CHICAGO, September 7, 2026 – Addressing the media from the press room located on the fifth floor of 121 North LaSalle Street on Tuesday, Mayor Brandon Johnson appeared less like the experienced CEO of a metropolis and more like a high school teacher trying to maintain order among unruly students during a class. For this ex-Chicago Teachers Union organizer, whose path to City Hall was fueled by popular excitement, being mayor of the country’s third-largest metropolis is no picnic, politically speaking.
It does matter, however, since Johnson was promising a completely different path – a progressive policy approach that would finance social security systems through corporations’ tax payments and not through austerity.
However, after 18 months of his presidency, the plan faces a financial crisis worth about $1 billion. Given the ever-increasing financial obligation from the municipal pension, the cost of care for remaining migrants, and reduced funding from the Federal government in fighting the pandemic, City Hall’s financial record has become rather poor. In closing the budget gap, the finance policy of the city administration is based mainly on raising revenues through the “Bring Chicago Home” real estate transaction tax reform program intended to charge taxes on commercial transactions worth over $1 million in order to fund the homelessness prevention program, among others.
The challenge is that Johnson’s main progressive group, the organizers and labor union activists who got him elected to office, expects him to stick to progressive commitments while the moderate City Council Members require fiscal responsibility.
The business community down LaSalle Street has sounded loud and clear red alerts regarding these tax proposals, warning that heavy taxation policies will only cause companies to flee Chicago and result in further office vacancy in the city center. Meanwhile, the 50-member city council has become ideologically divided. Although the Progressive Caucus strongly supports his “treatment not trauma” crime prevention policies and youth employment programs, moderate and conservative members have tried several times to block any voting on those policies by insisting on a ceiling on spending and an increase in police funding.
“This is not the conversation that you were having 10 years ago,” Johnson declared during a sit-down interview, framing his budget governance as an ideological pivot. “We were talking about cuts, closures, consolidations, efficiencies, austere budgets that have been brought to us by neoliberals… We have clearly turned the page.
His government remains supportive of funding youth employment schemes, psychological centers, and the creation of affordable housing facilities. However, pushing these policies through an ever-splitting council has become an extremely challenging ordeal, with even regular committee votes degenerating into lengthy floor battles.
No one is really sure if Johnson can fill the widening gap prior to the budget deadline, when he will be left with no choice but to act.
From top to bottom at City Hall, the senior aldermen whisper about the tensions between the executive and the legislative branches, citing high-profile staff turnover in the mayor’s camp as evidence of the growing pains. On the other hand, community groups on the West Side in areas like Austin and Garfield Park have remained cautiously optimistic about Johnson sticking to his main campaign promises despite the media’s insistence on focusing only on conventional policing.
The political soap opera unfolding in Chicago is part of a larger challenge for the nation’s progressive mayors in showing that they have the skill to run a big city bureaucracy while implementing reforms.
For Johnson, who faces what will be his biggest legislative struggle yet, the issue isn’t whether he has an ambitious political vision; rather, it is whether he can get the money to implement it without alienating the very city that he promised to change when he ran for office.
