Middletown school district takes fight to save undefeated football team's season to court
Justice Verris Shako assigned to emergency case as hearing could come Friday, one day before championship
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Middletown’s undefeated football team didn’t give up on the field this season — and now they’re refusing to give up their fight for a championship off it.
After making history with their first undefeated regular season in 65 years, the Middies are fighting for a chance to finish what they started. Their championship dreams were shattered by an eligibility mistake made by adults, but the players are still practicing, hoping a judge will give them one more shot.
The Middletown school district filed an emergency petition Wednesday in Orange County Supreme Court asking a judge to overturn a Section IX decision that knocked the team out of Saturday’s championship game against Newburgh.
News 12 has confirmed that Justice Verris B. Shako has been assigned to the case. A hearing date and time have not yet been set, but court officials tell News 12 the case could be heard as early as Friday, November 13, just one day before the championship. News 12 is monitoring the court calendar for further developments.
“After we told those kids everything was lost, the entire season, it was a really, really rough day,” said Isaac Cayetano, an assistant coach for Middletown’s varsity football team, in a video posted to TikTok.
But instead of walking away, Cayetano says the players returned to the field within an hour, determined to keep practicing while the district fights for their chance to compete.
“They really showed up and came back like, yeah, we need a ball. We wanna practice one more time. We want to take back what was taken from us,” Cayetano said. “It was the most beautiful thing I’ve ever seen in my life.”
The controversy centers on a soccer player who joined the football team as a kickoff specialist and participated for just 53 seconds in the November 6 playoff game against Valley Central. The district acknowledges that the student did not meet a requirement to be eligible for three regular-season football contests before participating in the postseason.
But the district argues the punishment is excessive and unfair to the rest of the team.
In its initial public statement, the district identified the student’s participation in a postseason game as the eligibility issue. However, its subsequent court filing also describes the student participating in an October 30 regular-season game against Kingston.
The district says the student completed the required 10 football practices but had not satisfied the separate postseason eligibility rule.
Section IX denied the district’s request for a waiver, and the New York State Public High School Athletic Association subsequently rejected its appeal. The district is now asking a judge to intervene before Saturday’s championship, arguing that the consequences extend far beyond the football field.
“I don’t know why I should be punished for higher-ups’ mistakes,” said one senior linebacker. “I feel like as a kid, I shouldn’t be going through stuff like this.”
Other players say the season represents years of hard work, friendships and opportunities to earn college scholarships.
“Some of us are hoping to earn college scholarships. Every game is another opportunity to show what we can do,” one player said.
Could a judge overturn the disqualification?
Middletown’s legal challenge comes after other New York student-athletes successfully fought eligibility decisions in court.
In February 2025, six Northport High School wrestlers on Long Island were barred from postseason competition after their coach mistakenly allowed them to exceed the maximum number of tournaments permitted during the regular season.
Their families went to Suffolk County Supreme Court, where a judge granted emergency relief allowing the students to compete. Their attorneys argued that the athletes had done nothing wrong and would suffer irreparable harm if they were denied the opportunity to participate.
A similar dispute unfolded in November 2024, when Syracuse’s Institute of Technology football team was forced to forfeit a playoff victory over an eligibility issue involving a player who had been ejected from an earlier game.
A state Supreme Court judge overturned that decision, allowing the team to continue its playoff run. The court found significant problems with how the eligibility determination and appeal process had been handled.
Those cases demonstrate that athletic eligibility decisions can be challenged successfully in court.
But there are important differences.
In the Syracuse case, the underlying eligibility determination itself was disputed, and the judge identified procedural problems with the appeals process.
Middletown, by contrast, acknowledges that its player did not meet the three-contest postseason requirement.
That could make its case more difficult, particularly because athletic associations are responsible for enforcing eligibility rules consistently across competing schools.
The district’s argument centers on whether disqualifying an entire team over an acknowledged administrative mistake is an excessive consequence, especially when the student involved played only 53 seconds in a semifinal Middletown won 48-15. The district has offered alternative penalties, including financial sanctions, additional training for athletic staff and stronger eligibility checks.
Whether those arguments are enough to persuade a judge remains to be seen.
What’s next?
The lawsuit names Section IX, the New York State Public High School Athletic Association, Newburgh and Valley Central as respondents.
News 12 has reached out to Section IX officials for comment and clarification about the eligibility decision.
For now, Valley Central is scheduled to face Newburgh in Saturday’s Section IX Class AA championship unless a court intervenes.
With the game approaching, Middletown’s players are continuing to practice while the district waits for its opportunity to argue the case before a judge.
News 12 will continue monitoring the court proceedings and provide updates as soon as a hearing or decision is confirmed.
