaningful reform remains an open question.
But the stakes are unmistakable, Glennon said. The city’s budget debate is effectively a fight between progressives and “the head of the progressive caucus”—a choice between accelerating or merely continuing the decline. Meanwhile, leadership in City Hall and Springfield continues to focus on narratives and abstractions while violence persists, police go unsupported, and the city edges closer to insolvency.
For Proft and Glennon, the pattern is unmistakable: until Chicago’s political and media class confronts basic realities, the city’s downward trajectory will continue—no matter how many hours are spent in closed-door budget meetings or how many reporters frame police officers as the primary public-safety concern.