Matthew Holbrook, a special education teacher in Niles Township High School District 219, received $39,000 in taxpayer-funded dollars from selling t-shirts to the district, some of that after being told flatly in 2024 by the district’s administration to stop doing so, according to district documents.
In addition, an elementary school district, where Holbrook has served on the Board of Education since at least 2005, paid his company $69,000 for sports apparel in the five school years from 2021 to the present, according to records received in a Freedom of Information Act request. The superintendent told Pioneer Press the district has ended the practice.
At High School District 219, over the course of two years, Holbrook’s two companies charged $38,890 in three contracts with the district, according to district documents requested by Pioneer Press.
Holbrook did so without disclosing his financial interest to the district, in violation of the district’s policies. In November, the Board of Education voted to suspend Holbrook for three days without pay.
District 219’s Executive Director of Human Resources and Legal Services, Ray Chung, wrote to Holbrook on Nov. 4, summarizing the district’s investigation into Holbrook’s business practices and notifying him that any continued violations of Board policies or work rules would be grounds for dismissal.
A 2024 district audit found that Holbrook was an employee vendor. Holbrook received a letter from the district on Dec. 9, 2024, stating that the district was suspending his ability to do business with it because it violated the Board’s policy on favoritism, according to Chung’s letter.
On Jan. 31, 2025, Holbrook met with Assistant Superintendent for Business Jim Vreeland and then-Director of Operations Sarah Kowalski. At the meeting, Holbrook was directed to no longer sell apparel to the district, Chung’s letter said.
According to the district’s 2024 annual statement of affairs, Holbrook’s company Color Your Own Inc. received $21,044.
In the district’s 2025 annual statement of affairs, Color Your Own received $13,575.
However, the district found that Holbrook continued to do business with the district after the Jan. 31 meeting.
“You disregarded the December 9, 2024 email and January 31, 2025 directive to cease conducting business with the district through an external business operation. Additionally, you sought to evade that directive by deceptively continuing to conduct business with the District under a changed name and though a purported ownership involving [redacted]. You referred employees to Cathy Barry at the new t-shirt company without disclosing that Cathy is [redacted]. Lastly, you failed to disclose a financial interest in a company which does business with the District,” Chung wrote.
Holbrook was directed by the district to immediately disclose to it all businesses in which he or his immediate family have a financial interest.
According to state filings, Holbrook activated a new business, Sport Team Apparel LLC, on May 27. According to the district’s 2025 annual statement of affairs, Sport Team Apparel earned $4,270.00 from the district. Barry and Holbrook are listed as managers of Sport Team Apparel.
Holbrook is also the president of the Niles School District 71 Board of Education.
A records request to that district showed that Holbrook’s company Color Your Own was paid $7,802 in the 2021-22 school year, $21,649.90 in the 2022-23 school year, 12,973 in the 2023-24 school year, 18,306 in the 2024-45 school year and $8,091 in the 2025-26 school year, for a grand total over five years of $68,822.
Holbrook did not respond to a request for comment for this story.
John Kosirog, District 71 superintendent, sent the following statement to Pioneer Press: “The district did purchase apparel items from Mr. Holbrook. At the time, the district did not realize that this conflicted with vendor-related Board policy. The issue was recently identified, the practice was ended, and no further purchases will be made.”