“We’re Being Taxed Out”: Freeport Families Struggle Under Crushing Property Tax Burden While Political Insiders Profit
May 10, 2025
When one Freeport homeowner opened her 2024 property tax bill and saw it had jumped to over $2,300, she felt disbelief.
“That’s more than a mortgage payment for some people,” she said. “And I still have a leaking roof and a cracked sidewalk. What am I paying for?”
It's a question many in Freeport are asking, as residents face some of the highest effective property tax rates in the nation—2.2% on a median home value of $86,500—while public infrastructure and services continue to deteriorate.
But what’s emerging now is a deeper frustration: while everyday families are being squeezed, politically connected insiders and large property owners appear to be getting a break.
One name that keeps surfacing is Brian Stewart, former state senator and owner of the Stewart Centre downtown. Stewart, through a network of LLCs, owns numerous properties in Freeport—and public records reveal he’s benefited from millions in property tax reductions, exemptions, and valuation appeals over the past decade. As his tax liability has gone down, the overall levy hasn’t—it’s just been shifted to regular homeowners.
“We’re subsidizing the very people who have the connections to get out of paying their fair share,” said one local property owner who reviewed county tax appeal records. “It’s legalized favoritism.”
Meanwhile, Highland Community College approved a 12.8% increase to its tax levy in December 2023—bringing in nearly $14.7 million, up from $13 million the year before. The added burden falls squarely on property taxpayers.
Even more surprising is who’s applauding it: State Senator Andrew Chesney, a self-described “fiscal conservative” who frequently criticizes government spending, has been openly supportive of Highland and its funding. At the same time, he supports Freeport Mayor Jodi Miller, who cast the deciding vote to increase the city’s sales tax to 9%—one of the highest rates in the region.
“Chesney claims to stand for the taxpayer, but he’s backing the very policies and politicians that are bleeding us dry,” said a frustrated resident.
City Manager Rob Boyer defended the 1% sales tax hike, calling it necessary to repair crumbling roads, noting a decline in motor fuel tax revenue. But small business owners aren’t buying it.
“Every tax increase hits not just our margins, but our customers’ wallets,” said Sam Cimino, owner of Cimino’s Little Italy, in an interview with WIFR. “At some point, people stop going out.”
The tension reflects a broader statewide trend: Illinois has suffered ten straight years of population decline, with high taxes being one of the top reasons people pack up and leave.
Now, Freeport residents are asking harder questions—about fairness, equity, and whether local leadership is working for the people or the power brokers.
“We’re not going to keep footing the bill while services decline and the politically connected walk away with tax breaks,” the homeowner said. “The system’s rigged, and we’re done staying quiet about it.”
Fighting4Freeport will continue exposing local tax abuse and holding decision-makers accountable. If you have information about property tax favoritism or insider deals, contact us confidentially at Fighting4Freeport@gmail.com.
