Federal Court Cautions Former Bainbridge Para-Educator in $5M Lawsuit Over AI Use

A federal lawsuit against the Bainbridge Island School District has hit an early procedural roadblock. A federal judge issued a stern warning this week to the former employee representing himself: artificial intelligence is no excuse for ignoring court rules.

The legal battle arrives as the Bainbridge Island School District is already grappling with a high-profile federal civil rights lawsuit alleging administrators ignored a toxic culture of abuse.

In this second federal lawsuit, filed March 10, 2026, former para-educator Jacob Freimark is seeking roughly $5 million in damages against the district, Superintendent Amii Thompson, Special Education Director Annalisa Sanchez, and several school board members.

Freimark claims his December 2025 termination was pretextual and that he was actually fired in retaliation for speaking out as a citizen on matters of student safety and policy compliance.

The district counters that he was dismissed for performance issues, including wandering, leaving a student unsupervised, and using a personal cell phone during instructional time. Freimark actively contests these claims.

Motion Denied

On April 28, U.S. District Judge Benjamin H. Settle denied a motion by Freimark “to supplement the record and for consideration of additional evidence.”

In his order, Judge Settle chided Freimark for a series of procedural missteps, noting the plaintiff had filed “two memoranda in anticipation of and in opposition to motions to dismiss that have yet to be filed,” along with exhibits untethered to any pending motion.

“The Court does not peruse the docket looking for exhibits or briefs untethered to a pending motion,” Settle wrote, denying the request.

The reprimand follows Freimark’s April 1 memorandum formally disclosing his use of “artificial intelligence-assisted software tools” to format, organize, research, and draft “all portions” of his legal filings.

Addressing Freimark’s pro se status, Judge Settle provided a detailed explanation of the court’s expectations. “It is true that a pro se litigant is not held to the same standard as a licensed attorney,” Settle acknowledged, noting that a complaint should typically be “judged only by function, not form.”

However, Settle drew a hard line regarding motion practice. “But the rule of liberal construction does not apply to a pro se litigant’s own motions, and a pro se plaintiff is not immune from the rules of civil procedure,” the order stated.

Referencing Freimark’s technology disclosure directly, Judge Settle delivered a pointed caution: “Freimark is cautioned that his reliance on artificial intelligence does not excuse him following the rules and the Court’s Orders.”

Judge Settle clarified the appropriate venue for Freimark’s documents, stating, “He may offer evidence with a proper foundation, consistent with the Federal Rules of Evidence, at trial.”

However, the judge issued a final warning that “it is improper and unproductive to simply file exhibits and evidence on the docket... unconnected to any pending motion. Future filings of this nature may be stricken.”