Mayor Johnson’s Tax Blitz: Is Chicago Chasing Away Its Future?

Paul Riverbank, 12/16/2025Chicago’s tax hikes spark fierce debate over spending, business, union power, and future priorities.

“It’s a case of the bill coming due,” Grant McClintock, a budget analyst at the Civic Federation, pointed out the other day. He described the city’s financial math as a puzzle missing several key pieces, an image that resonates as everyday residents watch programs linger but the money that supported them vanish.

But Mayor Brandon Johnson is digging in, not retreating. Instead of slashing spending, he’s staking the city’s future on a raft of new taxes. One of them, the “personal property lease tax,” could soon climb from 11% to 14%. Rent a car downtown, license new software for a small business—expect to pay extra. Johnson also wants to resurrect the infamous “head tax”—$33 for each employee, each month—targeted at the biggest companies. Critics, including The Post’s editorial board, predict a mass exodus of businesses and fewer jobs. Their skepticism could fill a stadium: “By making it more expensive to do business or hire workers in the city, these measures threaten Chicago’s future economic growth and tax collections,” they warned.

Mayor Johnson, unbowed, claims most of the tax burden will fall on the city’s corporate behemoths—less than one percent of businesses, by his count. Boosters in his camp like to cite groups such as the Civic Federation, which has occasionally shown sympathy for his approach. Yet the political calculus is tricky; the federation has also warned about not fully funding pensions, while grudgingly branding the “community safety surcharge” as a “legitimate option.” In other words: support is patchy, conditional, and never quite complete.

It’s not just about raising rates, either. To keep things afloat, the city has used a mix of what can charitably be called “creative accounting.” Hiring freezes have been imposed, then quietly lifted. Money tagged for blight clean-up gets diverted to pay everyday bills. One particularly troubling move: trimming extra pension payments, a change that helps for now but may bring far greater pain down the line. The analogies write themselves—one alderman compared it to “selling off the roof tiles just to pay the plumber.”

There’s a deeper, thornier dynamic at play, too—namely, organized labor’s clout. The Chicago Teachers Union (CTU) has steadily expanded both its ranks and its political muscle. Since 2010, the schools’ budget has swelled from $6.9 billion to nearly $10 billion. Curiously—and this is the statistic that keeps popping up—since 2019, the district has picked up 9,000 new full-time jobs, despite a shrinking student population. Conversely, the headcounts for city police, fire, and other essential services have dropped by more than 2,000. This lopsided growth isn’t lost on residents, who wonder if educational spending is coming at the expense of the services that keep their neighborhoods safe and functional.

The teachers union’s ascent has triggered unease elsewhere. The SEIU (Service Employees International Union), for one, accuses the CTU of “raiding” its members, further stoking tensions among public-sector workers who until recently tended to band together. There’s a scramble for influence, for dues, for a seat at the table where the city’s future is being mapped out. Former mayoral candidate Paul Vallas put it bluntly: “The CTU has evolved into an existential threat to Chicago’s fiscal health—and to the city’s other public sector unions.” For him, what’s at stake is not just budgets, but the very machinery of city government.

Meanwhile, homeowners and longtime city employees are increasingly restive. With property taxes climbing year after year, the value proposition feels increasingly murky. In private, some city workers will admit they send their own kids to private schools, no longer trusting a public system that seems to be growing more expensive but not necessarily better. For ordinary families—those priced out of private tuition or selective magnet programs—the frustration is real, even raw. Every tax hike and budget vote at City Hall ripples outward: into classrooms, onto city streets, and back into household budgets.

The reaction at the grassroots has been swift and varied. Several aldermen, rejecting the mayor’s blueprint, have drawn up their own competing budgets. There’s talk of higher garbage fees, but the mayor has promised a veto if that gets traction. The surface struggle is over numbers, but the real dispute runs deeper—about priorities, about whether the path forward means ever-more spending on education or a pivot back toward neglected public safety and basic services.

For all the headlines and heated arguments, Chicago’s predicament is stark in the end. There’s no shortcut—only tough trade-offs between sustained spending, fresh revenue, and deep cuts. As the city stands at this crossroads, two things will matter above all: leadership willing to square up to hard truths, and a public realistic enough to demand better. Chicagoans, as ever, await their answer.

Chicago’s budget debates have always had their share of drama, but this season feels especially charged. In City Council, tempers flare; in neighborhood bars, the conversation turns, inevitably, to taxes. For some, things have gone off the rails—a sentiment loudly echoed in an editorial from The Washington Post, which recently accused the Windy City of “losing its mind” on spending. The accusation stings, but the numbers back up the worry: since 2019, the city’s operating budget has ballooned by almost 40%. Federal dollars that once made the bloat possible have run dry. What those funds built, however, hasn’t gone away.“It’s a case of the bill coming due,” Grant McClintock, a budget analyst at the Civic Federation, pointed out the other day. He described the city’s financial math as a puzzle missing several key pieces, an image that resonates as everyday residents watch programs linger but the money that supported them vanish.But Mayor Brandon Johnson is digging in, not retreating. Instead of slashing spending, he’s staking the city’s future on a raft of new taxes. One of them, the “personal property lease tax,” could soon climb from 11% to 14%. Rent a car downtown, license new software for a small business—expect to pay extra. Johnson also wants to resurrect the infamous “head tax”—$33 for each employee, each month—targeted at the biggest companies. Critics, including The Post’s editorial board, predict a mass exodus of businesses and fewer jobs. Their skepticism could fill a stadium: “By making it more expensive to do business or hire workers in the city, these measures threaten Chicago’s future economic growth and tax collections,” they warned.Mayor Johnson, unbowed, claims most of the tax burden will fall on the city’s corporate behemoths—less than one percent of businesses, by his count. Boosters in his camp like to cite groups such as the Civic Federation, which has occasionally shown sympathy for his approach. Yet the political calculus is tricky; the federation has also warned about not fully funding pensions, while grudgingly branding the “community safety surcharge” as a “legitimate option.” In other words: support is patchy, conditional, and never quite complete.It’s not just about raising rates, either. To keep things afloat, the city has used a mix of what can charitably be called “creative accounting.” Hiring freezes have been imposed, then quietly lifted. Money tagged for blight clean-up gets diverted to pay everyday bills. One particularly troubling move: trimming extra pension payments, a change that helps for now but may bring far greater pain down the line. The analogies write themselves—one alderman compared it to “selling off the roof tiles just to pay the plumber.”There’s a deeper, thornier dynamic at play, too—namely, organized labor’s clout. The Chicago Teachers Union (CTU) has steadily expanded both its ranks and its political muscle. Since 2010, the schools’ budget has swelled from $6.9 billion to nearly $10 billion. Curiously—and this is the statistic that keeps popping up—since 2019, the district has picked up 9,000 new full-time jobs, despite a shrinking student population. Conversely, the headcounts for city police, fire, and other essential services have dropped by more than 2,000. This lopsided growth isn’t lost on residents, who wonder if educational spending is coming at the expense of the services that keep their neighborhoods safe and functional.The teachers union’s ascent has triggered unease elsewhere. The SEIU (Service Employees International Union), for one, accuses the CTU of “raiding” its members, further stoking tensions among public-sector workers who until recently tended to band together. There’s a scramble for influence, for dues, for a seat at the table where the city’s future is being mapped out. Former mayoral candidate Paul Vallas put it bluntly: “The CTU has evolved into an existential threat to Chicago’s fiscal health—and to the city’s other public sector unions.” For him, what’s at stake is not just budgets, but the very machinery of city government.Meanwhile, homeowners and longtime city employees are increasingly restive. With property taxes climbing year after year, the value proposition feels increasingly murky. In private, some city workers will admit they send their own kids to private schools, no longer trusting a public system that seems to be growing more expensive but not necessarily better. For ordinary families—those priced out of private tuition or selective magnet programs—the frustration is real, even raw. Every tax hike and budget vote at City Hall ripples outward: into classrooms, onto city streets, and back into household budgets.The reaction at the grassroots has been swift and varied. Several aldermen, rejecting the mayor’s blueprint, have drawn up their own competing budgets. There’s talk of higher garbage fees, but the mayor has promised a veto if that gets traction. The surface struggle is over numbers, but the real dispute runs deeper—about priorities, about whether the path forward means ever-more spending on education or a pivot back toward neglected public safety and basic services.For all the headlines and heated arguments, Chicago’s predicament is stark in the end. There’s no shortcut—only tough trade-offs between sustained spending, fresh revenue, and deep cuts. As the city stands at this crossroads, two things will matter above all: leadership willing to square up to hard truths, and a public realistic enough to demand better. Chicagoans, as ever, await their answer.