When City Attorneys Are Too Emotionally Invested, Taxpayers Bear the Liability

On July 31, 2025, I appeared before a new judge in Superior Court South for a hearing on a motion to disqualify Attorneys Bolton and Leonard from my cases. I filed that motion because both attorneys have repeatedly shown an inability to remain professionally detached, as officers of the court are required to do.

Over the past four years, I have documented nearly ten instances where the Nashua legal office or city departments unjustifiably threatened me with arrest, attempted to have me arrested, or succeeded in doing so. At the hearing, I presented emails, police reports, and other evidence of these incidents as offers of proof. The City rejected my exhibits outright, but the record is clear: Attorneys Bolton and Leonard have pursued me with a level of personal animus inconsistent with their professional obligations.

What was most striking during the hearing was not the evidence itself, but the attorneys’ reactions. Attorney Barnes, who sat first chair for the City, was repeatedly interrupted, second-guessed, and undermined by both Bolton and Leonard, who could not contain themselves. They fidgeted, whispered, tugged at his sleeve, and frequently rose to interject. It was clear they did not trust their own colleague to handle the case.

The turning point came when I referenced my 2021 arrest at City Hall. I explained, citing police reports, that after I wrote a critical letter (“Attorney Leonard Should Be Fired”), Attorney Leonard initiated a police investigation that ultimately led to an arrest attempt even though I had peacefully complied with a trespass order. Police initially refused to arrest me, noting that I had left City Hall without incident; I complied with policy. The reports confirm I was not threatening, aggressive, or disruptive. Yet a month later, after Attorneys Bolton and Leonard strong-armed top brass, the police issued an arrest warrant charging me with the maximum penalty for a misdemeanor A: up to one year in jail and a $2,500 fine.

When I recounted these facts, Attorney Leonard reacted with visible agitation. She jumped up, objecting so vocally it bordered on a scream—not on proper legal grounds, but by accusing me of lying. Such behavior is not a valid objection; it was a raw, emotional outburst.

The Court itself recognized her emotionalism. The judge specifically asked Attorney Leonard to explain her “heartfelt” reaction and whether it was “personal or just business.” Leonard admitted she was emotional, citing the pending federal trial on related issues. But that explanation fell flat. The federal trial had no bearing on the Superior Court hearing. If she believed her federal case was at risk, she could have asked her federal counsel to attend, just as my attorney did. Instead, she lashed out.

Afterward, Leonard compounded the problem by making false statements, that I had personally treated her poorly, calling her horrendous names, denied her a chance to defend herself, and named her as a defendant in multiple Right-to-Know lawsuits. None of this was supported by the record, nor by her responses to my subsequent Right-to-Know requests. False statements to the Court, especially when fueled by emotion, only reinforce the concern that she cannot remain impartial.

The Court denied my motion to disqualify but acknowledged that additional issues may be raised. While I respect the Court’s ruling, I believe it underestimated the extent to which Leonard’s personal animus compromises her professional judgment. On July 31, her emotional investment was visible to all in the courtroom, and it has been equally visible outside the courtroom for years.

Attorneys are expected to be advocates, not avengers. When they become emotionally entangled, they stop advocating and start retaliating. And when retaliation replaces reason, taxpayers bear the liability. My experience illustrates how quickly an attorney’s personal resentment can bleed into their professional conduct, leaving citizens like me exposed not to fair advocacy, but to vindictive misuse of government authority.

The law doesn’t bend to protect fragile feelings. In fact, the U.S. Supreme Court made this clear in New York Times v. Sullivan (1964): public officials and public servants are not shielded from sharp, unpleasant, even caustic criticism. That decision cemented the principle that free speech must protect the critic, not the comfort of those in power.

A federal judge has now ordered a trial on whether Attorneys Leonard and Bolton engaged in a retaliatory arrest after I exercised my First Amendment right to write a critical letter. That trial will determine whether their personal resentment crossed the line into constitutional violation. But one lesson is already clear: when city attorneys are too emotionally invested, they don’t just fail in their duties, they create liability for the very taxpayers they are sworn to serve.