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Lisa Lamberti Menino was outside City Hall, looking in on preparations for the Boston Calling festival slated for September 2014, when she saw Brian Appel, one of the concert organizers.

Appel, co-founder of Crash Line Productions, had just left a meeting with City Hall aides.

“He seemed to be very agitated, angry and upset,” Menino, Appel’s friend and an administrative assistant in the city’s property management department, testified Monday in US Boston District Court.

He told her that Kenneth Brissette, the city’s new chief of tourism, and Tim Sullivan, head of intergovernmental affairs, told him that Crash Line had to use union labor for the upcoming music festival, which was expected to bring tens of thousands of people to City Hall Plaza.

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“If he didn’t hire them, he wouldn’t get his entertainment license” for the festival, Menino said. “I couldn’t believe what I was hearing.”

Menino, the daughter-in-law of the late Boston mayor Thomas M. Menino, was one of four witnesses prosecutors put forward Monday in the extortion trial of Brissette, 54, and Sullivan, 39.

Federal prosecutors say the men exploited the festival organizers’ fear that the concert and perhaps their entire business would be ruined if they didn’t hire union workers. Prosecutors say they were motivated to secure the jobs to please Mayor Martin J. Walsh, a former union leader who was elected in 2013 with the widespread support of organized labor.

Defense lawyers have countered that Sullivan and Brissette asked, but did not demand, that Crash Line hire members of International Alliance of Theatrical Stage Employees Local 11 to avoid the embarrassment of a union picket.

They have also argued through prosecution witnesses that delays in approving the festival permits stemmed from the Boston police, who were looking to place restrictions on its liquor license.

Menino testified that Sullivan and Brissette had the power to withhold permits for the festival but acknowledged on cross-examination that the City Hall official responsible for its entertainment license was Patricia Malone, then the commissioner of consumer affairs and licensing, who communicated often with the police.

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“She had complete authority over the entertainment license that would be issued by the city,” said William Kettlewell, Brissette’s lawyer.

“Yes,” Menino replied.

“You knew that whoever was sitting in the Office of Tourism and Special Events didn’t control what Mrs. Malone did,” Kettlewell said.

“Yes,” Menino said.

Other City Hall employees are expected to testify this week, including Joyce Linehan, Walsh’s policy chief who dealt directly with Crash Line in 2014.

On Monday, the jury heard testimony from Steve Oare, who had a private meeting with Brissette in 2014 when he was seeking permits to film a commercial for “Top Chef,” a television reality show.

Two years ago, four Teamsters were acquitted on extortion-related charges after they were accused of bullying “Top Chef” producers who had refused to hire them for filming. Prosecutors have relied on witnesses from that trial to show that Brissette was allegedly pressuring people to hire union workers as a condition of permits. Brissette has not been charged in connection with the “Top Chef” case, which resulted in the conviction of one Teamster, Mark Harrington, who pleaded guilty to attempted extortion.

Oare said he had already planned to hire Teamsters for his commercial shoot at Sportello restaurant when Brissette asked him if he would be using union labor. Assistant US Attorney Laura Kaplan asked Oare what he believed Brissette meant by that.

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“That we needed union labor to receive the permits,” Oare said.

During cross-examination, Kettlewell brought up the well-publicized tensions between the Teamsters and “Top Chef” that led to a clash outside a Milton restaurant where the show was filming.

“You were aware that when Top Chef had filmed in Boston that the Teamsters had posed a problem for them,” Kettlewell said.

“I had read about it, yes,” Oare said.

The day closed with brief testimony from Colleen Glynn, the business manager for IATSE Local 11. Assistant US Attorney Kristina Barclay asked Glynn how she knew Sullivan, a former political director for the Massachusetts AFL-CIO. Glynn mentioned that she had taken a union course taught by Sullivan.

“I think the name of it was ‘Labor and Political Power,’” she said.


Maria Cramer can be reached at mcramer@globe.com. Follow her on Twitter @globemcramer.