Incorruptible Mass

Our goal is to help people transform state politics. We investigate why it’s so broken, imagine what we could have here in Massachusetts if we fixed it, and report on how you can get involved. If you believe in fighting for social justice, in reducing inequality, in health care for all, in affordable housing, in reforming our criminal justice system, and if you want to be part of getting these policies – and more – passed, then this is the podcast for you.

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Incorruptible Mass

State House Documentary

July 01, 2026 • Anna Callahan • Season 6 • Episode 32

0:00 | 30:32

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This week, one of the people who worked behind the scenes to make this podcast happen steps in front of the mic to discuss our State House. We'll have a discussion with filmmaker (and former Incorruptible Mass video editor) Aaron Singer about his forthcoming documentary on the State House, what it's taught him about how politics work in Massachusetts, and what we can do with that knowledge to make our state a better place for everyone who lives here.

You’re listening to Incorruptible Mass. Our goal is to help people transform state politics: we investigate why it’s so broken, imagine what we could have here in MA if we fixed it, and report on how you can get involved.

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Anna Callahan

00:00:02 - 00:01:05

Hello and welcome to Incorruptible Mass. Our mission here is to help us all transform state politics because we know that we could have a state legislature that truly represented the needs of the 7 million of us who live here. Today, we have an exciting conversation with someone who is creating a documentary on the statehouse and its dysfunction. We are going to be talking to him about what's in the documentary, all the things he has discovered, you know, things that you've heard here, but now you're going to hear them, hear his stories as well about those. So some issues and topics will come up. We're also going to hear about what stage this documentary is in, how you can help, how you can also be in touch. And we're basically going to be focusing on someone who is focusing on the issues that we care about the most. So we're very, very excited about this. Before we do, I am going to have my illustrious co-host introduce himself. Jonathan, go ahead.

Jonathan Cohn

00:01:05 - 00:01:14

Hello, I'm Jonathan Cohen, he/him/his, joining from the South End in Boston, and I've been active with various progressive issue and electoral campaigns here in Massachusetts for over a decade.

Anna Callahan

00:01:15 - 00:02:04

And I am Anna Callahan, she/her, coming at you from Medford, where I'm a city councilor, and I have spent years and years studying dysfunction and corruption and all of that stuff in politics. And so to talk to someone else who is also realizing and trying to get the word out about this is fantastic, very exciting. And now I'm going to have our special guest introduce himself. Before he introduces himself, I have to introduce that for quite a while, he did our video production, which was absolutely incredible. So he is part of our team. We feel like he's part of our family. This is Aaron Singer. And Aaron, we would love to hear a little bit about you and how you got interested in this work.

Aaron Singer

00:02:06 - 00:03:02

Yeah, I'm sure. Yeah. So my original career was working motion graphics in Los Angeles for TV. I left that career to become a teacher, came back, picked up filmmaking again, and started working on this. That's pretty much it. I, you know, I'd always been into politics for a while. I just ended it at you knock on doors for a few candidates every couple of years or the fair share campaign. When I started with this project, it was originally about daylight savings time. I wanted to do a film about why popular bills don't pass. To me, daylight savings time is— there's no reason it shouldn't pass. There's no reason we shouldn't get rid of it.

Anna Callahan

00:03:03 - 00:03:07

I agree, man. I always think anybody who ran for president on that one issue would win.

Jonathan Cohn

00:03:08 - 00:03:20

Actually, the funny thing is it's one of the rare things where I actually genuinely don't have a strong opinion on, and it's almost refreshing for me as somebody with deeply held positions on so many things to have something where I actually just don't. But continue.

Aaron Singer

00:03:20 - 00:03:31

Well, I mean, it's funny because I've realized that it seems to be one way or the other. Either people feel very strongly like me or John, like you, or they're just like, whatever, I don't care. Yeah.

Jonathan Cohn

00:03:33 - 00:03:36

There's no modestly held. No.

Aaron Singer

00:03:38 - 00:04:20

I started it going through the Massachusetts legislature website and realizing very quickly, oh my gosh, I can't really follow what's going on. I can't track these bills. I saw that the Senate had done a study recommending us get rid of Daylight Savings Time in 2017. And then I kept looking at it more and it looked like they did two more studies after it. And that's when I learned that studies don't usually mean that they're actually studying it. And that's when I realized, oh, this is like way worse than I thought.

Anna Callahan

00:04:20 - 00:04:34

It's funny because we think of sent to study, we always tell people sent to study just means it's killed. But it often, there actually is a study made. It's not just killed before the study. It's like they send it to study and they do studies, but then nothing ever happens.

Aaron Singer

00:04:34 - 00:04:34

Yeah.

Jonathan Cohn

00:04:35 - 00:05:23

Well, I think it's also the case that if they actually want to study something, they create a commission. Right. Also always the big divide that if they're actually affirmatively interested in it. Yeah, I always find it fascinating, even like the terminology, which I think is often a way of— so I feel like so much of terminology around the statehouse is designed to confuse people about what is actually happening. Because granted, this is not— this is also parliamentary jargon. I feel like if you talk about tabling something, that is how we understand in the US context, we're like, we're setting this aside, we're not touching this again. And that's what it means. To send something to study. But they like making it sound like they're actually doing work, that they actually might still do work on it. No.

Anna Callahan

00:05:23 - 00:05:34

Yeah. So Aaron, here you are. You got a film background. You're interested in politics. You're like, I wonder why a popular bill like this might not pass. Let's look into it. And then?

Aaron Singer

00:05:36 - 00:06:33

Yeah. I'm trying to think what happened first. I probably either John, you were one of the earlier people I talked to about this, or Scotya Hiller of Act on Mass, who is doing such a great job at calling attention to all of this stuff, really put on the map for me. Their website, Act on Mass's website, their newsletter has such fantastic information. That's when I really started digging in and realizing government is not what I thought it was. It does not operate anything like I thought it did. And that's kind of where it started. And then over the past year, it's been this process of learning more and more, connecting with more people who have been screwed over by the system in some way or another. And that's kind of where we're at.

Anna Callahan

00:06:34 - 00:07:08

Well, before we dive into some of the stories, which I know we're very excited to hear, like as you've interviewed people, what things you've heard, I really want to understand a little better what does it look like to create a documentary film? How long does it take? How much funding does it take? Where are you in the process? Help us and our listeners to understand because I'm sure our listeners are like, "Oh my God, there's a movie. When is it coming out?" Where are you in the process? When will it be done? How much money do you need in order to make it happen? Have you raised already? Tell us, how does it work?

Aaron Singer

00:07:08 - 00:08:20

Sure. Yeah, I mean, like the filmmaking process, there's no— the thing is like there's no rules, right? So it's basically whatever happens goes. So like there are some documentaries that have taken like 8 years to get done because people just can't get any funding at all. Some people are very good funders. They can get their funding for their film and then nothing comes out of it. Oh, dear. Yeah, so there's like a huge range. With me, Yeah, I'm, you know, my background is not in fundraising. My background is in making motion graphics and editing and writing. And so I don't, I'm not really good at the reaching out to people and calling people up for money, but I'm learning now, I guess. So what I've kind of ended up doing is launching a Substack to basically put out the information that I've been learning over the past year or so and fundraise that way, basically. So that's kind of a newer thing, but that's basically it.

Anna Callahan

00:08:21 - 00:08:35

Great. And you've got some footage. Do you have any idea of like a timeline of, you know, are you hoping that in a year or so you'll have all the footage you need to be editing? Like, because there's a whole editing process after you I don't know, you tell us.

Aaron Singer

00:08:36 - 00:09:21

Yeah. It's basically whatever I want to do, whatever I'm trying to figure out is pretty much it. In terms of when it's going to be done, less than a year. It really depends on when I could pay my camera guy. Once the footage is shot, it's a matter of just paying my rent and then sitting in my basement and editing it all together and making it look nice and stuff. That's the easy part. The hard part is figuring out what are the stories, what's the writing that goes with it, and then cutting down the huge amount of stories that I have. So figuring that out.

Jonathan Cohn

00:09:22 - 00:09:49

And that's such impressive work. I'm always impressed with documentary editing because you get, if you're interviewing so many people, you have this treasure trove of footage. And then it's like, well, nobody's actually going to sit and watch 30 hours' interactive interviews no matter how interesting they are. So then how do you take that and get it into kind of, let's say, max 2 hours coherent narrative, which is fascinating work.

Aaron Singer

00:09:50 - 00:10:30

Yeah. So usually I have— there's usually a few things that I want to hit first, right? So one of the storylines of the film is the 2006 ballot question or failed ballot question. We were supposed to— and supposed to is a— well, either way, they got enough signatures to put affordable healthcare as a constitutional right on the ballot and the legislature pulled a trick to get that off the ballot.

Anna Callahan

00:10:34 - 00:10:38

Yeah. This is one of my favorite stories. I hate this story so much.

Aaron Singer

00:10:38 - 00:12:00

Yeah. And I lived here. I had no idea that this happened. I had no idea that we could have had affordable healthcare. And so the more I've dug into that, the more I've It ends up opening up so many more places. But I know that, "Hey, that's a storyline I want to do." I start with that and then another storyline I'd like to do. Diana Desaglio, who's not exactly a progressive, but her story really helps explain the dysfunction at the State House. Going from being a staffer who had to sign an NDA to get her last paycheck, to where she's at now, where she's one of the leaders of the fight to open up the State House. I start with those points. I start with, "Hey, I know I really like these storylines," and then I kind of just work around there. Then sometimes, like last year, at the Democratic State Convention. I was not planning on covering that, but what happened at the convention was so crazy and weird, it's now going to be in the film.

Anna Callahan

00:12:01 - 00:12:02

Give us a teaser, man.

Aaron Singer

00:12:03 - 00:12:17

Yeah. So, yeah, basically what happened was we had this very progressive platform that Jonathan, you had a part in in putting together for 2001, I think.

Anna Callahan

00:12:17 - 00:12:18

No surprise.

Aaron Singer

00:12:18 - 00:12:59

Yep. And then in 2025, they had a committee that wanted to take out all of the specific language and make it really kind of as boring and dry as possible is what it seemed like to me. And then at the convention itself, It sure seemed like they were going to ram it through without— against the will of people there. So I don't know. That's kind of what we're working with for there. And yeah.

Anna Callahan

00:12:59 - 00:12:59

So what is this?

Jonathan Cohn

00:12:59 - 00:13:20

So as you were putting this together, the one thing when we were chatting before I noted this is when you go into a documentary like this, you're clearly thinking ahead of time that there's a problem here. Right, which is why you're investigating in the first place. Were there any moments where that just really hit you of like, oh, this is so much worse than I thought it was going into this?

Aaron Singer

00:13:21 - 00:14:43

Yeah, I think the most depressing part for me was meeting progressive reps who, you know, I think the world of and I think are great. And then learning they can't do what I would like them to do or else their jobs would be miserable. It's not easy being a progressive rep in the Massachusetts House. If you push too hard, if you go against the speaker too much, none of your colleagues are going to work with you. And that's what your whole job is based on. I think that was really difficult for me to really just not be okay with because I'm not okay with, but just to really accept that that's how it works. And then figuring out, okay, well, if that's the reality of how things work, What's the solution to it? And we don't have those yet. So I'm still kind of figuring that out, talking with anthropologists and all these other people that have been helping me with research. But yeah, that was not fun.

Jonathan Cohn

00:14:45 - 00:15:06

I mean, you noted that, like, I think you say talking with anthropologists, what have you learned from— like, I'm sure that obviously there are probably hours of discussion there, but like, what are the top lines that you've been learning from them about just even how power, like, power works or systems work or the many other things that people might be analyzing about a legislature?

Aaron Singer

00:15:07 - 00:16:08

Yeah, I mean, it's pretty similar to Massachusetts in a lot of ways. So a lot of them, they rely on a lack of transparency. And when people don't know what's going on, it becomes so much easier for just a few people at the top to kind of control everything. Part of it is also lack of interest from people, but part of it is just the press doesn't print what they should. Here in Massachusetts, I think last year it was 92% of Democrats in the House voted with Speaker Mariano for the entire year on every vote. I think that's crazy. Can you really imagine someone like Speaker Mariano having the same opinion on every bill of 92% of the reps in the state?

Jonathan Cohn

00:16:10 - 00:16:37

And the thing that really that's kind of striking about that is it shows you about how many things never even get there in the first place. Because if you're reaching the point of where everybody agrees on everything and we No, they'll admit that if you ask them if they don't agree with their colleagues on everything, then that's showing you how much just gets excluded from the discussion entirely about— yeah, and how many things are blocked from ever getting their fair hearing on the floor.

Aaron Singer

00:16:38 - 00:17:07

Yeah, I think— yes. I also like knowing that reps are not straightforward about this, about their lack of control. I feel like leads to this issue of you think your rep has more power than they do, when really you just get the speaker on your side and stuff happens.

Jonathan Cohn

00:17:10 - 00:17:31

What's so funny about that, that I feel like there's the perennial dynamic amongst any legislator, is that they are so powerful when they want to talk about something that they got accomplished and that it is because of them and their sheer force of will. But if it is something that has not happened, they're like, I'm just one person here. What do you expect me to do?

Aaron Singer

00:17:31 - 00:17:32

Yeah.

Anna Callahan

00:17:33 - 00:17:36

Failures are someone else's fault. Successes are definitely theirs.

Jonathan Cohn

00:17:36 - 00:17:39

But then we design systems that really do enable that.

Anna Callahan

00:17:40 - 00:17:40

Yeah.

Aaron Singer

00:17:41 - 00:17:42

Yeah.

Anna Callahan

00:17:44 - 00:17:55

All right. I mean, we would take any other stories that you have. Do you have anything that's just funny or interviews you've done that were surprising?

Aaron Singer

00:17:56 - 00:18:32

I'll say the story that I have coming out this week, I showed up to the 20th anniversary of Romneycare at an event which mostly featured legislators and insurance executives speaking together. And yeah, and learning, hey, that the RomneyCare Chapter 58 was not made with affordability as the priority.

Anna Callahan

00:18:33 - 00:18:40

You mean as a priority, right? Was it? It wasn't the top priority. Where was it on the priority list? Anywhere?

Aaron Singer

00:18:41 - 00:19:03

Yeah, they didn't give like an exact ranking on this, but they openly said like, hey, we are not going to— this was not a concern for us. We said we were going to tackle this later. And yeah, I was shocked that they would openly admit that. But yeah, so that's a story coming out in about a week or soon. We'll see next week, I think.

Jonathan Cohn

00:19:03 - 00:19:11

And I feel like that speaks to the danger whenever they say, oh, we'll get to that separate issue later, because do they? Yeah.

Aaron Singer

00:19:13 - 00:19:14

Yeah.

Anna Callahan

00:19:15 - 00:19:15

No.

Aaron Singer

00:19:16 - 00:19:17

They don't.

Anna Callahan

00:19:19 - 00:19:20

And yeah, go ahead, Jon.

Jonathan Cohn

00:19:21 - 00:19:28

No, no, Anna, go ahead. Oh, I was like, any other kind of stories from the experience that really stand out to you?

Aaron Singer

00:19:30 - 00:21:03

I'm trying to think ones that I can share, ones that are— a lot of the stuff that I've uncovered is not I can't talk about either because there's some information that I know that I should not know. But I will say this, anyone who wants to do what I'm doing and you just show up as a total outsider, and just look around and ask questions, it gets you so far because you don't, you really, like, you know, the whole, to anyone that's in the system, it doesn't seem crazy to them. You know, like it seems like, hey, this is normal everyday stuff. But when you're outside the system and then you start looking in, you have a very different viewpoint. And There is so much content that you could print with news. More people should be going, especially people that are not trained journalists, people that are not— I mean, look, follow the journalist standards, but go in and just report what you see. A lot of times the people that seem to go in are blind to the same things that The current reporters are blind too.

Anna Callahan

00:21:04 - 00:21:14

And can you talk a little bit about the media? Like, we have media here in Massachusetts. Are they not covering it? Are they covering it badly? Are they covering it biasedly? What do you think?

Aaron Singer

00:21:15 - 00:22:29

Yeah. I think there's some reporters I think that are doing a really good job. But I think overall the trend is, at least with the Boston Globe, they'll have these kind of big stories. Where they'll talk about campaign finances or let's say the control that the speaker has over legislators. They'll do these one-off big stories, but then in their normal everyday reporting, they won't mention that as, hey, when a new law gets passed, they don't mention that, hey, it was literally just the speaker said, hey, we're pushing this through. I feel when that process is left out of it, people don't understand how these laws are really passing, and they're not able to effectively advocate for what they want. I think there's other examples in the globe where it doesn't seem great, some of the reporting where it seems almost like they're hiding stuff. But I have upcoming reporting on that too. But yeah.

Jonathan Cohn

00:22:30 - 00:23:10

When you were talking before about just going in and observing things, it reminds me of in the early days of Act On Mass, I remember Matt Miller would sometimes just go and sit in the House, the public parts of the House chamber, just to watch, to see what do you catch by just watching them do normal business. Straight up. Like, that is, that is like to the, to like most political journalists is probably just like you've seen, you feel like you've seen all of this already and you zone out. But if you are not somebody who goes typically and you go like, what are the things that are like, wait, that's what they're doing? Or like, that's how that's done. That becomes, that becomes kind of, that becomes surprising.

Anna Callahan

00:23:11 - 00:24:11

I wanted to make one little comment too about what you said something about like people inside the building. They don't realize. How much they've changed and how the way that they just normalize things that are not normal to us outside the building. And I was recently talking to a state rep and we were talking about different policy issues. I was talking about the difference between policy issues that I am fully supportive of, are progressive and help people, but don't actually change inequality at all. And policy issues that literally would redistribute some of the wealth like the kind of difference between those. And the response was, yeah, but there's all these, you know, there's big lobbies against those things. Like there's— this industry is against that and that industry, like the realtor industry is against the, you know, the housing stuff and the insurance industry is against the medical stuff. So what are we to do? And like, it's so interesting to hear that framing. And, you know, you come away with being like, what do you mean?

Jonathan Cohn

00:24:11 - 00:24:12

So what?

Anna Callahan

00:24:12 - 00:24:37

Like, why are you doing what they want instead of what we want? Like, How can you just say— and I'm sure that there's more in there. I'm sure that there is like, because there's a long, like, because the industry is against it, then these things happen, which means the blah, blah, blah. But like the just flat out saying, well, the industry is against it, therefore why try? I was just like, what?

Aaron Singer

00:24:37 - 00:24:52

Yeah, totally. Exactly my experience. Like, I just, I I did not know that people give up on issues before they even try, for those reasons.

Anna Callahan

00:24:53 - 00:24:53

Right.

Aaron Singer

00:24:54 - 00:24:54

Yeah.

Anna Callahan

00:24:55 - 00:25:05

Okay. Tell people how can they get involved. First of all, they can go on your Substack. You want to tell us a little bit more about that? And then how can people donate? How can people find out anything?

Aaron Singer

00:25:06 - 00:25:50

Yeah. So the Substack is Shadows on the Hill. Yep, just like the documentary. That's probably the best place to follow me right now. That's where all of my new stories are coming out. It's kind of just the center of where everything I'm putting out is. I'd say follow me on the Substack. If you want to donate to the film, you can go— the easiest way is probably go to shadowsdoc.com. There's a button on it. I think it says something like donate now or something like that, that will take you to the fundraising page. But yeah, I would recommend following my articles because they're pretty good.

Anna Callahan

00:25:51 - 00:27:19

Amazing. And for my fundraising pitch, I'm going to say donate to his documentary. I don't know, Jonathan, if you're going to be mad at me for that. We appreciate all of our donors. We appreciate anyone who donates to Aaron's film. We appreciate people who are helping all of us to get word out about this deep dysfunction. I mean, I got to tell you, I am, and I know many people who are so concerned about democracy in America. And it's not just the federal level, because if people had a belief that their local and their state governments were actively helping them, then there would be some buffer. First of all, we probably wouldn't be in the situation at the federal level, but also there would be some buffer. But the problem is we just don't believe that there's doing anything for us. And the reality is they're not. It's not a mistaken belief. Our statehouse is deeply, deeply dysfunctional and does whatever these giant financial interests, moneyed interests want. And that is so damaging to our democracy. I encourage people to check out Aaron's work. I'm going to give everybody a link before we do our final close-up. I love to do final thoughts So Jonathan, I'll let you go. I'll go. And then Aaron, you'll have the final, final word here on the thoughts about doing a documentary on the statehouse.

Jonathan Cohn

00:27:20 - 00:27:58

I'll just note that you're kind of riffing just then, Anna reminded me of the point that you so often see the percentage of people supporting a candidate and the percentage of people supporting like some progressive policy that the candidate's backing. Like you will always see more people supporting the policy than the candidate. And I think part of that, some of it's people's priority ranking, but also there's a big like mistrust of government actually being willing to do any of the things. And it's why the work of accountability, I think various types of accountability and watchdog stuff is important because we need to show that there are problems so that they get fixed. It's not just to show that there are problems just for the sake of showing problems. It's showing the problems so that people actually fix them.

Anna Callahan

00:27:59 - 00:29:14

I just want to say that like part of why I've been running this podcast for like 6 years or more, I don't know how long, a long time, and why I talk about democracy at the state level, why I did years of work on democracy at the local level and still deeply involved in that, is because if you don't act to— if the government doesn't actually pass policies that help, at this point, reduce inequality, let's just be real, right? If we do not make that happen, we are effed. We have to make this happen. It's crucially important, I think, for people to check in not just to this podcast, but also to Aaron's work, that we elevate people who are really doing the great work to change the culture of our statehouse so that it in fact represents the rest of us and not these moneyed interests. That's my word on it. It's not just the state, it's work on the state to save our national democracy. Of course, we are the 800-pound gorilla in the world, So world democracy as well. So Aaron, you get to find a final word.

Aaron Singer

00:29:15 - 00:29:59

Yeah, I think I would piggyback a little bit off of kind of what you just said, the importance of smaller media places, specifically this podcast. You know, I reached out to you guys first because I'm a fan of the podcast. The stuff that you guys talk about does not get reported very well in most places. And So, you know, that's why I reached out to you guys first. That's why I've interviewed some of you guys. And, you know, and it's why I'm pushing so hard on my thing is because I want to do what you guys are doing, putting out more information and allowing people to better understand how government works. And yeah, thank you for the opportunity for today.

Anna Callahan

00:30:00 - 00:30:15

Our pleasure. Thank you so much for all the work you're doing. Thanks for coming on the show. Thanks to all of our listeners and our donors. We couldn't do it without you. Please do forward this episode to your friends and family, and we look forward to chatting with you all next week.