Legal Showdown: Hinsdale District 86 and Former Lawyers Lock Horns Over Superintendent's Ouster Advice

Oh, the tangled webs we weave, especially when it comes to legal advice and high-stakes decisions. That's precisely the drama unfolding right now in Hinsdale, where High School District 86 finds itself embroiled in a rather messy legal spat with its former legal eagles, the Robbins Schwartz law firm. What began as a dispute over unpaid bills has, frankly, spiraled into a much bigger saga, with the district pointing fingers and claiming 'bad advice' cost them dearly during the ouster of their former superintendent.

The whole thing really kicked off when Robbins Schwartz, a Chicago-based firm, initially sued District 86 for a cool $228,000 in what they claimed were overdue invoices. But District 86, it seems, wasn't about to just pay up quietly. Instead, they hit back with a counterlawsuit a few months ago, alleging that the firm's counsel regarding the departure of Superintendent Tammy Prentiss was, well, flawed. And not just a little flawed, mind you, but 'bad advice' that ultimately cost the taxpayers "hundreds of thousands of dollars." We're talking about a significant chunk of change here, including an approximate $300,000 settlement for Prentiss – essentially a full year's pay and benefits – plus all the extra costs of bringing in interim superintendents while they searched for a permanent replacement.

Let's rewind a bit to understand the heart of this particular legal storm. Back in June of 2023, Joseph Perkoski, an attorney from Robbins Schwartz and the primary legal advisor to the District 86 board at the time, was central to the discussions about Superintendent Prentiss. The issue at hand involved accusations that Prentiss had, shall we say, overshared some information, specifically revealing that board members Debbie Levinthal and two others had students receiving special education services. The board, quite naturally, was concerned about potential privacy law violations.

Here's where the advice becomes critical. Perkoski's counsel, according to the court filings, was that Prentiss hadn't actually violated any privacy laws because she hadn't disclosed specific diagnoses, only the fact that the students were receiving special needs services. This meant, crucially, that the board lacked a solid "cause" to fire Prentiss outright. And because they couldn't fire her for cause, the path led straight to that hefty settlement. It's interesting to note, too, that some board members, including President Catherine Greenspon, reportedly voiced their disagreement with Perkoski's assessment during a closed session on June 26, 2023. You can imagine the tension in that room.

But the story doesn't end there, oh no. Fast forward to August 2024, more than a year after Prentiss's settlement, and another attorney from Robbins Schwartz apparently offered a completely contradictory take. This new advice suggested Prentiss had indeed broken the law. Now, if you're District 86, receiving conflicting legal opinions like that, especially after already paying out a large sum based on the first opinion, has got to feel like a real punch to the gut. It's easy to see why they feel aggrieved.

The relationship between the district and the law firm clearly soured. By September 2024, Robbins Schwartz officially terminated its legal services to District 86. Their reason? They claimed the district was "unreasonably difficult" to serve. This is quite a statement, especially considering the firm was reportedly on track to earn a whopping $1 million from the district that year. Talk about a dramatic exit!

Robbins Schwartz, through its current counsel, the Wilson Elser law firm, isn't taking these accusations lying down. They've countered District 86's claims with a strong defense. Their main argument, put forth in a court brief just last month, is that the district's counterclaim falls well outside the two-year statute of limitations. In other words, they're saying District 86 waited too long to bring these specific allegations to court. They also argue that the district "fails to point to any specific excerpt of the alleged advice," suggesting the claims are vague. Plus, they assert that District 86 essentially admitted it intended to fire Prentiss regardless of the legal advice, and that Prentiss might have sued anyway if fired for cause. And those costs for interim superintendents? Robbins Schwartz contends those would have been incurred regardless of their advice, which, you know, makes a certain amount of logical sense.

District 86's attorney, Gary Grasso, however, remains confident. He's publicly stated his belief that Robbins Schwartz's statute of limitations argument is "not well-founded," suggesting there's more to this legal timeline than meets the eye. So, as you can see, this isn't just about money; it's about trust, responsibility, and who ultimately bears the cost when legal counsel goes awry, or is perceived to have gone awry. This case, pitting former allies against each other, is certainly one to watch in the Hinsdale community.