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Burn the Boats is an award-winning podcast featuring intimate conversations with change-makers from every walk of life. Host Ken Harbaugh interviews politicians, authors, activists, and others about the most important issues of our time.

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Ravi Gupta: “The Door is Always Open”

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Ravi Gupta: “The Door is Always Open”

Ravi Gupta held several positions during the first term of the Obama administration, including Special Assistant and Speechwriter to Susan Rice, the U.S. Ambassador to the United Nations.

After serving in the Obama Administration, Ravi wanted to take a break from partisan politics and do real work on the ground. He Founded RePublic Schools, a network of charter schools in the South that provide quality education to underserved communities.

Following the election of Donald Trump, Ravi decided he had to help fight Trumpism. He founded Arena, an organization dedicated to convening, training, and supporting the next generation of candidates and campaign staff. Arena has helped to elect over 75 candidates, and trained over 1500 staffers.

In 2019, Ravi Co-Founded Second Chance Studios, which teaches life, social, and professional skills to formerly incarcerated individuals. SCS provides courses in editing, social media, podcasting, and other topics in the media space.

Now, Ravi is the CEO of Lost Debate, a non-profit media company he founded in 2021. He hosts several podcasts, including Majority 54 which he co-hosts with Jason Kander.

You can find Ravi on Twitter at @RaviMGupta.

Ken Harbaugh: Hi everyone, it’s Ken. Before we start, I want to share some exciting news: We’ve paired with Meidas Touch, so you can now watch these interviews on YouTube. Just search for the Meidas Touch YouTube channel, or click the link in the show description. Thanks, and enjoy the episode.

Ravi Gupta: I spend less time being like, “Alright, I'm going to hold you accountable for all these things you've done,” especially when you're talking about family members, voters, things like that versus like members of Congress or something. But just to be like, look, the door's always open and if you decide to change your mind, it's not going to be this embarrassing moment where I'm going to hold it over your head. It's just going to be a welcoming conversation.

Ken Harbaugh: I'm Ken Harbaugh, and this is Burn the Boats, a podcast about big decisions.

My guest today is Ravi Gupta, former Obama administration staffer, and the host of several great podcasts, including Majority 54 and The Lost Debate Podcast.

He's also the founder of the Arena, an organization dedicated to training and supporting the next generation of candidates and campaign staff. Ravi, welcome to Burn the Boats.

Ravi Gupta: Happy to be here, big fan of you and this podcast and the state of Ohio. So, we get to kill three birds with one stone here.

Ken Harbaugh: Well, Ohio has been breaking hearts lately. Maybe we could talk about that in a minute, but it's been a while since we have caught up. What have you been up to?

Ravi Gupta: Like what you come to expect from me, I'm doing too many things at once right now. But I think in general, like you, I think I've just gotten the sense that there's a conversation happening often in the dark corners of the internet, that the right-wing is winning. And I've been spending a lot of time just trying to use media to have conversations in those places, try to take back the conversation and whether that's podcasting, YouTube, whatever comes next. I'm building a team out here in New York and working with others to just try to like get the message out across new mediums. So, this is the media phase of my life, I guess.

Ken Harbaugh: Well, you are very explicit in calling yourself a political eclectic.

Ravi Gupta: Yeah.

Ken Harbaugh: The Lost Debate Site is all about finding that middle ground and bringing people together, and that really is at odds with I think the main effort (at least from those in my orbit), which is to create a left-wing ecosystem to compete with the right-wing media ecosystem. We had Dean Pfeiffer on, who stressed the importance of trying to recreate on the left what the right does, so well. We just had Stuart Stevens talking about the same thing. How are you finding the Lost Debate project in terms of generating the kind of excitement that more naturally occurs when you're expressly partisan? It seems like it'd be really challenging when you're appealing to moderates.

Ravi Gupta: To use a metaphor, I keep two sets of books. So, I have my Majority 54 podcast where I'm just straight up partisan. I'm a Democrat, I speak to Democrats as Democrats, and I fly the flag for Democrats there. And then Lost Debate, in part because we're a C3, so by nature we can't be partisan. But also, as part of our mission, that's the podcast where … it's almost like primary general election, you know what I'm saying? So, like my primary is Majority 54. My general election podcast is Lost Debate, where I spend more time talking to people who are independents, persuadables, non-Trump Republicans, often, maybe some Trump Republicans, but I'm not sure.

But for that podcast, we have actually a more right-leaning audience. Our content is actually center, because my co-host is a conservative from the New York Post, Rikki Schlott, who's also 22-years-old. She's actually the youngest person ever to appear on Bill Maher. So, she and I just take big news items of the day and talk about them the way I wish most Americans would, in good faith being like, “Hey, here's what you believe. Here's what I believe,” where we'll try to persuade each other. We'll find areas for agreement and all that.

So yeah, I kind of get my fix of both parts of the politics there, but I'm still a diehard, even though I'm an eclectic, and my views don't always neatly line up with Democratic orthodoxy, I have no question when I head to the ballot box every year who I'm voting for. And we could talk about why, but like, it's not even a close call for me.

Ken Harbaugh: Well, I'm curious about the business side of things, and this is going to sound really boring. But there's a philosophical thrust to this question which comes from my disillusionment, having been in the podcast world for a few years now, at just how much more sticky and attractive the click bait-y episodes are.

Ravi Gupta: Oh, yeah.

Ken Harbaugh: The more partisan you get, the better they seem to do. And I'd like you to share your experience trying something in the middle. Is it worth it?

Ravi Gupta: Yeah. I'm very good at not making a profit, so I might be the wrong person to have on here. But Lost Debate is a C3, so we depend upon philanthropists and I view that as an effort that has to live outside of market economics in many ways, because we explicitly didn't want to go in and create the click bait-y stuff. We didn't want to chase our audience and just deliver like Buzzfeed style, cat video type content. We wanted to do what was right and build the audience (even if it took us time), in good faith and not be captive to it. And so, that is only possible to the generosity of our donors.

And then on the flip side, Majority 54 is a podcast that does work off of advertising. And for those, like the key is just to reach a certain size, from what I understand, where you can — I think the number tends to be 10,000 listeners for podcasts. Now, this could be two technical for people, but once you hit 10,000, you could start getting the traditional advertisers that people get. And once you do that, you could probably sustain yourself depending on what your budget is.

But there are people out there that are way expert on this kind of stuff, including your partner and mine and Meidas who are just very, very good at this, way better than I will ever be.

Ken Harbaugh: I'm glad you described the audience building the way you did, because that was my ultimate conclusion. And it has really paid off. If you speak from the heart and speak your truth, the click bait-y stuff isn't as attractive. And I don't think it builds loyalty the way what you're doing and hopefully what we're doing does.

But speaking of trying to find that middle ground, I remember conversations you and I had very early on in like the days after the 2016 election, and we're going to talk about the Arena now, in which you had this hope that maybe we could create, or you could create — I had to step away because I ran for office myself. But a political training and advocacy organization that supported moderates on both sides. Was that just a naiveté about how thoroughly Trumpism had co-opted the right, because that's not what Arena wound up doing.

Ravi Gupta: Yeah. The quick answer to your question is, yes, it was too naive. I think I came in thinking, “Alright, we're all going to be shocked by this and we're going to see people,” and I don't want to like totally dismiss people who fought back against Trumpism. But largely those people left the party, the Bulwark style people, the Tim Miller types, the people who just were like … Adam Kinzinger. You know there's a reason why you could just name them maybe on one hand, maybe two hands, and then you're done, with the people who were early on calling out Trump.

Now, there have been more and more people, and we could talk about what's happened lately. But by and large, I expected more from the Republican side than I've seen, partly because I spent so much time down south working with Republicans on education issues when I was running a network of schools down there, that I think I overestimated their level … because I saw them show courage on those issues. And I thought I would see them show more courage against Trump, and it just didn't happen.

So, then Arena became an explicitly partisan organization, and I really loved the candidates that we supported. A lot of candidates that — you were one of them, but also of Max Rose, Chrissy Houlahan, Elissa Slotkin, Lauren Underwood, Haley Stevens, Lina Hidalgo, a lot of people I look back on now-

Ken Harbaugh: You just listed a bunch of winners and me, I appreciate that.

Ravi Gupta: Well, I say none of them had as hard of a race as you did. So, maybe Colvin and Marilyn won, but like, there are just so few of them that had as tough a race as you did.

But when I look back at those candidates, especially that first group of candidates, they are all Democrats, but they're Democrats who learn to have a more inclusive message and win in very tough districts, a lot of them. And that is what I'm most proud of.

Ken Harbaugh: I think a lot of our listeners are probably already familiar with the Arena. I want you to give the top line bullets for those who aren't. But I also want you to share your bona fides here, because I think there's some weird overlap between our credentials in this conversation.

You come from a Republican family. You worked with a lot of Republicans in the South in Tennessee and Mississippi in education, I graduated from high school in Montgomery, Alabama. Tell us a little bit about your background and your (sympathy is too strong a word), ability to connect with that rank-and-file Republican voter, your dad.

Ravi Gupta: Yeah. Some of the people closest to me in my life are Republicans. So, my dad is a diehard Republican, and I would say a very, very Trumpian Republican. My brother is a Republican, Trump fan. Most of the people I grew up with are Republicans. A lot of my collaborators down south are Republicans. And so, I grew up in Staten Island, New York, which is as much of a 50/50 district traditionally as exists, but also, it's an Obama/Trump district. It's a district that has very much moved away from the Democratic party in the past 10 years, in a lot of ways that resonate with people who live in Ohio and places like that. And in ways that seem hard to move back, but I don't think are impossible.

And so, I grew up there, I had a kind of rough upbringing. And then I wound up going to State University of New York and really saw the power and promise of our public education system and our university system, and then went to Yale. That's where you and I met. And by that time, I was like a Democrat, but one who is always a little bit like … this doesn't mean what it means today, but we were Giuliani Democrats, my family-

Ken Harbaugh: No, that does not mean the same thing today.

Ravi Gupta: Yeah.And that's just who we were back then. I'm not saying that's — I have to examine going back now, what was true about him or not. But that's where we grew up. Everybody was a Giuliani fan, Democrats and Republicans where I grew up. And so, there was this ‘no nonsense’ way of doing politics, like make government work, get things done, straight talk. I could have very easily been a Republican if McCain had won the nomination in 2000, I think, and had brought his kind of brand of politics.

But I solidly became a Democrat, worked for Obama after law school or during law school and after. And then about one year into the Obama administration, I was working for Susan Rice as a speech writer, I just had this calling, for you it was the military. For me it was education in the South. I was just like, “I need to get out of partisan politics and do something useful.”

And so, I was just like, “Alright, I'm going to go work down south.” And my Democrats were some of my biggest obstacles and Republicans were some of my biggest friends down there. And I had just a wonderful experience running schools in some really red areas.

So, then when Trump won, I think that colored my optimism that I could talk to people across the aisle and we could come to agreement, but that surely didn't happen.

Ken Harbaugh: Well, talk about your reaction to that Trump victory. Mine was to call people like you and eventually to throw my hat in the ring. You built an organization that to this day, is an incredible force for training and preparing democratic candidates to fight back.

Ravi Gupta: Yeah. Very proud of the work that Arena has done. And I look back with a lot of pride over those first few weeks after that election in 2016. That's how I met Jason Kander, my co-host of Majority 54. That's how I met so many of these candidates. It’s how people like you and I who were friends, but who didn't spend a lot of time talking to each other in the intervening years got together and started talking a lot. And we built Arena, which for us, it started just as a gathering, three and a half weeks after that election in November, we rented a space in the Music City Center in Nashville, and we got like 400 people in the room. And we just got together to talk about what comes next. And people like Kander spoke, and Congresswoman, Stephanie Murphy spoke. Lauren Underwood when she was just a nurse coming out of the Obama administration spoke, Haley Stevens, all these people who came, and they were just people back then. They were saying, “I want to run.”

And so, we did that and Arena turned from a convener to an organization that supported candidates directly, and then eventually started running the largest training arm for staffers in the Democratic Party. And now we've trained something like 4,000 plus staffers through these five, six-day academies that we run around the country that train people on how to do discrete jobs on campaigns. And it's kind of a big tent.

So, in contrast to the way I was thinking about things in the beginning, which is this ideological organization that would advance a certain worldview, it became a place just for Democrats to come together and work together and be a place that's inclusive of people. Whether you're a Bernie Democrat or you're a Biden Democrat, or you're a never Trump Republican, it was a place for people to come together and just be like, “Alright, let's train to run candidates who run against Trumpism.” And we had a lot of people. And now we have our former law school classmate, Lauren Baer running it. She's been amazing. And I'm so excited always to see the young people and the young at heart go through that program and go on to do amazing things.

Ken Harbaugh: Can we talk about Yale Law for a second?

Ravi Gupta: Yes.

Ken Harbaugh: Because it was a life changing experience for me. Met some of the best people I have ever known at Yale Law School. But we're talking about the same institution that somehow was churning out people like-

Ravi Gupta: Josh Hawley.

Ken Harbaugh: Josh Hawley and J.D. Vance. Like, I get this question all the time. I don't have a good answer, so I'm hoping you'll help me. Is it just bad luck or is there something about such an ambitious institution that is grasping for credibility on both sides?

Ravi Gupta: It's weird because I’ve also struggled. Like the past five years, nobody's going to shed tears for Yale Law School right now, but the institution (and we probably won't go into this), it just seemed like it's lost this way over the past five years also.

But yeah, I don't know because you and I are not the traditional person. I came from Binghamton. I came from a very middle-class environment. Nobody in my family ever touched an Ivy League institution. So, to me, I just felt lucky to be there.

And when J.D. Vance wrote his book, I read it, I was charitable at first, because I saw it in many ways myself and his story, which is why I feel so offended by how phony he has turned out to be. Because when he wrote that book and he is like, “I'm this kind of whatever…” Now it reads very differently to me. But at the time when I first read it, I was like, “Oh yeah, okay.” Like I came from a family that didn't have a lot of advantages. I came from a neighborhood that in some ways felt like some of the things he wrote about. But then he turned out to be totally fraudulent. And how do you separate those people? I didn't know him personally.

I did know Josh Hawley. Josh Hawley and I would have lunch all the time together. Josh Hawley, I wouldn't go so far as to call him a capital M mentor. But we did spend a lot of time together.

And yeah, these institutions do create these people who are running from president from the time they could speak. And they were pretty recognizable back then, if we look back. Like he wasn't the guy who was going to hang out and like, be candid with you. And when you talk to Josh, he was very polished from the get-go. He's not exactly the kind of guy who's a fun guy to hang around with. And he was never vulnerable. And I think that's what I sense now looking back is there were some people like that who just never let their guard down, we’re angling for something from the beginning.

And yeah, there were Democratic versions of those and Republican versions of them, but God does it seem like there were a lot more Republican versions of them than Democratic versions of them.

Ken Harbaugh: It’s the appearance … oh God, this is such a loaded word, but the grooming that they received.

Ravi Gupta: Yes, yeah. There's all these background organizations. Like these groups that are like, “Yeah, you're the future of the party.” But then there are people who got a lot of that attention, like our buddy Jarod Morris, who turned out to be totally ethical, independent people who got all the attention from the same kinds of fed soc types or whatever, like my buddy Kellen Dwyer is like that too, who went on to serve as an appointee in the Trump administration. But by all accounts, like ethical dude, does the right thing, served as a lawyer at the Justice Department. Or my roommate from the Truman Scholarship days, Patrick Hovakimian, who stood up against the Trump administration in the Justice Department, in the final days, leading up January 6th.

Looking back, it's hard to know who going to be the truly courageous or not, you know?

Ken Harbaugh: Yeah, I do. Because frankly, some of the people who have stood up and yelled stop at the end of the Trump administration, well, even to this day, are the ones I would've least expected. The Liz Cheneys, for example.

I ask this question, it feels like every episode, because it's a fascinating study of human nature and character development: What do you think is the distinguishing feature? Stuart Stevens was our last guest. And of all people his-

Ravi Gupta: He's a good Mississippi boy, that Stuart. I spent a lot of time in Jackson. He's a hero down there. People love him.

Ken Harbaugh: Give us some insight here. What-

Ravi Gupta: Yeah, I don't know him personally, but he's beloved down there. I've always wanted to meet him. He seems like a great guy. But I think you have to believe in something. And I think there's a core group of people around John McCain who've turned out to be stronger on this kind of stuff. I feel like Nicole Wallace, for all of their problems, a lot of the Lincoln Project people like … and obviously they've had some issues. I'm not well steeped in them, but I don't want to fully endorse everything that's happened there, but they …

Like McCain was such a leader to me, that like the people in and around him were left with a sense of ethics. Now, I think like McCain himself was complicated in later life, but I do think he believed in something and he really left the people who worked with him with a strong sense of ethics. And I think they couldn't shake it, most of them. Like they couldn't let themselves do it.

Ken Harbaugh: Were you on the Obama campaign when McCain-

Ravi Gupta: Yeah. Very much. I was Axelrod's assistant during all that kind of stuff.

Ken Harbaugh: Alright. Set the stage. Some of our listeners aren't going to know what I'm referring to; you and I automatically are there.

Ravi Gupta: Yeah.

Ken Harbaugh: But that moment and then the campaign's reaction.

Ravi Gupta: Yeah. There were so many moments, there were a couple of things. One was he was in a town hall somewhere and somebody was questioning, I think it was like saying like Obama was a Muslim or something. And like a whole separate discussion as to why that is even used as an insult or whatever. But McCain, at the same time that Palin was basically giving a test run on the politics that we see today, he basically shut down this person and said, “Obama's an American. We have our disagreements and yada, yada, yada.” It was like a great moment. I'm not doing it justice.

Now since then, people have talked about, like there was another response, which is like we shouldn't be using Muslim as an insult. But it was his good faith attempt at diffusing that. He also decided not to use the Reverend Wright attack against Obama because he felt like it would be racially charged.

So, it was a different kind of politics. You mentioned Liz Cheney, interestingly enough with her, I never thought I would say this, because I spent so much of my youth defining Dick Cheney as the most evil adversary that we had. And I don't want to let him off the hook for some terrible things he did. But he does also in a weird way, have his own belief system that he instilled in his daughter about service. And I think Trump was very offensive to the Cheney family. And so, I think in that sense, like there's like these little camps, McCain, Cheney and all that, and those are very different people. I don't put them as equivalents.

But it's incumbent upon people like us to leave the next generation with a belief system. Not just about like, what do we do about education? What do we do about healthcare? But like, how do we even conduct ourselves when there are hard choices? And what does it mean to take the hard choice over the convenient one?

When you look at the Stuart Stevens’, and the Liz Cheneys, and you compare them to the Josh Hawleys and the J.D, Vances, that's what separates them. Not like some like worldview that it has to do with what the tax rate should be or whatever, but just what does it even mean to be courageous?

Ken Harbaugh: Is there a way to apply that understanding to the less sophisticated Republican voter, even the MAGA diehard, because I feel like there has to be two different accountability standards, for those on the inside who pay attention to politics, who know that Trump is behind the orders to put kids in cages. And then (if you don't mind me getting personal here), people like your dad and your brother. How do you think about (and I say this as someone with Trump voters in my own family), their moral responsibility for supporting this person?

Ravi Gupta: Yeah, it's tough because you almost — and you have to treat them differently than people in real positions of power who've done certain things. It's almost like we have to leave the door open, is how I see it. So, I spend less time being like, “Alright, I'm going to hold you accountable for all these things you've done,” especially when you're talking about family members, voters, things like that versus like members of Congress or something. But just to be like, look, the door's always open and if you decide to change your mind, it's not going to be this embarrassing moment where I'm going to hold it over your head. It's just going to be a welcoming conversation. And it takes a lot of discipline to do that because obviously there's a part of me that really, really would love to do an ‘I told you so’ moment, but those never work.

So, the thing is my door has been open and the door of the Democratic party has been open and a lot of these people haven't even come near it yet, but you just have to keep it open. That's how I see it. And it's like up to the man upstairs in people's conscious and whatever belief system they have, to hold them accountable on some of the things that they've done. My job is to (especially for the average person), just be like, “Hey, you're welcome to come back at any point or just even come if you've never been here.”

Ken Harbaugh: So, Miles Taylor has argued very forcefully, and we just had him on too, that they're never going to come over, at least in the numbers that you need to make a difference in an election. And this was a surprising take for me, that the creation of the Forward Party isn't about really creating a third ideological lane. It's about creating somewhere for those Republicans to go, even if they do belong in the Democratic party, tribalism is what keeps them out of it. They're never going to make that switch. And why not give them just an alternative to the Republican Party, given that with the strength of tribal connections, they're never going to become Democrats. What do you make of that?

Ravi Gupta: Yeah, I think we've got to run some experiments, and I know it's really hard to do this because every election is so high stakes. But we're talking the day that Sinema switched to an independent and it'll be interesting to see if she decides to run, which it seems like she's setting herself up to do it. She's basically made the calculation that Democrats can't run a candidate, which in every way they will, because how do you stop them? But the Democrats are going to run somebody. And the question is, what does this do?

Most Democrats that I know, including Pfeiffer, believe that with Sinema and any Democrat on there, it could be a guarantee that the Republican picks up the seat. Which is why a lot of people like me, who are kind of independent minded, haven't embraced third parties as much as our ideological purity would love them. It's because the mechanics of our elections are so screwed up. So, unless you're in a ranked choice voting state or runoff state or something, it's really hard.

So, I like experiments. I cringe at the consequences of some of them. I wouldn't want those experiments to be the presidential race yet, but it's like, I don't know. Like Georgia was a good example of this where the Libertarian candidate got a few percentage votes enough to be dangerous. But then because it's a runoff state, it wound up not mattering really.

So yeah, I honestly don't know the answer. My sense though are whether there are people who call themselves Republican who switched to Democratic, there definitely are people who will vote one way or the other. There was a lot of split ticket voting this past cycle, not as much as we'd like, but enough to make a huge difference in a lot of the states. Look at Georgia for example.

Ken Harbaugh: Yeah. I think the counterpoint is that those voters the moment they perceive the immediate danger to have passed, they'll go right back. Even though the deeper danger is still there, which in my opinion is a Republican party that has grown fundamentally anti-democratic, in its outlook, in its strategies. And I think that's where Miles Taylor and the Forward Party are coming from in large.

Ravi Gupta: Yeah. And there are things Democrats could do. It's totally local. Like one Democrat I really love is Jared Polis. Like the reason why I think Jared Polis does so well and he crushed it, like there's so much attention to DeSantis, but Polis ran up the score in Colorado. And why does he run up the score in Colorado as a Democrat? Well, he has a state that is a little Libertarian leaning for a Democratic state. It's really a purple state. And he's like, “Alright, what am I going to do?” He's going to emphasize an agenda that connects freedom across a couple domains. So, he's going to talk about reproductive rights and freedom. He's going to talk about the right to marriage. But he's also going to talk about like, when it came to COVID closures and things like that, he was a person who followed science, but he also was pretty quick to reopen compared to a lot of other blue states because he was partially like, “Alright, this is a state where this sort of autonomy and freedom really matters to people.” And he also has cut taxes four times, since taking over. And so, he shows a lot of people who are skeptical of Democrats that, “Hey, I could be good with money.” And he's cut taxes while also expanding critical programs. He's just been good with money and like making government work for people.

So, I think like that's a good roadmap to say, what makes people go to Republicans? Is a question to ask. One of the things that makes people go to Republicans is they associate Democrats with higher taxes and poor government services. So, if we can get that right and say, we're not going to become small government trickle-down economics types people, but we're not just going to raise every tax we can and expand every program we can without any sense of effectiveness. We're going to like, have a keen eye for what works and what doesn't and be like really good stewards of your money. I think that makes a huge difference. If you couple that with some of the other things that we do that are very popular, I think that can go a long way in keeping people in our party.

Ken Harbaugh: That doesn't work in a state like Mississippi.

Ravi Gupta: Yeah. And it's totally different in different states. Like Mississippi's problem is the government is unquestionably too small. So, it's different than New York where it costs us 2 billion a mile to build subway. And like, there's like a hundred-million-dollar staircase in the subway. Or you can't even build public bathrooms because they're so expensive to build. In New York it's different than in Mississippi. And I think that's part of our politics, is like we've got … Arizona's a good example. The conversation around teacher pay in Arizona and the conversation around teacher pay in New York is so different. It's why it's hard to have a national podcast sometimes, because people will ask like, “Well, are teachers paid too much, paid too little?”

And I think that's part of our politics.Arizona's a good example. The conversation around teacher pay in Arizona and the conversation around teacher pay in New York is so different. It's why it's hard to have a national podcast sometimes, because people will ask like, “Well, are teachers paid too much, paid too little?” First of all, I don't think teachers are paid too much almost anywhere, but there's a way that they're being paid in New York that it's a different conversation than what's going on in Arizona, where we're truly committing an offense to the profession.

Ken Harbaugh: Do you think the Utah experiment, Evan McMullin, is replicable anywhere else? And just the refresher, you had a democratic party that did something extraordinary, which was not field a candidate knowing that its chances in Utah were non-existent and putting all of their hope on Evan McMullin running as an independent.

And we refered to Mississippi. In states where the Democratic brand is so damaged,might that be a way to challenge the extremist candidates that the Republicans are putting up?

Ravi Gupta: Absolutely. Now, Mississippi's an interesting case study because Mississippi actually should be a democratic state. So, it's actually, because of the black vote, they've been so disenfranchised. That's a whole other story.

But you take a state like Tennessee. I lived in Tennessee for seven years. When I got there, it was Democrats controlled the state legislature, the governor's mansion and had a ton of members of Congress. It flipped pretty quickly in the Obama years, which is an interesting question, what happened there? But it's not going to go blue anytime soon. And we've fielded some great candidates on the Democratic side in the past few years. We fielded Karl Dean, a very popular democratic mayor of Nashville as the governor candidate, and he got killed. And Bredesen, as the former super popular governor, as the Senate candidate both got killed. So, in that state, I do think independents could help.

Now the problem with running against Republicans in some of these states is that they're so tribal, that even an independent doesn't do it for them. But it's worth trying. And you may find the right state like Montana, although Tester definitely deserves the chance to run again, he's such a good candidate. But like you pick off these states, South Dakota, that had a history of voting for Democrats and maybe you can catch a state at the right time. Texas is a good example of a state like this, although I think Democrats could win statewide soon.

But you could catch a state at the right time where there might be some demographic change happening while you don't feel a democratic candidate. You put an independent in there, could work. It takes a lot of organization and discipline.

Ken Harbaugh: Well, that demographic change is certainly on the radar of Republicans and Republican legislators who have hit the panic button, when they look down the road and realize that they're not going to be able to win on policy, win on platform. And we got two Yale Law grads talking. So, this North Carolina sovereign legislature case making its way through the Supreme Court. Is that as big of a threat to democratic ideals as I think it is?

Ravi Gupta: Yeah, I just did a deep dive on this yesterday. So, a lot of people I respect point out that actually statutorily the thing that people are most concerned about, which is that these legislatures will send electors in the electoral college after the facts and steal elections, from what I gather is not possible given the law that the electors have to be chosen on election day. So, for that particular worry, it seems to me, unless there's some really sophisticated before the election shenanigans, we’re going to be okay no matter what happens.

Now, the bigger issue here is that this theory would make partisan gerrymandering so much worse and it's pretty bad right now. Because essentially what the theory goes is independent state legislature theory, which is, to recap for your audience; there's this case in North Carolina that the Supreme Court heard this week, where basically the state legislature passed these district lines for house of representative districts that were skewed as they've done in the past towards Republicans. The state Supreme Court ruled that the maps were unconstitutional under the state constitution and then used what they call special master to draw new districts that resulted in basically 50/50 congressional delegation. And the Republicans are challenging that map or that ruling, even though it's after the election, under this theory that has never been adopted by the Supreme Court in a majority opinion called the independent state legislature theory, which essentially says that in the constitution's elector clause, it says that, the time, place and manner of elections are decided by the state legislatures, not the states.

So, what certain people have argued, Clarence Thomas endorsed this view in a concurrence in Bush v. Gore, but certain people have argued that this means that state courts can't rule on their own constitutions and constrain state legislatures.

Now, sorry for all the jargon, but all of this comes out as saying like if the Supreme Court (which there seems a lot of justices that have tinkered, like who've flirted with endorsing this theory on this current court), if they endorse that theory, that basically means these state legislatures, a lot of cases who have super majorities can do things like write whatever maps they want, gut voting rights, et cetera, and that even their own state courts can't stop them. And this is a real threat. I don't think it's the threat in the way that with the electors in the electoral college it is, but I think it will lead to bad gerrymandering and other bad things happening in elections.

But interestingly, Harvard Law School, a professor there ran a simulation that showed that if they endorsed this theory, it actually would hurt Republicans nationwide more because there were certain big state elections cases like in places like New York that benefited Republicans.

So, if you look at the New York case, Democrats would've netted a bunch of seats if they used the map they wanted to use, but their own state court stopped them.

So, all of this is a long-winded way of saying like, it would be bad if they endorsed this theory fully. But it would have unpredictable consequences for which party. But there's some good people who think that there's going to be a middle ground that Roberts endorses that actually helps Republicans without endorsing the theory fully.

I can go into that if you want, but it's what I think is going to happen.

Ken Harbaugh: Well, I certainly hope it's not a full-throated endorsement of the theory and I don't care who comes out on the winning side. The idea of state legislatures overriding the will of the people basically on a whim, scares the hell out of me.

Ravi Gupta: Yep.

Ken Harbaugh: And that is what some Republican legislatures have been saying they will do explicitly. And I can't point to these-

Ravi Gupta: They're running on it. They're running on it, I promise.

Ken Harbaugh: They are. They are. And it's terrifying stuff. Part of that, and this has been a change in just the last few years, is the injection of crazy into the political dialogue. And the moving of the Overton window, the normalization of people like Marjorie Taylor Greene and Paul Gosar and others. And this may fly in the face of our assessment of Josh Hawley and J.D. Vance's impact on the political debate, but it's the lack of this … God, I got to find a better way to say this, but this elite filter, it used to be that parties filtered candidates. And they don't really do that anymore. And I think the midterms were a great example of just the worst candidates in a long time, actually making it through their primaries and being handed massive megaphones and just driving an insane kind of debate throughout the course of the midterms.

Ravi Gupta: Strangely, I think we took a certain swing in a certain direction in 2018, but I think we've now swung back now, where I actually do think that we are more disciplined now than we've been in a long time. And you see that in our candidate selection.

There are a couple states I would love to take back our candidates, but by and large we’ve picked good candidates. And some of it's institutional, but some of it's just ideological. I actually think the Democratic party is very pragmatic, when they look at candidates, they're like, “Who's going to win?” That's all we ask. Like at this point, that's all we as, pretty much, so-

Ken Harbaugh: But the Republican party is, has gone in the other direction.

Ravi Gupta: Yes. I don't think the Republicans come back anytime soon. They're going to try really hard to instill a certain kind of discipline, but they're too divided and whether Trump sticks around the scene or not, which it seems like he's going to be around for quite some time. But even if he wasn't, like it's just there are too many forces. It's not the days of old where people in a smoke field didn't pick the candidates anymore. And it's going to be chaos, I think for some time now because there isn't any one person picking these people.

Now, it might not be as bad as this cycle. I think this was maybe a high-water mark for crazy in terms of like, there's always going to be crazy ideas in the background. Like J.D. Vance and Herschel Walker wouldn't be that much different senators. It's just that Vance was better at like using his sophisticated education and whatever level of constraint he had or restraint he had to hide his cynical politics in something more appetizing.

Although even his version of that is way more sharp elbowed and I would say abrasive than the version of him would've been 10 years ago. So, and he only won because he ran in a state where it's really, really hard for Democrats to win. If he was in Pennsylvania, he would've lost.

Ken Harbaugh: Yeah. Well, to be clear, I'm not advocating for the smoke-filled room approach either. Well, I don't know what the solution is, but I think you see this clear difference between a Democratic Party where we have these debates about candidate quality and electability and temperament and on the right, it's just off the rails.

And part of that is the way small dollar donations have changed the primary campaign process. Part of that is Trump himself, I don't think there's a single diagnosis, but it has really changed the way these debates play out.

Ravi Gupta: Yeah. If they were smart, the Republicans, Charlie Baker would be their nominee or Larry Hogan, they would win in a landslide, but they can't help themselves. They get in their own way here.

This happened at times, there was that series of elections where Todd Akin and the witch woman from Delaware and some of these really terrible candidates were out there. But this was the worst by far that we've ever seen.

Ken Harbaugh: Yeah. Well, I know we got to let you go, but before we do any prognostications on ‘24, Trump has obviously announced, but do you see any type of effort to unify behind an alternate on the right?

Ravi Gupta: Yeah. I'm not breaking you ground here. I do think DeSantis is formidable. He's somebody who I think is different … I've argued with a lot of Democrats about this, because they're like, “Oh wait, until people get to know DeSantis, they won't like him, whatever.” I'm like, maybe, and there's like good think pieces about this or whatever, but he's a movement candidate, which works well within the conservative side. He stands for an anti-COVID closures, anti-shut down politics, keep the schools open. And then he's also like the crusader on CRT and all these like education wedge issue things, going after Disney and cultural institutions for their “woke bias” or whatever. He's a movement candidate and you beat Trump with another movement candidate. And so, I think he's got something to work with. He's obviously very popular in a very important state. The electability is going to be on the minds of a lot of Republicans and DeSantis has a case to make that he's way more electable than Trump. And in contrast to Cruz and some of these other people who ran against Trump in 2016, my sense about DeSantis is that he is not going to back down against Trump in these debates. His ego is too big. So, I think he's going to get up there. Trump's going to attack him, he's going to attack Trump right back. And it's not going to be like this phony Rubio type attack back, I actually think that DeSantis has a little bit of like this sort of schoolyard brawler in him. I'm getting out the popcorn. Honestly, I think it would be fun to watch. Obviously, it won't be fun, whoever comes out next, like whoever we're going to have to run against, like it's going to be a tough race. It always is.

But it'll be fun to see them tear each other apart. And the more those two go at it, the better it is for us, because it will leave some bruised, disaffected members of their own party and it will get ugly if they both stay in the race. And I think that will be really good for Democrats.

Ken Harbaugh: Well, let's leave it on that note. Ravi, it's great talking to you as always. Looking forward to coming on Majority 54.

Ravi Gupta: Yes sir.

Ken Harbaugh: Thanks again to Ravi for joining me. Check out the show description for links to Ravi’s podcasts, and make sure to follow him on Twitter @RaviMGupta.

Thanks for listening to Burn the Boats. If you have any feedback, please email the team at [email protected]. We're always looking to improve the show.

For updates and more follow us on Twitter @Team_Harbaugh. And if you enjoyed this episode, don't forget to rate and review.

Burn the Boats is a production of Evergreen Podcasts. Our producer is Declan Rohrs, and Sean Rule-Hoffman is our audio engineer. Special thanks to evergreen executive producers, Joan Andrews, Michael DeAloia, and David Moss. I'm Ken Harbaugh, and this is Burn the Boats, a podcast about big decisions.

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