He won at trial but skipped one filing - it cost him more than half
A fired cop won $800,000 at trial - then lost more than half on appeal because he never updated his complaint.
The First Circuit ruled on September 21, 2026, that $500,000 in damages should not have reached the jury because the officer's original lawsuit did not cover the conduct that generated them.
Here is the backstory. The officer, a detective with the City of Somerville, Massachusetts, police department, was terminated in May 2018. An internal investigation found he kept using a confidential informant to track down a burglary suspect - even after the informant told him he planned to hurt the man. The informant found the suspect and attacked him with a machete. The officer, assigned to investigate that very attack, did not tell colleagues about his own role.
Text messages on the informant's phone gave the game away. The Middlesex County District Attorney's Office sent a Brady letter - a formal warning that the officer's credibility issues would be disclosed in any future case where he testified. The mayor fired him.
The officer fought back on two fronts. He filed a federal lawsuit alleging the real reason for his termination was retaliation - he had written to the mayor accusing the department of selective discipline. He also took the termination to arbitration under his union's collective bargaining agreement.
The arbitrator partly agreed. Three years after the firing, the arbitrator ordered reinstatement but denied back pay - suggesting the conduct warranted serious consequences, just not dismissal.
Rather than return the officer to active duty, the mayor placed him on paid leave, pointing to a second Brady letter. That decision became the problem.
The officer never amended his complaint to challenge the paid-leave decision. The jury still awarded damages for it - $200,000 in lost compensation and $300,000 in emotional distress on top of the $300,000 already awarded for the termination itself.
The First Circuit said that was a step too far. The paid-leave question was a separate factual issue the defendants never agreed to litigate, the court held. They had objected at every stage. Without an amended complaint or consent under Federal Rule of Civil Procedure 15(b), the issue should never have gone to the jury.
The $300,000 for the original termination stood. The liability findings were not disturbed.
For HR professionals managing discipline, arbitration, and reinstatement in unionized workplaces, the takeaway is practical: when an employment dispute evolves after filing, the pleadings need to keep pace. A jury verdict built on claims never formally raised may not hold up.
