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A prominent retired federal judge is criticizing a state court judge for refusing a request by prosecutors Tuesday to drop some charges filed against the Straight Pride counterprotesters, calling the move “really not in the zone of legitimate.”

“Is the judge going to prosecute the case?” Nancy Gertner, a former federal judge in Boston who now teaches at Harvard Law, said Wednesday. “These are the kinds of judgments that a prosecutor makes.”

Gertner was reacting to Boston Municipal Court Judge Richard Sinnott’s decision to deny the request from District Attorney Rachael Rollins’s office.

As members of the police union looked on Tuesday, Sinnott agreed to drop charges against just two of the 16 protesters who came before him: a 63-year-old Vermont woman charged with disorderly conduct and a 21-year-old Worcester man accused of disorderly conduct and resisting arrest.


Prosecutors asked for dismissal of nonviolent charges against seven more people, most in exchange for eight hours of community service. Sinnott denied the requests. Prosecutors did not ask Sinnott to drop any charges of assault or of violence against police.

Sinnott “can’t say ‘I don’t agree with your policy [to not prosecute certain non-violent crimes] Rachael Rollins,’ ” Gertner said. “As a judge, I oftentimes disagreed with the cases brought in front of me.” However, she said, “in a system of divided power” prosecutors make the charging calls.

And forcing prosecutors to pursue cases they don’t want isn’t tenable, according to Robert Bloom, a BC Law professor and former prosecutor. If prosecutors think a case should be dropped, Bloom said, “then who’s going to prosecute it?”

He said a prosecutor “has an ethical obligation to seek justice. If a prosecutor in the first instance doesn’t feel like charges were justified, judges usually go along with the prosecutors.”


Sinnott declined to comment through a Trial Court spokeswoman.

The Massachusetts Rules of Criminal Procedure give prosecutors “absolute” discretion to file a formal dismissal of charges, known as a nolle prosequi, which must be accompanied by a written statement from the government explaining the reasons for the decision.

The statements are often brief, citing developments such as the unavailability of a witness or the interests of justice.

“The decision to enter a nolle prosequi as to all or any distinct part of pending charges is discretionary with the prosecuting attorney,” say the rules posted to the official state website. “Power to enter a nolle prosequi is absolute in the prosecuting officer from the return of the indictment up to the beginning of trial, except possibly in instances of scandalous abuse of the authority.”

A footnote says the federal courts allow “dismissal by the prosecution only with leave of court. It did not seem advisable to engraft this additional requirement onto the Massachusetts rule, however, since it is doubted that the court has the power to compel the Commonwealth to proceed with a case which it does not believe warrants prosecution.”

Gertner said that in seeking a judge’s dismissal from the bench rather than a nolle prosequi, Rollins’s office was seeking to compel some of the defendants to perform community service. With a nolle prosequi, they’d walk out of the courthouse without any consequences.

Regardless of the rules, the clash that played out Tuesday in Sinnott’s courtroom mirrors a growing trend nationwide, according to Mark J. Geragos, a high-profile defense lawyer based in L.A. whose client roster has included Michael Jackson, Chris Brown and Winona Ryder.


“Progressive Prosecutors are often at odds with police and their unions and the clash plays out in the courtroom,” Geragos wrote, adding that the “DA’s in Philadelphia and Cook County Chicago are the most prominent” examples.

It’s a trend that US Attorney General William P. Barr lamented during an address last month at the Grand Lodge Fraternal Order of Police’s 64th National Biennial Conference.

Barr cited what he called “the emergence in some of our large cities of District Attorneys that style themselves as ‘social justice’ reformers, who spend their time undercutting the police, letting criminals off the hook, and refusing to enforce the law,” according to a transcript of his remarks. “These anti-law enforcement DAs have tended to emerge in jurisdictions where the election is largely determined by the primary.”

Rollins on Tuesday defended her office, saying in a statement that Sinnott “punished the exercise of individuals’ First Amendment right to protest” and that the allegedly violent offenders who were charged “will be held accountable for actions that put the safety of the public and law enforcement at risk.’’

Sinnott, 63, is relatively new to the bench.

Governor Charlie Baker nominated him in 2017 and said at the time that Sinnott’s “diverse legal experience and his commitment to human rights laws will make him a welcome addition to the Trial Court system.”


A lifelong Boston resident, Sinnott “practiced civil and criminal law from his own law office for more than 25 years,” Baker’s office said at the time of his nomination. “An Army Reserve judge advocate and Iraq war veteran, Sinnott also serves as an adjunct professor at Suffolk University Law School where he teaches law of war. He also teaches law and human rights to international military officers at the U.S. Department of Defense Institute of International Legal Studies. He is a graduate of Boston Latin School, Norwich University and Suffolk University Law School.”

A Baker spokeswoman didn’t immediately respond to a request for comment.

Gal Tziperman Lotan and John R. Ellement of the Globe Staff contributed to this report. Travis Andersen can be reached at travis.andersen@globe.com. Follow him on Twitter @TAGlobe.