When Emotion Replaces Judgment, Taxpayers Pay

On July 31, 2025, the Superior Court held a hearing on my motion to disqualify Corporation Counsel Steven Bolton and Deputy Corporation Counsel Celia Leonard from my cases. The issue was not about winning a motion; it was whether two city lawyers, locked in years of conflict with a citizen critic, could still do the job “with the detachment that we all have to have.”

The judge made no secret of what he was probing.  He noted “PCC complaints flowing” and “federal complaints flowing,” even musing why these attorneys were “gluttons for punishment.” He stressed he was “not making any findings”, a credibility probe, not a merits ruling.

Attorney Leonard’s own words confirmed the Court’s concern. Asked about a particularly sharp objection, she answered plainly: “That particular objection was emotional, mainly because I was feeling like we are going into federal trial… There’s reputation there.” She then pivoted to the standard assurance: “Yes, I can do this job… without that emotion coming in.” Those two sentences tell the story, which is an admission of emotion, followed by promise of control. 

Attorney Bolton, for his part, gave a measured but revealing answer. He said that “almost daily, I examine my own conscience, my own motivations,” that he and Leonard have discussed it with the mayor, and that “at appropriate times, we have hired outside counsel”..., “when we feel we cannot represent the City in those cases.” He also told the Court, “We have to do it in writing,” citing “professional conduct complaints” where I supposedly attributed statements to him that he denies. And in a candid moment, he added, “I’ve thought about how long I’ll continue to do this.” These are not the words of indifference; they are the language of strain. 

The Court ultimately denied my disqualification motion that day. But the transcript reflects what the ruling could not: genuine judicial concern about emotional investment and the ability to stay detached. The judge explicitly framed the issue as whether these lawyers could still approach my matters with professional distance. That concern did not emerge from nowhere; it came from what he saw and heard. 

Context matters. Five months earlier, on February 14, 2025, a federal judge denied Attorneys Bolton and Leonard’s motion for summary judgment on my First Amendment retaliatory arrest claim. The federal court held that a jury could find that these attorneys “caused [my] arrest in retaliation” for protected speech, and that their motion “is denied.” The court also explained that, although a state judge had found probable cause and I later pled to a violation-level offense, probable cause is “not fatal” to a retaliatory arrest claim where there is objective evidence of selective enforcement (the “Nieves” exception). 

The federal court went further. Construing the record in my favor (as Rule 56 requires), it found evidence that Attorney Bolton “advocated for [my] arrest to multiple high-ranking officers,” and that Attorney Leonard later “expressed her desire to press charges,” discussed my public criticism, (an email titled “Attorney Leonard Should be Fired) and that “had the Attorney Defendants not engaged in these actions, Nashua PD would have adhered to its policy not to make trespassing arrests when the trespassing individual leaves after being asked to do so.” A jury, the court concluded, could find their conduct a “but-for” cause of my arrest. That is not my interpretation; those are the court’s words. 

Another defense the attorneys raised, “she wasn’t chilled”, met the law, not bravado. The federal court reminded them that “actual deterrence need not be shown,” and noted they even conceded my arrest was an “adverse action.” That matters because it centers the case where it belongs: on government retaliation, not on whether a critic keeps speaking anyway. 

When you place the state-court transcript and the federal order side by side, the pattern is clear: emotion → advocacy → arrest → jury question. In state court, Attorney Leonard acknowledged an “emotional” reaction linked to reputational stakes in the federal trial; Attorney Bolton described daily “examin[ation]” of conscience, consultations with the mayor, written-only communications, outside-counsel triage, and even thoughts about “how long” to keep doing the job. In federal court, the record, viewed objectively, was strong enough to send the retaliatory arrest claim to a jury. 

It is my opinion that the state judge, aware of the looming federal jury trial, chose not to make findings that could be read as pre-judging the federal issues. He said as much: “I’m certainly not making any findings.” But he asked the right question: can these attorneys still act with the professional detachment the profession requires?

Government lawyers are fiduciaries of public trust. When judgment gives way to emotion, the cost is paid not just in dollars but in rights. My case will let a jury decide whether two city attorneys crossed the constitutional line from advocacy into retaliation. Until then, the record already shows enough to warrant concern: a court probing “detachment,” an admitted “emotional” objection, a daily struggle to keep personal stresses out of public lawyering, and a federal order sending the core claim to trial. That’s not politics. That’s the public’s business. 

City Attorneys can afford emotion, but you can’t….because you are the one paying for it.