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A federal judge on Wednesday tossed the criminal convictions of two City Hall aides, a legal vindication for them and a political victory for Mayor Martin J. Walsh in a case that has shadowed the administration for four years.

US District Judge Leo T. Sorokin overturned the jury verdicts from August that found former aides Ken Brissette and Tim Sullivan guilty of extorting union jobs from organizers of the Boston Calling music festival, under the threat of losing lucrative permits. The judge, who had signaled misgivings about the case long before it went to trial, instead entered verdicts of not guilty.

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“Neither Brissette nor Sullivan received a personal payoff or any other cognizable benefit in connection with the charged conduct,” the judge said Wednesday.

Brissette, 55, the city’s former head of tourism, and Sullivan, 40, the former head of intergovernmental affairs, had remained free on unsecured bond after their convictions while the judge reviewed the case. They resigned after their convictions in August but were seen in a broad swath of the Boston political community as unfairly targeted in an overzealous prosecution. They garnered support, including financial donations to pay legal bills, from friends and co-workers.

Their lawyers released a joint statement Wednesday saying, “Our clients are extremely gratified to have been acquitted.”

“Today’s ruling is consistent with our arguments that the evidence in this case did not support the charges brought against them,” the lawyers said. “Simply stated, Mr. Brissette and Mr. Sullivan did nothing that was wrongful.”

The statement added, “Today’s thoughtful, comprehensive ruling vindicates our clients, who have suffered tremendously through this long case. Mr. Brissette and Mr. Sullivan are looking forward to moving on with their lives.”

Federal prosecutors could still appeal Sorokin’s change of the verdict. In a statement late Wednesday, US Attorney Andrew E. Lelling said, “An impartial jury, following legal instructions written by the court, voted unanimously to convict these two men. We are disappointed by this decision and will review our options.”

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The jury of eight women and four men had reached their verdict after only six hours of deliberation, following a two-week trial.

But even if prosecutors successfully appeal Sorokin’s decision to vacate the verdicts, the judge preemptively said Wednesday that he would order a new trial for Brissette and Sullivan. That raised another bar for prosecutors to meet to secure a conviction in a controversial case that, defense attorneys argued, has had a chilling effect on the everyday give-and-take politics of City Hall.

It is rare for a federal judge to overturn a jury verdict.

“This action is required based on the government’s failure to prove that either man committed the charged offenses,” Sorokin said in his ruling, acknowledging his “unusual” action to overturn a jury verdict. The judge found that prosecutors were looking to apply the federal Hobbs Act extortion law to conduct that is typically governed at the state and local level, and may not be considered criminal.

“Even under the government’s narrower view of its burden of proof, it failed to establish that either defendant acted wrongfully, as is required to sustain an extortion conviction,” the judge said, adding, the government also "failed to prove that either defendant, in fact, knowingly violated either state ethics law or local policy.”

A spokeswoman for Walsh, a former labor leader whose relationships with local unions were under scrutiny during the trial, said the administration was reviewing the decision. Walsh will face voters next year if he runs for reelection, so the overturned verdict potentially removes a political headache for the mayor.

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The case was originally filed in 2016 as part of a broader federal review of alleged union strong-arm tactics in greater Boston, and it followed the unsuccessful prosecutions of Teamsters members accused of shaking down jobs from producers of the popular “Top Chef” television show. Brissette had been accused of using the weight of City Hall influence to advocate for the Teamsters.

Later, he and Sullivan, also a former labor leader, were accused of pressuring producers for the Boston Calling promotional company, Crash Line, to hire union stagehands who had supported the mayor’s 2013 election campaign, or lose out on lucrative permits to run their concert on City Hall plaza.

Lawyers for Sullivan and Brissette argued that they were simply looking to negotiate a deal to avoid an embarrassing picket, with an oversized inflatable rat, that had been threatened on the plaza. They accused prosecutors of overreaching.

The case took years to get to trial. Sorokin initially dismissed the indictment in 2018, after prosecutors said they could not proceed under the standards the judge set out for the trial. Then, in early 2019, an appeals court in Boston overturned Sorokin’s decision, specifically his outline for jurors to interpret the law, and the case was reinstated.

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Sorokin did not hide his misgivings about the case, even after the appeals court ruling: At one point at the close of the trial, he had claimed, “I think there are issues of [criminal] intent,” a benchmark for a prosecution.

In a 90-page decision Wednesday, Sorokin based his ruling on three technical legal arguments.

Prosecutors, he said, were required to prove the existence of a quid pro quo, or the exchange of a personal payoff for Brissette and Sullivan, because both defendants were acting in their capacities as public officials. But, he argued, prosecutors failed that burden.

Moreover, the judge said, prosecutors failed to show that the defendants did anything legally wrong in furtherance of an extortion conspiracy, saying prosecutors cannot criminalize labor contract negotiations.

And, the judge found, prosecutors failed to prove beyond a reasonable doubt that Brissette and Sullivan knew about and intended to exploit Crash Line’s fears that it could lose out on lucrative permits if it did not abide by the demand to hire more union stagehands. Crash Line producers had testified only that they felt the pressure of the permit deadline, the judge said.

“Proof that a public official meets in his government office with someone seeking a permit as the end of the permitting process approaches cannot — without more, and there was no more here — establish the requisite intent for Hobbs Act extortion,” the judge said.

It is not unheard of for a judge to dismiss a case after a jury had rendered a guilty verdict. Last year, US District Judge Richard G. Stearns threw out the convictions of two people entangled in the New England Compounding Center case involving tainted pharmaceutical drugs, after they had been convicted by a jury in December 2018. Prosecutors appealed that decision.

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In 2003, US District Judge Douglas P. Woodlock overturned the convictions of two people for violating US export laws after reviewing their trial for more than eight years. He found that the export laws were “unconstitutionally vague.” The appeals court ultimately overturned his decision, however, and both defendants were sentenced in 2005, 10 years after the jury verdicts.


Milton J. Valencia can be reached at milton.valencia@globe.com. Follow him on Twitter @miltonvalencia.