Fighting4Freeport Exposes Property Tax Questions Surrounding Brian Stewart’s Holdings
Freeport, IL - April 14, 2025
In a town where every penny counts, property taxes are a key factor in maintaining the health of our community. And for Freeport, a troubling pattern has emerged regarding the property taxes of local businessman and investor Brian Stewart, whose company Stewart Centre LLC has owned several key properties in the city, including the landmark Stewart Centre.
For many Freeport residents, the Stewart Centre — a sprawling facility housing State Senator Andrew Chesney’s office, the Stephenson County Board Offices, and the County Clerk’s office — is more than just a large building. It’s become a symbol of Freeport and a “clubhouse” for the elite. After all, in 2006, the city watched with excitement as Stewart purchased the Stewart Centre building for $1.375 million.
However, the reality of how Stewart’s property tax bills have evolved since his purchase raises serious concerns.
A Shift in Property Tax Bills: A Pattern Emerges
From 2000 to 2005, the property taxes on the building located at 50 W. Douglas Street steadily increased, rising from $101,684.92 in 2000 to $108,527.09 in 2005. But upon Stewart’s acquisition of the property in 2006, the property tax bill took a sharp dive, dropping to $66,420.28 — a decrease of nearly 40%.
Since then, the taxes have continued to remain significantly lower than the levels they reached before Stewart’s purchase. The lowest point was $44,575.58 in 2007, and the highest was $63,912.70 in 2019. For context, before Stewart’s purchase, Freeport’s government and schools were receiving an average of $104,535 annually from the Stewart Centre’s property tax bill. Since Stewart took ownership, the average tax bill has dropped to just $57,581 — a reduction of nearly $47,000 per year over the past 19 years. In total, that’s an estimated $892,126 in property taxes that has not been paid to Freeport’s schools, county government, city services, parks, libraries, and even Highland College.
This money, of course, hasn’t disappeared. It’s simply been shifted onto the backs of the rest of Freeport’s residents, who must shoulder the burden of making up for the lost revenue through their own property taxes.
Tax Breaks on Multiple Properties
But the questions surrounding Brian Stewart’s property taxes don’t stop at the Stewart Centre. In 2011, Stewart Centre LLC acquired a second key property located at 750 Kiwanis Dr., which currently houses the VA Clinic. Again, the trend continued: property taxes on the building plummeted from $22,580 in 2010 to just $3,581 in 2011. Even as the property’s taxes increased over time, they never approached the levels seen prior to Stewart’s ownership, remaining consistently below $7,000 through 2019.
That’s a stunning 75% reduction in property taxes for Stewart over the course of eight years, while the rest of the community had to pick up the slack.
The Pearl City Road Property: A $1.25 Million Tax Break
If the pattern wasn’t concerning enough, in 2014 Stewart Centre West LLC purchased another high-profile property at 2900 Pearl City Rd. And once again, the property tax bills plummeted, dropping from $160,799 in 2013 to just $33,324 in 2014 — a difference of $125,000. Even in recent years, the taxes have remained significantly lower than they were before the property’s transfer, staying at or just above the $35,000 mark.
This reduction has resulted in a total loss of $1.25 million in property tax revenue over the past decade — money that would otherwise have gone to fund local schools, the city, the county, and other essential services. Instead, it’s been shifted onto the shoulders of regular residents who are seeing their own property taxes rise to make up for the shortfall.
The Bigger Picture: Why Freeport Isn’t Thriving
The ramifications of these ongoing tax reductions go far beyond just Brian Stewart’s individual properties. The lost revenue means that essential services and local institutions — from schools to libraries — have had to depend on ever-higher taxes from the rest of the population, leaving Freeport residents bearing an unfair burden.
The situation highlights a larger issue that many feel is contributing to the struggles of Freeport: a lack of accountability in local politics. With such tax breaks for wealthy investors and property owners, the city’s resources are spread thin. Local leaders are often reluctant to take on powerful figures in the community, and so Freeport’s residents continue to pay the price.
Stewart’s actions raise the question: is this a series of unfortunate mistakes, or is this simply a habit that some find too difficult to break?
Either way, the fact remains: Freeport’s working-class residents have been picking up the slack for too long. The city is not thriving as it should, and it’s clear that something needs to change.
As Freeport continues to face these challenges, Fighting4Freeport remains committed to shining a light on these issues, advocating for fair and equitable treatment for all residents, and holding those in power accountable. Our community deserves better.