Hinsdale High School District 86 taxpayers are caught in the middle of a legal battle that has already cost hundreds of thousands of dollars, with no end in sight.

The district and its former law firm, Chicago-based Robbins Schwartz, are now suing each other over who bears responsibility for the expensive 2023 departure of Superintendent Tammy Prentiss. Robbins Schwartz wants $228,000 in unpaid legal bills. District 86 filed a counterclaim alleging the firm's managing partner, Joseph Perkoski, gave contradictory advice that forced the board into a roughly $300,000 settlement with Prentiss and left it paying for interim superintendents.

The latest volley came in June 2026, when Robbins Schwartz filed a court brief asking a judge to throw out the district's counterclaim on statute-of-limitations grounds, arguing District 86 waited too long to sue.

District 86 attorney Gary Grasso said in an email that he was confident the firm's argument "was not well-founded" and that the district would respond.

What the district claims happened

The counterclaim, filed in spring 2026 according to Patch reporting from late April, lays out a timeline that starts with a phone call. According to the district's filing, Prentiss called board President Catherine Greenspon and disclosed that then-board member Debbie Levinthal and two other board members each had students with special needs.

In a closed session on June 26, 2023, Perkoski told the board that Prentiss violated no privacy laws because she had not revealed a specific diagnosis or student need. That advice meant the board lacked cause to fire Prentiss outright. Instead, the board settled. Prentiss agreed to leave and received a full year of pay and benefits, costing approximately $300,000.

Then, in August 2024, a different Robbins Schwartz attorney gave the opposite advice, telling the board that Prentiss had in fact broken the law even without revealing a diagnosis. The district says that contradiction proves Perkoski's original guidance was wrong and that the settlement was unnecessary.

Robbins Schwartz pushes back

In its June 2026 court brief, the firm argued the district cannot prove its case. Robbins Schwartz said board members disagreed with Perkoski's advice during that June 2023 closed session but that the district "fails to point to any specific excerpt of the alleged advice" in its filing.

The firm also argued the board was going to fire Prentiss regardless of the legal guidance and would have needed an interim superintendent either way. Therefore, Robbins Schwartz contends, the district cannot establish that the advice caused its financial losses.

The broader cost to taxpayers

The dollar figures keep adding up. Beyond the $300,000 Prentiss settlement and the $228,000 in disputed legal bills, the district paid $80,000 to settle a separate claim involving Levinthal's family, according to a Patch report published in May 2025. The district also spent on multiple interim superintendents after Prentiss left. According to Patch's reporting on the court filings, Robbins Schwartz was on track to bill the district $1 million in a single year before it terminated the relationship in September 2024, calling District 86 "unreasonably difficult" to serve.

Greenspon led the 2023 board majority that voted to part ways with Prentiss and hired Michael Lach as her replacement. The board later soured on Lach as well. Dr. Jack "Chip" Pettit joined as the district's new superintendent on Tuesday, July 1, 2026, ending a period of interim leadership that added to the district's expenses.

What's still unknown

No next court date, ruling deadline, or judge's name appears in available reporting on this case. The Robbins Schwartz brief is available on Scribd. Residents seeking additional records can file requests under the Illinois Freedom of Information Act (5 ILCS 140) with the district.

Hinsdale government week ahead

• Tuesday, August 25 — District 86 Board of Education meeting. The district's meeting schedule page was unavailable at publication; check hinsdale86.org for agenda posting and public comment details.