The federal indictment of a city worker, claims of union-related extortion and wire-taps. These are not the "best of times" for Mayor Walsh. Will they become the "worst of times"? Former United States Federal Judge  Nancy Gertner and Commonwealth Magazine Reporter  Jack Sullivan ( @reportah) discuss. 

Last week Ken Brissette, the city's director of tourism, sport and entertainment, was arrested on union-related extortion charges. The charges come after claims that Brissette used his position to strong-arm Boston Calling musical festival officials, demanding that the festival hire union stage employees or lose their permit to host the event. Brissette was elected under the Walsh administration, and now Walsh is under scrutiny for possible involvement in the alleged extortion. 

This is now the third time Walsh has been linked to possible wrong-doing on behalf of union interests. In 2012, Walsh was recorded by wiretap warning a developer that the firm would face issues if it didn't use union workers for a project (Walsh was a senior labor official at the time). Brissette was also implicated in the charges brought against Teamsters in the "Top Chef" ordeal of 2014, when the Boston labor union terrorized the cast and crew of the Food Network show. 

None of this looks good for Walsh, but Gertner stresses that there is a difference between advocating for unions and extortion. "Usually, extortion comes if people get money. Here what [Brissette] is doing is advocating for union intersts, no different I might add than when Mayor Menino wrote to Chick-Fil-A saying, 'We rather you not come to Boston because you're opposed to gay marriage,'" says Gertner.

Whether or not money was exchanged, this third scandal could be enough to seriously damage Walsh's record with voters.

"I think that it does go beyond Mr. Brissette," says Sullivan. "Ken Brissette does not have a union background. The union background comes from Mayor Walsh and his closest aides. So you have to wonder: If he didn't have these connections to the union, where is he getting his marching orders?"

Voters elected Walsh knowing full-well he served as a representative of the labor unions. But there is certainly a line where advocacy stops being "politics as usual," and becomes criminal.

Now, many are demanding that Walsh disclose whether or not he appeared before a grand jury as a witness in the federal government's ongoing investigation into Boston labor unions--so far, Walsh has stayed mum on the subject. "I do think he needs to say more," Gertner concedes. "But this is not an open and shut indictment, this is not an open-and-shut issue."

There is nothing that prevents a witness before a grand jury from talking about whether he appeared, or what he was asked--so, legally Walsh is under no obligation not to be more transparent about his involvement in the case. 

"I do think he should be more open," says Sullivan, "that is the problem, this is I think what he should say: Yes I did [appear], or no I didn't, and then that's all."