A case is dismissed, and the cloud that loomed over Walsh dissolves

Timothy Sullivan (left) and Kenneth BrissettePAT GREENHOUSE/GLOBE STAFF/FILE

It was an explosive case, a public corruption probe with the potential to undermine a new mayor’s political agenda.

In 2014, Boston Mayor Martin J. Walsh’s administration came under FBI scrutiny for its cozy relationship with organized labor. Two years later, a pair of high-ranking City Hall officials were indicted on charges they threatened to withhold permits from organizers of the Boston Calling music festival unless they hired union members, a violation of the federal law prohibiting extortion. There was speculation more indictments would follow, casting scrutiny on a mayor with deep ties to organized labor.

That case collapsed Thursday, when US District Judge Leo T. Sorokin dismissed the charges against Kenneth Brissette and Timothy Sullivan after prosecutors conceded they could not secure a conviction under his interpretation of the law. Prosecutors say they will appeal, a process that could take at least a year.

“I appreciate this being brought to resolution,’’ Walsh said in a statement. “I look forward to continuing our focus on moving the city forward and working to expand opportunities for Boston residents, every day.”

Legal observers are divided on what led to the case’s demise. Some said prosecutors overreached from the start, others pointed to a 2017 Appeals Court ruling that made it harder to prosecute union officials charged with extortion under what is known as the Hobbs Act.

“The die [was] already cast,” said Wally Zimolong, a Philadelphia-based attorney for construction companies who has followed union extortion cases around the country. “The battle was lost when they lost in the First Circuit.”

Last September, the First Circuit Court ruled that two Teamsters from Massachusetts, John Perry and Joseph Burhoe, could not be convicted of extortion under the Hobbs Act.

The court said the defendants were seeking to land real jobs — and not just extract money — from an employer when they threatened to picket businesses if they did not hire union workers.

The decision forced Massachusetts prosecutors to change their legal strategy. Prosecutors who had initially argued that Brissette and Sullivan were acting as agents of the union revised their theory to say the men had violated federal laws when they allegedly forced Boston Calling organizers to hire people they did not want.

Zimolong said the dismissal of the case is a troubling sign for businesses. In cities such as Buffalo and Philadelphia, traditionally powerful unions that have lost clout in recent years have been strong-arming private companies into hiring them, a tactic that led to an increase in federal prosecutions, Zimolong said.

“Unions have acted very aggressively to protect their traditional market,” he said. “State prosecutors either don’t have the stomach for it or aren’t empowered to prosecute these kinds of crimes.”

But others said the Burhoe decision only provides more evidence that prosecutors have been too zealous in pursuing cases against unions. Last August, four other Teamsters were acquitted of conspiracy to commit racketeering, charges prosecutors filed when they said the union members tried to extort jobs out of “Top Chef,” a reality television cooking show that filmed in and around Boston in 2014.

“What’s endemic in this prosecutor’s office is this idea that extortion and fraud are open-ended vehicles for federal prosecutors to criminalize any behavior they think is improper,” said Michael Anderson, a Boston-based labor lawyer. “If the extortion statute is as broad as what the prosecution is arguing, then the prosecution has carte blanche to indict anyone whose social policy they disagree with.”

In the City Hall case, Sorokin had planned to tell members of a prospective jury that to reach a guilty verdict they would need to find that Brissette and Sullivan personally benefited when the union got the jobs at the music festival in September 2014.

Prosecutors asked for reconsideration, but Sorokin denied their motion in a 28-page ruling that implied prosecutors were looking too broadly at the law.

“The government . . . would extend federal criminal liability for Hobbs Act extortion to any scenario in which a public official acting as a regulator requires a private entity to hire . . . people or to otherwise spend money in a specified way,” Sorokin wrote.

Sorokin pointed to a Supreme Court case in 2006 that stemmed from a law signed by Massachusetts Governor Mitt Romney requiring operators of oil barges to use local pilots when guiding their vessels into local waters.

“The government has unequivocally taken the position . . . that if state officials enforced a requirement that all oil tankers in Massachusetts waters hire Massachusetts-licensed pilots . . . then these officials would have obtained the wages paid to the pilots and in so doing committed Hobbs Act extortion,” Sorokin wrote.

Sorokin’s judgment on the law is sound, said Thomas J. Iovieno, a defense lawyer who represented James Deamicis, a Massachusetts Teamster who served a year in prison for conspiring to shake down business in the Burhoe case.

Deamicis’s conviction was reversed by the Appeals Court on Tuesday.

“The Hobbs act says you can exert economic pressure,” Iovieno said. “The law says [city officials] can do that as long as they’re not personally getting a payoff.”

There were alternatives to seeking harsh federal sentences against Brissette and Sullivan, Anderson said. Crash Line Productions, organizers of Boston Calling, had the option to file an injunction against the city in federal civil court to prevent what they considered heavy-handed pressure to hire union workers they did not want, he said.

But David Lurie, a Boston litigation attorney who specializes in land use disputes, said civil action can take months and even years to resolve.

“It’s unclear what practical remedy Boston Calling would have had to force the city to follow the law and grant its permit in time for the concert to be held,” Lurie said.

Zimolong, the construction attorney in Philadelphia, said for a company facing a tight deadline to get a permit, accepting the city’s terms, no matter how unappealing, can feel like the only option.

“It’s sort of saying to the bank teller, ‘You gave up the money, it wasn’t robbery.’ Well, the guy had a gun in my face,” he said.

Assistant US Attorneys Laura Kaplan and Kristina Barclay have said they plan to appeal the dismissal based on Sorokin’s interpretation of the Hobbs Act.

They will seek permission from the US solicitor general to appeal the dismissal.

If that permission is granted, it could take at least a year before oral arguments are heard in court and just as long before a decision comes down. The Appeals Court spent more than a year deciding Burhoe.

Meanwhile, Brissette and Sullivan, who have been on paid leave since they were indicted almost two years ago, are expected to return to work now that the charges have been dismissed, city officials said. It is not clear when Brissette, the city’s tourism chief, and Sullivan, head of intergovernmental affairs, will be back.

From a political standpoint, the dismissal is a victory for Walsh, said Peter Ubertaccio, a Stonehill College political science professor.

He avoids a trial that could have embarrassed his administration, but he still faces questions about tactics his employees used to help a favored constituent, he said.

But, Ubertaccio noted, the decision reinforces earlier messages from the Walsh administration “that these guys had done nothing wrong. The distraction is gone.”