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It’s been a roller coaster of a case, starting with a 2016 indictment that shook City Hall and Mayor Martin J. Walsh’s administration. Two of Walsh’s top aides were accused in federal court of extortion, for allegedly forcing a concert promoter to hire union stagehands or risk losing lucrative permits.

In the following years, legal battles led to the indictment being dismissed — allowing the administration to breathe easier and the aides to return to work. But an appeals court then decided to put the case back before a jury.

Now, more than three years after City Hall aides Ken Brissette and Tim Sullivan were indicted, they are set for a high-profile trial next week that could close out a series of questions that has stalked the Walsh administration and leave an imprint on the former labor leader-turned-mayor’s public advocacy for unions.

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Among the questions:

What role did the mayor or other city officials have in the alleged pressuring of the concert promoter?

Was Walsh called before a grand jury (a question he has refused to answer) and will he testify at the trial?

Is it a crime for a city official to demand that independent event organizers hire union workers?

Defense lawyers argue there was nothing wrong with pushing for better pay for constituents.

“The value [of a trial] is clear: Vindication or not, there’s an end to the process and a chance for the prosecution and the defense to have this repose,” said Daniel Medwed, a law professor at Northeastern University.

A final pretrial conference — the first since the appeals court decision that resurrected the case in March — is slated for Monday, and jury selection should begin July 22.

The case involves allegations that Brissette, the city’s head of tourism and entertainment, and Sullivan, head of intergovernmental affairs, pressured Crashline Productions to hire union stagehands to organize the Boston Calling music festival on City Hall Plaza in September 2014.

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The promoter had already hosted the concert multiple times with nonunion workers. But on the eve of the 2014 concert, Crashline ultimately hired eight stagehands and one foreman from the International Alliance of Theatrical Stage Employees.

Medwed said a three-year-old case, with allegations dating back to 2014, could affect the quality of juror selections, as well as the accuracy of witnesses’ recollections.

And recent US Supreme Court decisions limiting the scope of public corruption cases could have an effect on how the case plays out, he said.

Nevertheless, he said, both sides will be looking for closure.

“Whatever view you’re willing to endorse, the end result can give us some closure, and there’s value in that,” he said. “The trial is the key moment.”

David Lurie, a Boston attorney who has followed the case, said the public deserves closure. With the charges looming, both Brissette, with a $99,900 salary, and Sullivan, who made $123,000 last year, have remained on the city payroll, and returned to work last year.

Lurie said the city has yet to fully respond to the allegations: He questions how much work was done by a committee that was supposedly set up to review the city’s permitting process.

“I’m hoping the trial will show whether they held up permits until Boston Calling agreed to hire union workers, why they did that, and whether the jury agrees the conduct was wrongful,” he said.

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On Monday, US District Judge Leo T. Sorokin will look to resolve last-minute legal arguments before trial, including the question of whether prosecutors can refer to Brissette and Sullivan individually, or more broadly as representatives of City Hall.

Prosecutors recently argued in court records that the alleged extortion victims in the case (Crashline representatives) felt pressure “based on the words and actions of the defendants, their co-conspirator, other city of Boston employees and Mayor Martin J. Walsh himself.”

In court records, the prosecutors did not identify the alleged co-conspirator.

But city e-mails previously obtained by The Boston Globe through a public records request show that the mayor’s chief of policy, Joyce Linehan, was brought into meetings between Brissette and the Crashline representatives over the hiring of union stagehands just weeks before the concert was to be held.

In one e-mail, written at the time of the alleged extortion that was outlined by prosecutors, Linehan told the festival organizers: “I hope I can deliver some good news. This conversation should have happened in May, not now.”

Linehan has refused to comment, and city officials would not comment on the case, citing the pending proceedings.

Last year, Sorokin dismissed the indictment after prosecutors acknowledged they could not prove Brissette and Sullivan had committed a crime under the judge’s narrower interpretation of federal Hobbs Act on extortion, and the way he planned to instruct jurors on the law.

Prosecutors appealed, and a federal appeals court ruled in March that Sorokin had misinterpreted the law: The court agreed that prosecutors are required only to prove that Brissette and Sullivan had an interest in having Crashline hire union workers because it would support the political ambitions of Walsh, a former head of a union trade group who was elected with the help of organized labor’s support.

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In August 2014, as negotiations were underway, Colleen Glynn, the business manager for IATSE, sent Sullivan a draft agreement for union work with Boston Calling, asking him to “Please pass it along to the production team . . . I’m confident we can get a deal for a dozen or so stagehands especially with mayor Walsh’s backing.”

In separate e-mails, after the stagehands were hired, the union signaled appreciation and support for Walsh.

Lawyers for Brissette and Sullivan have argued, however, that there is nothing wrong with city officials advocating for better pay and work benefits for constituents. They argued that the City Hall aides never threatened any harm or personally benefitted — the requirements for an extortion conviction — and say the US Supreme Court has warned prosecutors not to overreach in criminalizing the work of government officials who are simply acting in their capacity as political figures.

“Every day, political people, including in government, advocate for their citizenry and their constituents,” said Thomas Kiley, an attorney for Sullivan.

Prosecutors argue that Sullivan and Brissette went too far in demanding union workers, with the looming threat that organizers could lose their permits and the possibility of hosting concerts on City Hall Plaza in the future.

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“The conduct before this court involves public officials putting pressure on an employer, through threats of economic harm, aimed at coercing the employer into entering into an agreement to hire members of a labor union. That is extortion,” the prosecutors argued in a recent court filing.

What is clear is that the case is the first of its kind in a federal court in Massachusetts, what the appeals court called a “novel theory of Hobbs Act extortion.”


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