Chicago's 2025 Tax Squeeze

In the scorched aftermath of the Civil War, a shadowy opportunism took root in the American South. Northern interlopers, derisively called "carpetbaggers" for their cheap suitcases stuffed with get-rich schemes, descended on the region with promises of progress and partnership.

Often allying with newly freed Black Americans, these outsiders positioned themselves as saviors—only to exploit the chaos of Reconstruction for personal gain. High taxes imposed by these Reconstruction governments, meant to rebuild and educate, instead crushed Southern landowners under unbearable burdens, forcing sales of family farms at fire-sale prices.

Freed slaves, promised "40 acres and a mule" as reparations for centuries of bondage, watched their hard-won plots slip away through scams, debt peonage, and tax defaults.

Today, echoes of that betrayal reverberate in the Windy City. Chicago's leaders—Mayor Brandon Johnson and Governor JB Pritzker—are engineering a modern squeeze on working families, hiking property taxes to unsustainable levels and paving the way for foreclosures that strip equity from longtime homeowners. It's the same game: tax the vulnerable into submission, then let the vultures pick the bones.

The Ghosts of Reconstruction: How Taxes Stole the South

The Reconstruction era (1865–1877) was billed as America's grand redemption—a chance to stitch the nation back together and uplift four million emancipated souls. But for many in the South, it was a heist disguised as healing.

Carpetbaggers, mostly opportunistic Northern politicians, bankers, and speculators, flooded Dixie with radical agendas. They formed alliances with freedmen, who were granted voting rights under the 15th Amendment, to seize control of state legislatures.

These coalitions passed progressive laws: public schools for Black children, infrastructure projects, and debt relief for the poorest. Noble on paper, but the funding? It came from sky-high property taxes—sometimes quadrupled overnight—to service war bonds and build new bureaucracies.

White Southern planters, already reeling from defeat and emancipation, couldn't keep up.

Taxes on cotton fields and homesteads ballooned, turning assets into liabilities. By 1868, in states like South Carolina, tax rates hit 3% of assessed value—triple the pre-war norm—prompting mass foreclosures. Land that once sustained generations sold for pennies, snapped up by the very carpetbaggers who'd engineered the levy.

Freed slaves fared worse. General Sherman's 1865 Special Field Order No. 15 had allocated 400,000 acres along the Georgia and South Carolina coasts to Black families—roughly 40 acres per household.

But President Andrew Johnson revoked it months later, returning the land to Confederate owners. Those who managed to buy plots through federal programs fell into sharecropping traps or tax scams. White speculators, sometimes posing as allies with a freedman in tow for legitimacy, would "help" with loans or filings—then foreclose when taxes mounted, pocketing the deeds.

The result?

By 1880, the average Black farmer owned just 2.5 acres, down from the promised bounty.

White supremacists, branded "Redeemers," eventually ousted the carpetbaggers through violence and fraud, but the damage was done: a cycle of poverty that lingered for generations.

Reconstruction's taxes weren't just fiscal policy; they were a weapon of dispossession.

Chicago's Tax Tornado: A Billion-Dollar Deficit Devours Dreams

Fast-forward 160 years, and Chicago is staring down its own Reconstruction reckoning.

The city's property taxes—already the nation's second-highest, more than double the U.S. average—are a millstone around homeowners' necks.

In 2025, the typical Illinois family shells out $5,096 annually, enough to fund a family vacation or emergency fund. But with inflation gnawing at wages and energy costs soaring, these bills are eviction notices in slow motion.

Mayor Brandon Johnson, a self-styled progressive elected on vows to protect the working class, kicked off 2025 with a bombshell: a proposed $300 million property tax hike to plug a $1 billion budget hole.

His pitch?

No layoffs for city workers, more funding for mental health and youth programs.

City Council aldermen balked, unanimously rejecting the increase in the final $17.1 billion budget passed in December 2024. But the reprieve is temporary.

Johnson's chief financial officer has already warned of another hike "likely" for 2026 to cover ongoing deficits.

Meanwhile, state-level policies under Governor JB Pritzker exacerbate the pain. Illinois lags behind every other state in reforming tax-sale laws, allowing private investors to buy delinquent tax liens and foreclose, siphoning $108 million in home equity since 2019 alone.

A 2023 Supreme Court ruling in Tyler v. Hennepin County deemed such practices unconstitutional wealth-stripping, yet Illinois lawmakers—beholden to Pritzker's Democratic machine—have dragged their feet on compliance.

The fallout is brutal. In Chicago, foreclosure filings spiked 15% in 2024, with Black and Latino neighborhoods hit hardest—mirroring the racial inequities of post-Civil War land loss.

Seniors, many on fixed incomes after decades in their homes, face the worst: unpaid taxes from one missed bill can trigger sales where investors pocket the full property value, leaving owners with crumbs. One proposed fix? A bill to waive taxes for 30-year homeowners, but it stalls in Springfield amid Pritzker's focus on corporate incentives and pension padding.

Johnson's task force, in a tone-deaf September 2025 report, urged annual hikes tied to inflation to "keep pace"—code for perpetual escalation.

The Modern Carpetbaggers: Johnson, Pritzker, and the Property Playbook

Make no mistake: Chicago's mayor and Illinois' governor aren't twirling mustaches in a dimly lit boardroom.

But their policies—framed as equity and investment—bear an uncanny resemblance to the carpetbaggers' sleight of hand. Johnson campaigns on "taxing the rich" via corporate head taxes, yet pivots to homeowners when deficits loom, breaking his no-hike pledge faster than a South Carolina cotton lien.

Pritzker, the billionaire scion turned governor, touts progressive wins like marijuana legalization and minimum-wage bumps, but his inaction on tax reform lets predatory investors—today's equivalent of Yankee speculators—feast on foreclosed bungalows.

Both lean on TIF districts (tax increment financing) to siphon levies from neighborhoods into developer slush funds, echoing Reconstruction's bond schemes that lined Northern pockets.

The parallel runs deeper. Just as carpetbaggers used freedmen's votes to legitimize their grabs, Chicago's leaders cloak hikes in social-justice rhetoric: funds for migrants, gun violence prevention, climate initiatives. Vital causes, sure—but at what cost?

When a Bronzeville widow loses her walk-up to a lien buyer because her taxes jumped 20% overnight, it's not progress; it's plunder.

And like the 40 acres yanked back by Johnson (the president, not the mayor), Chicago's "promise" of affordable housing evaporates under the weight of unaffordable assessments.

Breaking the Cycle: Before It's Too Late

History doesn't repeat, but it rhymes—loudly. The South's Reconstruction taxes didn't rebuild; they entrenched inequality, birthing Jim Crow's iron grip.

Chicago risks the same: a hollowed-out tax base, fleeing families, and a city of landlords over citizens. Voters must demand reform—cap hikes at inflation, overhaul tax sales, prioritize seniors and fixed-income folks. Johnson and Pritzker rode waves of hope to power; now, they surf on despair. If carpetbaggers taught us anything, it's that opportunists thrive in the fog of crisis.

Chicagoans, don't let your deeds become their luggage. Organize, vote, agitate. Your home isn't just property—it's legacy. Fight to keep it.

‍

Do you need powerful political campaign management?  Contact Fractional CMO/CTO for Chicago