As a result of one of the deals, the mayor, in his official city vehicle, drove to the middleman’s home four or five times and collected $10,000 to $20,000 in cash each time, the indictment said.

The indictment also charged the mayor’s former chief of staff, Genoveva Andrade, 48, of Somerset, Mass., with extortion and theft and bribery, among other charges, for what prosecutors said was her role in the marijuana vendor scheme. They also claim that she turned over a portion of her salary to the mayor in exchange for getting and keeping her job.

In a meeting in June 2018 with one marijuana vendor, the mayor and Ms. Andrade agreed to a bribe of $125,000, which was later modified to $150,000, the indictment said.

As they walked out, Ms. Andrade asked the vendor if everything was all right, and when the vendor said it was, she said, “You’re family now.”

Ms. Andrade, who was the mayor’s chief of staff from November 2017 through December 2018, was hired at a salary of $78,780. The indictment said she kicked back about $22,800 of her salary to the mayor over eight months as well as portions of a separate $10,000 stipend she received.

Neither Mr. Correia nor Ms. Andrade or their lawyers could be reached for comment on Friday night.

Mr. Correia pleaded not guilty in court on Friday and was released on a $250,000 secured bond, according to court records. Information about Ms. Andrade’s status was not immediately available.

In a separate scheme, the mayor secured cash and a GMT-Master II Rolex watch made in Switzerland, known as a “Batman” because of its blue and black ceramic bezel, valued at up to $12,000, in exchange for helping an unidentified middleman with a commercial property, court records said.

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