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Again and again, as protesters arrested at the Straight Pride Parade in Boston came before a judge Tuesday, a Suffolk County prosecutor asked for leniency — for dismissal of the charges or release without bail.

And again and again, Boston Municipal Court Judge Richard J. Sinnott said no.

The courtroom scene represented a striking role reversal, with a prosecutor assuming the unusual stance of pushing for dismissals while the judge took it upon himself to keep the charges intact. After three dozen protesters were arrested at the weekend rally, which ended with a clash with officers in downtown Boston, it was the latest flashpoint between courts and reform-minded Suffolk District Attorney Rachael Rollins, who has come under previous criticism for declining to prosecute certain low-level cases.

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Tuesday night, Rollins defended her office and said, “The judge punished the exercise of individuals’ First Amendment right to protest.’’

Rollins said that some of the people were appropriately handled by the judge and “will be held accountable for actions that put the safety of the public and law enforcement at risk.’’

“For those people now tangled in the criminal justice system for exercising their right to free speech — many of whom had no prior criminal record — I will use the legal process to remedy the judge’s overstepping of his role,” she said in a statement.

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

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Five more people were held on bails ranging from $100 to $750. One man, 31-year-old Joshua Abrams of Stoneham, was held without bail because he faces charges in another county. He was accused of disorderly conduct and resisting arrest.

Sinnott released the other nine without bail and scheduled court dates for November.

In one sharp exchange, prosecutor Jessica Erickson asked Sinnott to dismiss disorderly conduct and resisting arrest charges against a 26-year-old Lowell man accused of forming a human chain with other protesters.

His behavior was “not appropriate,” she said, but prosecuting him would not make the community any safer.

“Not appropriate? It sounds like he picked up the wrong fork at dinner,” Sinnott replied tartly. The charges would stand.

“I think the general flavor of the room is that not even the district attorney’s office is deeply invested in these cases,” said Christopher Basso, a defense attorney who volunteered his time to represent some of the protesters.

Lawrence A. Calderone, vice president of the Boston Police Patrolmen’s Association, said he was pleased to hear Sinnott imposing bails and declining to dismiss charges as prosecutors wished.

“We think that these offenders that are here, most of them outside of the city of Boston, not residents of Boston, came here as agitators. Here for a specific reason, here to create havoc, not only for the Police Department but for the general citizenry that are around, for the visitors that are in downtown Boston trying to enjoy the last weekend of the summer,’’ Calderone said.

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He noted that previous district attorneys have also sought to dismiss disorderly conduct charges. “This DA’s office is doing the same thing, but the judge on the bench has taken a different position.”

Also Tuesday, three other people — Timothy Rego, Benjamin Boyd, and Kenneth Kraft Jr. — appeared before Judge Thomas R. Horgan, all on charges of assault and battery on a police officer. Horgan did not dismiss the charges.

He allowed their release but ordered them not to come into downtown Boston except for work.

The officer who patted Kraft down, Captain John Danilecki, was “operating with the knowledge that these groups advocate violence and armed ‘militant resistance,’ ” an officer wrote in an arrest affidavit.

As protesters made their first appearances, questions arose about police conduct as videos from the march circulated online showing officers used pepper spray on protesters.

Boston police officials said they plan to review officers’ conduct, as they routinely do whenever officers use force.

The department’s policy on the use of an incapacitating agent like pepper spray requires that officers “generally confine” its use to defend themselves or another person, or when an officer is met with active resistance.

Mayor Martin J. Walsh, in a statement on Sunday, said he takes “any accusation of police misconduct seriously.”

“I also want to be clear that sowing division between people is exactly the goal of Straight Pride organizers, and I will not stand for it,” Walsh said. “Just as the people of Boston work to make our values of love, inclusion, and acceptance known to all, our public safety officials work tirelessly to keep people safe from harm every single day of the year, and that will never change.”

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The 1-mile parade drew about 200 marchers Saturday, who were heckled by some 600 protesters from Copley Square to City Hall Plaza.

The parade, which included a Trump 2020 float, was organized by a group called Super Happy Fun America. Parade organizer Mark Sahady is part of Resist Marxism, a group founded by an alt-right leader that has a history of violence. That group had helped organize a “free speech” rally in Boston in 2017 that critics said attracted white nationalists.

After the parade ended, some protesters turned their anger toward police, accusing them of protecting the marchers.

Police on motorcycles drove up Congress Street to disperse the crowd, but protesters moved into the road to block their path. Officers moved into the crowd and grappled with protesters, in some cases using pepper spray. At least eight people could be seen being led away by police, including a woman who was limping.

Four police officers were injured.


Gal Tziperman Lotan can be reached at gal.lotan@globe.com or at 617-929-2043. John R. Ellement can be reached at ellement@
globe.com. Follow him on Twitter @JREbosglobe.