Earlier this week, Boston Mayor Michelle Wu filed an ordinance limiting the hours when picketing is allowed outside certain homes, including her own. Adam Reilly, politics reporter and host of Talking Politics, and Erin O’Brien, UMass political science professor, joined hosts Paris Alston and Jeremy Siegel on Morning Edition to talk about free speech and harassment and more local politics news. This transcript has been edited for clarity and length.

Jeremy Siegel: Adam, Wu wants to restrict residential picketing between the hours of 9 p.m. and 9 a.m. That's a change from 7 a.m. It's a response to anti-vax protesters who have been camping outside of her Roslindale home. There's been a swift response saying that this reduces the privilege of free speech, but these are protesters banging on pans using megaphones early in the morning. What is the balance between what's been called harassment and the First Amendment here?

Adam Reilly: That's a great big and tough political philosophical question to start the day with. I think the balance depends on who you're talking with. For the mayor, as you mentioned, the protesters have been showing up and kicking things off at 7:00 a.m. at her home in Roslindale. She wants this 12-hour blackout in the evening. For the mayor, it's a balance between First Amendment rights and quality of life issues. When I talked to her about this last weekend before she filed it, she said the First Amendment guarantees you the right to assemble and make your grievances heard. It does not give you the unfettered right to say whatever you want, whenever you want, in whatever manner, to whoever you want to. I'm paraphrasing, but that was the gist of what she said.

Now for the protesters, and I think this is where it gets tricky. The protesters see themselves as fighting unconscionable tyranny. And for a lot of people who don't agree with them about the mayor's COVID mandates, that just doesn't make a lot of sense. But if the restriction is implemented on them, it will also be implemented on people who, those of us spectating may be more inclined to sympathize with. And I think that's what gets tricky here.

Paris Alston: Adam, there was a small group outside of Wu's house, they were a dedicated group. But is this a bigger problem for Wu? I mean, especially now that we see that she's taking this action to respond to it.

Reilly: You know, she said, the two people who were arrested recently trying to get into State House, not going along with their new COVID protocols, were regulars or have been regulars outside Wu's home. So there is this small band of diehards that have been finding ways to protest around the city.

That being said, I went back and watched a city council hearing on various COVID related matters that occurred last week. And in that meeting, Michael Flaherty, who ran for mayor of Boston once, he was the top vote getter in the at-large race this past fall, he was raking the Boston Public Health Commission over the coals, saying he's completely lost faith in their ability to respond to this in a thoughtful, sophisticated, methodical way. I'm not sure he's saying that because of the protests, but I think you can say that as fringy as the protests may seem on occasion, there is also a sort of more mainstream depth of frustration with some of the mayor's policies or her administration's approaches.

Alston: And Erin, the governor has also had protests outside of his house, and he's backing Wu up on this. Does that make sense to you?

Erin O'Brien: They're both public servants and they want to sleep.

Alston: But do you think it's different for Mayor Wu as a person of color, as a woman?

O'Brien: I do, actually. Mayor Wu, more seriously, has been treated abhorrently in many quarters, you know — the internet hate she takes, these aren't just protests. Often, not always, they are tinged with racism overtly and, well, very overtly and sometimes more subtly. And you know, she does have a family, she has small children and she's been treated so abhorrently. But I actually think this is one of the very few places where her being a woman, especially a mother, maybe to a lesser extent, a woman of color, that Bostonians are more sympathetic to the idea that this ban could go through.

Many, not all, Bostonians, identify as Democrats. And so you would, "hey, nothing to impede on free speech, the right to protest." And Governor Baker has had protesters outside his house for a very long time. He's also a very rich man. He doesn't have children at home. And so I don't think he has garnered quite the same degree of sympathy. But again, this is in the larger context of Michelle Wu being subjected to very racist and gendered attacks all along. But I think Boston's willingness or openness to even consider this 12-hour ban is in part because she's a mother.

"This is in the larger context of Michelle Wu being subjected to very racist and gendered attacks all along."
-Erin O'Brien

Reilly: I'd also mention, the governor has had a ton of protests outside his home, some of which can get really, really ugly. I've seen a fair amount of those, but they're not a daily event the way they have been for the mayor.

O'Brien: That's a good point.

Siegel: And we also wanted to talk about the push to tax pricey real estate sales in Boston. The Boston City Council approved Mayor Wu's proposal to create a new tax on high end real estate transactions to fund affordable housing. But now it needs to get through the State House. Yesterday, Boston Public Radio heard the governor say he's skeptical of the idea. What do you expect the legislature to do here?

O'Brien: This is the most Massachusetts of problems. Like I already said, there is a ton of Democrats in Massachusetts. We would think that a two percent tax on real estate transactions over $2 million, and it doesn't kick in until that after $2 million, for affordable housing should be a no brainer. But those of us who live here know that that's not the case.

There's real questions of home rule here, but this is really an institutional problem. I think the legislature doesn't want to cede any power to the city of Boston. The legislature understands itself as the number one game in Massachusetts and the city of Boston understands itself as the number one political game in Massachusetts. So I think what's going on here, even though it is a seemingly popular policy — yes, real estate interest groups and builders don't want it, but I think on balance, the policy itself is something that Democrats should be for. But, in the weeds sort of politics stuff, I don't think the state legislature wants to hand power over to Michelle Wu, who is already more well-known than every single individual in the state legislature.

Alston: Adam, Governor Baker on BPR yesterday said that he generally doesn't support these sorts of things, although he later went on to say that he does support these sorts of things, but this one is different. What's your read on that?

Reilly: Yeah, I'm glad you highlighted that because there does seem to be something of a contradiction there. I think he's uncomfortable with maybe not just Boston, but there's a number of municipalities that have proposed implementing tax on high end real estate sales like Boston just proposed. Perhaps some of that institutionally based. As Erin alluded to, the real estate lobby is fairly powerful. The governor may be paying attention to them.

There's also a push at the State House to make a legislative change that would just let municipalities do this without having to go hat in hand to the Legislature. It's finally worth noting — the Governor, he's going to be gone soon, and he might not be the one who has the final say as governor when this thing finally passes, if it passes the Legislature.