Pod Save America - Debating the Trump Era with Abby Phillip

Episode Date: November 2, 2025

Who is worth debating? Where do we draw the line? Will all journalism eventually devolve into debate? Jon Favreau is joined by Abby Philip, anchor of CNN NewsNight, to talk about her viral cable news ...show, the battle between traditional journalism and punditry, and her new book on the presidential campaigns of civil rights icon Jesse Jackson, who rewrote the rules of the Democratic Party and helped pave the way for Barack Obama’s rise.For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast. Get tickets to CROOKED CON November 6-7 in Washington, D.C at http://crookedcon.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Starting point is 00:01:32 site, but I personally recommend their new dinner party pack or their duo gift set now available in glass if you want it. So head to graza.com slash crooked and use crooked to get 10% off your order and get cooking this holiday season with some fresh, delicious olive oil. That's 10% off your order at graza.com slash crooked and use code crooked. Welcome to Pod Save America. I'm John Favro. You probably know Abby Phillip as the host of News Night on CNN, where she expertly and gracefully moderates what you might call boisterous panel discussions that often turn into viral moments. She's also one of the most thoughtful journalists covering Trump or Trump. or at least attempting to right now.
Starting point is 00:02:30 And on top of that, she's also out with a fascinating new book that I'm loving, a dream-deferred Jesse Jackson and the Fight for Black Political Power about Reverend Jackson's groundbreaking presidential campaigns in the 1980s, and importantly, what those campaigns can teach us about where the Democratic Party is today and where it needs to go. For all those reasons, I've been really eager to have her on the show, and I'm so happy I was able to get some time when she visited L.A. on Thursday. Here's our conversation. Hope you enjoy.
Starting point is 00:03:04 Abby, welcome to Pod Save America. Hey, thanks for having me. A lot of people might know you from your job at CNN as the lead anchor and host of CNN Newsnight. But you're also the author of a brand new book, A Dream Deferred Jesse Jackson and the Fight for Black Political Power, which is now on sale. Yes. Exciting. We'll get into that in a bit. I just want to start with some questions about your day job.
Starting point is 00:03:26 You've been covering politics for a long time now. Yeah. Since 2010, 2011? 2010. Yes, back, I was young. You were in the White House. Yeah, I was going to say. We were both young, but I was younger, actually.
Starting point is 00:03:42 I know, no. Yeah, I mean, I was young enough that you had no idea who I was at that time. Well, you know, once I went into the White House, I didn't know who anyone was. I was just stuck in there all day. So you were a political reporter throughout the Obama administration, 2016 election, the highly functioning democracy that we've had since then. In terms of processing, analyzing, reporting the news, how does 2025 compare to everything before it? Like, do you feel like covering Trump's second term is just an acceleration of the craziness that's been building for a decade or does it feel like something new?
Starting point is 00:04:20 I think it is an acceleration of the craziness of the first term. It's like, obviously, they had a lot of time to think about this stuff. They learned from their mistakes. And so a lot of things that are happening now are things that they wanted to do then, but they couldn't because they couldn't figure out the government. They couldn't get their act together. And now they're doing it. And also, Trump is so much more in control now than he was then. I mean, he does not have a functional other branch of government in Congress.
Starting point is 00:04:50 And so he literally can do whatever he wants. And it shows. And so, I mean, the first time around, it was like covering a lot of hijinks. It was like a government that was just a bunch of people who wanted to do a lot of things, and then they couldn't quite figure it out, and something always went wrong, and it was always just this almost like a clown show. And I think this time there's, there are definitely some clown show elements still present. But they're much more organized, and it's much more serious because I think they're thinking longer term.
Starting point is 00:05:21 I don't think they were thinking that long term. Trump was in the office the first time because they weren't sure whether his politics were going to be lasting. And now we know. And I think now they're thinking about, okay, how do we really change this country permanently? And that's what we're operating on. I find it harder to somehow keep up with the news this time around than even last time. There's more happening for sure. Yeah. There's more of, and like, there's more of consequence happening. Yes. Like last time if you missed the scandal or the outrage of the day, it's like, we'll have another one, whatever. It'll pass. This time it's like, oh, well, we should cover that because that's actually going to have a
Starting point is 00:05:58 real impact on people and people might not be paying attention to it. And I also think, the thing I think about actually is the stuff that we're not covering. It's the stuff that's happening that we don't really have eyes on because they've gotten much better at keeping journalists sort of away from the nitty-gritty details of what's happening in the government. I think that's the stuff that kind of keeps me up at night is that we don't, I think we have less visibility now than we did before into the inner workings of the government, into even Trump's world. I find that the reporting this time around about, and I don't, I'm not a sort of day-to-day Trump reporter anymore, but the reporting that we have now about what's really going on in the White House, the deliberations,
Starting point is 00:06:46 the conversations, who's influencing the president, how he's weighing in on things, is much more limited than it was in the first term. And that's their consequences to that. I think we know less. I think there's still just as much happening, if not more, but we know less about it. How do you feel about what's happened to the press pool in the White House? Because, you know, I just feel like there are, you know, Caroline Levitt and the staff are going to do what they do at briefings and just sort of deflect and whatever else. Trump, sometimes when you're asking him questions, you actually get some interesting answers into his insight. And I just feel like, aside from Caitlin that you, Collins, who you work with, and a few other reporters, we're just
Starting point is 00:07:29 getting so many fewer real questions when he whole, even though he's holding more press availability, you're getting fewer questions that are not just congratulating him. That's on purpose. Because you know that they, I mean, when they basically tried to take over the accreditation process for a White House press pass. The goal was to fill the seats with people who were sycophants. And they have done that pretty successfully. I mean, they call it new media, but these are all just, it's all Trump media. And so that's why, I mean, I get frustrated when people are like, the media is not doing anything, but they don't realize that the nuts and bolts of who's in the room matters and is now more controlled by the White House than it has ever been.
Starting point is 00:08:14 And so it's not the fault of the day-to-day reporters who are still asking questions and are still doing their job. It's just that now the deck is stacked. Like the room is packed with people that they handpicked because of their loyalty to Trump. And that is completely shifting what comes out of these press briefings and media avails. And, you know, at the end of the day, you've made the point about Trump taking questions. I think Trump actually likes the back of it. forth. He doesn't mind getting the tough question from Caitlin or whatever. And he takes them because he knows it makes for good TV. And that's probably the one thing that is still kind of
Starting point is 00:08:53 allowing the system to somewhat get information out of this White House. Yeah. It's obviously been a rough decade for journalism as an industry. Corporate consolidation, mass layoffs, audiences now can get information from a million different sources, many of them for free, many of them not trustworthy. Trust in media is at lowest level ever. And then Trump comes along, and especially in the second term, backs up his rhetorical attacks on the press that were a hallmark of the first term with frivolous lawsuits, FCC threats, making sure his allies have influence over certain outlets. What are the conversations like between you and your colleagues about the future of your profession? Well, I mean, the truth is, I don't have a ton of conversations about this
Starting point is 00:09:49 with my colleagues. I'm not joking you. I just think we're literally just working. Just every day. Every day. And what are we going to do? You know, we're kind of in a place where we don't have a lot of influence over the moves that are happening above us. So all we can do is what we know how to do. I do, I think, about this more broadly than in the media, because the media is just one sort of cog in the capitalist system. And consolidation usually is not good for marketplaces. And I don't think it's necessarily great for the media. I think that we are in a place where a lot of consolidation needs to happen for financial reasons, but the loser is going to be the consumer of information. And it also is probably going to push more and more of those consumers to alternative media sources.
Starting point is 00:10:44 And so that's just looking at the industry broadly. That's how I see it. And can I do anything about it? No. Can I do my job? Yes. And so I'm going to do my job. And I really do think that we can sit and complain about it all day long.
Starting point is 00:11:04 but we have to just be able to have enough freedom to do the day-to-day work. And I still feel like I do. I look at a lot of the places where there are concerns about who owns them and what kinds of corporate top-down mandates are they under, places like the Washington Post, places like the Wall Street Journal. And they're doing excellent journalism. They really are. And so I just think people are going to need to be.
Starting point is 00:11:34 make money. And they are going to. But the broader themes that are going to drive what media looks like is actually the fact that there are going to be a lot of different places that people get information from. And the mainstream media consolidation that's happening right now is only going to hasten that shift. So we just have to be honest about that. And, you know, I think we all try to play in the pool of the new media landscape and do what we can. But that is, that's a shift that's inexorable. We're not going to stop that, and it's only going to go faster and faster. I wonder if you worry about, I do, and as someone whose job relies on other journalists doing this excellent reporting, that, you know, people are going to, consumers are going
Starting point is 00:12:21 to think, okay, you know, I'm watching punditry and analysis, and am I really going to pay for, like, original reporting? Like, I worry that sort of the balance with the incentives for actual journalism and reporting, you know, have gotten to the point where punditry is easier, cheaper, and more interesting sometimes to people. Sure. But I, it's okay. Like, I think it's fine. We can walk and chew gum at the same time. You know, because I think people like to crap on, I don't know if I can curse. Can I curse? You sure can. People like to shit on context and analysis. And you can call it punditry. You can call it whatever you want to call it. But I think that.
Starting point is 00:13:02 that what the, what the marketplace is saying is that people are hungry for help understanding. Yeah, that is true. And information is everywhere. It is ubiquitous. So it is okay and good and normal and commendable that people are saying, help me understand this. And I don't think we should be on our high horse and be like, okay, the only thing that matters is that we just keep feeding you from the fire hose. People really want to, um, they, they want to, um, they want to, comprehend this moment. And we need to be able to give people both of those things at the same time. And yes, it is cheaper, sometimes literally and figuratively cheaper to do it that way. You know, I mean, I think that there is so much bad that can happen when it's just like a lot of
Starting point is 00:13:53 people spouting their opinions. But I also think that doing that with integrity counts. And we should not be out of the game of that. So, and leave it to the crazies on the internet to provide this, you know, skewed so-called context. And so I think, and having done this in a lot of different parts of the media world at this point in my career, that we have to provide a whole menu of options to people who are consuming information. And it is not enough to just say, well, this is good for you so eat your broccoli um no like people people want a range of things there's nothing wrong with that there's there's nothing to look down on and context is hugely hugely important that's why opinion pages exist in newspapers because some you know people have points of view and it
Starting point is 00:14:54 helps people digest the facts so that's my you know that's my little um soapbox I just think we can't be, we just cannot be on this high horse about this stuff. We have to give people what they really are craving, which is both the news and the context. Yeah, I think you can make an argument that in this media environment where there's so many choices that context and curation are like more important than ever. Because it's hard, right? When you're just like scrolling through a bunch of stuff, bunch of headlines, you don't know what's true, you don't know what's not. Like, it becomes more important to have some trusted voices that you know can help you make sense of the day. And, I mean, when you leave it to the crazies and they're out there, all they're doing is just sitting around and they're spinning these webs of conspiracies in which everything is just so conveniently linked together.
Starting point is 00:15:47 And it makes perfect sense. And I think that is so dangerous when we seed all of that space to people who have no moral compunction. about just staring people wrong. And that's, I see a lot of that happening, and that is really one of the scarier parts of where we are. Positive America is brought to you by Quince. Cold mornings, holiday plans. This is when I just want my wardrobe to be simple.
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Starting point is 00:17:28 staples that last this season with Quince, go to quince.com slash crooked for free shipping on your order and 365 day returns. Now available in Canada, too. That's QI-N-C-E.com slash crooked. Free shipping and 365-day returns, quince.com slash crooked. I want to ask you about your CNN Newsnight role as anchor, debate moderator, seemingly kindergarten teacher at times. First of all, I just want to say, like, you make an incredibly difficult job look easy because I'm not sure people fully understand like how difficult it is to moderate a contentious panel like that in a way that is I think fair but still firm because you have to pick your moments all while like fact checking in real time and offering
Starting point is 00:18:19 your own analysis is there anything in your background or experience that helped you prepare for this and I'm just curious like what you do to prepare for the show every Yeah. I don't know. I always say that I, like, I come from a really big family. I'm one of six kids. And I'm just really used to being in the middle of a lot of chaos. It's just, and also a lot of people with different points of view. And I do think, I know it sounds kind of cliche, but I really do think that that helps because I've, I've always just been able to deal with a lot of different personalities. I mean, we, my siblings and I have the same. two parents, but we're all different, every single one of us. And you have to, I love them. They're my family. And when we sit at that table on Newsnight, I think that the goal, what I'm trying to create is this sense that we can have this debate. We can, you know, correct each other and question each other and call each other out and still sit in the breaks and not want to smack each other. Now, every once in a while, you know, people go into the breaks and they're still bickering
Starting point is 00:19:33 and we're just like, okay, calm down, you know. But the goal is to have the ability to do that at the very least. And so, I mean, I think I'm also just not that person. Like I, I'm all, I'm down for a good debate, but I'm not the first person who will get heated in a debate. And it just so happens that I think works in this context because I'm more than happy to let them have their emotional ups and downs. And I usually try to not be at that emotional register because I just, it's not, it's not how I roll just on a deeply human level. And the times when I do, when it does turn up, the dial does turn up for me are rare and I try to keep it as rare as possible. So I think it's just helpful that my personality is just not that. And I mean, it used to be that people would be
Starting point is 00:20:30 like, oh, she's too, like, even keeled or whatever. And it just so turns out that this format works for me right now. So there you go to all my haters. I was going to ask, like, are there times where in your head you're thinking, okay, I should, maybe I should step in or if I don't, I'm going to get shit from people. Like, how much does that enter your? Yeah, I mean, And, like, transparently, we've been doing this way, this version of the show for a little over a year. And at the beginning, it was, we had to play, I had to play around with it. How much am I involved? How much am I correcting?
Starting point is 00:21:09 How much am I fact checking? Do I really want to be fact checking all the time? Do I really want to just sit back and let them talk? Like, what is my role? And I think there's a negotiation that happens there. And, you know, there are some things that I don't, I don't fact check. maybe because I don't know, it's come out of nowhere. People do bring things up out of nowhere.
Starting point is 00:21:29 And I'm just like, I've never heard that one before. And then we have to go back and be like, what was that all about? So I'm not always able to, I'm not a computer, but I am very well read and prepared for a lot of the arguments that come up. So I miss things. And, you know, people will still give me shit for missing things. But I'm a human being and we are in a live setting, right? Like, we're not scripting these debates. We don't even have questions.
Starting point is 00:21:58 We'll just go at it. We just, we have, we have information. We don't have questions. So we come to, I come to the table every night with a list of, you know, conversation aids. And the, but the conversation goes the way that the panelists take it. Yeah. And you have to be comfortable with a certain amount of unpredictability. and I think that I have more recently found, I think, a good balance, right?
Starting point is 00:22:31 It's, it's, I see myself as trying to play the role of like the incredulous questioner on behalf of the people who are at home and are kind of like, do you really believe that, you know, or just that's completely illogical. Or how do you square that with this? And I think that some of these, so some of the role that I play is just impressing people, just in kind of testing the argument and forcing them to defend it and forcing them to see it through its natural logical conclusion. And I think that's where I've landed so far. So far, but it's always shifting. It changes every single night.
Starting point is 00:23:14 And we are always bringing new people on who have, you know, it's always something new. And that's great. That's what's nice about the show. It's funny. I think the only time I've been on a, or the last time I've been on a panel at CNN that was like people on the left, people on the right. It was years ago. Yeah. And I just remember watching people go at it as like it was live. And then we went to a commercial break. And I was sitting next to Glory Borgier. And she was like, you know, you can jump in. They like when you jump in and mix it up. And I'm just like, this is scary. You know what happened? You know what happened? During COVID, people stopped being able to. to do it. Because everybody was in these boxes. And so the fact that we have everybody in the studio every single night is for, and it's for a lot of people, it's kind of a new experience. And they don't
Starting point is 00:24:01 get to do it that often. So a lot of people have to figure out how to talk to other people, like look them in the eye and say the thing and keep the same energy that they would otherwise have on social media. And I think that's part of the psychology of it too, is that you really have to be willing to, first of all, be on your feet. You have to be quick on your feet. And you have to be ready for anything. And you have to really be listening. Because, you know, a lot of times people are just, they have their little talking points. And they get mad at me when I'm like, I'm going to interrupt you because you're, you're answering the question that you want to be asked. And this is not that kind of show. So that's a skill that I think we have tried to call. cultivate, what does it look like to actually sit in front of a person you disagree with and talk to them and challenge them and be challenged. And the people who have figured that out have done really well on our show. And I think it makes for both good television and I think
Starting point is 00:25:04 it's an important thing to do. I've never been a huge fan of the debate, much of it on the left about, you know, platforming certain political figures on the right or legitimizing people on the right because you go on their shows because especially since I think most of these figures have large platforms already. But every time, you know, we've talked about this and every time I think about like inviting a like a MAGA person on the show to have that like in person debate. Yeah. The only thing that gives me pause is it's like it's hard to spend the entire time or I don't want to spend the entire time correcting or saying that's not true or let's fact check and then they fact check and I fact check and suddenly it's just like.
Starting point is 00:25:45 30 minutes of a fact check. Yeah. I hear you on that. And so it's like I do, I would love to have the debate about like deeply held beliefs that are different. Yeah. Sometimes it's hard to get past the talking points. I'm with you. It happens.
Starting point is 00:25:59 I mean, there are plenty of times where we've had people on and it's like, you're just doing your thing. I'm just throwing my hands up. Like, it's just what's the point? Because we can't have a debate unless we at least agreed to agree on facts. Like, facts have to. actually matter to you in order for us to have this conversation. Now, I also grant people that sometimes people have other facts that matter to them more. And that is okay.
Starting point is 00:26:28 Right, right. But there are definitely some people who are just living in a different world. And it's really hard. And it's not, and I think that is, yeah, definitely a situation in which it is very difficult, if not impossible, to have that conversation. And so you kind of have to find the right people who are willing to kind of level with you. in a at least at least in an open-minded way and I would kind of argue that that's not just unique to Republicans although I think their information silo is probably more enclosed off but it's but it's in general are you willing to concede something anything anything and some people are not
Starting point is 00:27:08 and so people aren't because I think there's this pressure that if you concede something on live on national television, then suddenly your side is going to be like, why did you just do that and what's wrong with you and you gave in? And it's a real. Yeah, it's a psychological thing. It's about social media cloud. It's about your standing in, you know, in the group. Yeah. You know, because the group, you're standing in the group becomes the most important thing to you. Right. Because your people might not like you as much anymore. And that, and that's, we have to come to terms with that in politics. That is such a big thing in terms of how people are willing to show up politically is that they're so afraid of being ostracized by people in their group that they're not willing
Starting point is 00:27:52 to admit when they're wrong or when something needs to change or when, you know, the other person might be right. Yeah. Well, and especially, I think on the left now, there's another reason not to do it, which is, well, if they're going to do this, then we can. can't be the ones that are always saying we're wrong, we change our mind, because we're in a fight against these people who are in a different kind of reality, you know? And it's sort of like, I think if you have values and beliefs and principles, they've got to be universal, like, no matter what the other side does. But do you, I mean, but I thought, you know, I've been talking about this a lot lately because I feel like this has really come up. And I mean,
Starting point is 00:28:31 I wonder, as you are a card carrying Democrat, do you, do you see that happening? And do you think that's a problem because I think some people think that Democrats unilaterally disarm too often and leave Republicans to just do whatever they want and then like in redistricting for example is an example of this. Yeah. Do you, do I think that it's a problem? Do you think that that's bad that Democrats are doing? Yeah. No, on that kind of thing, I'm like, that's an easy one for me just because it's like we proposed national nonpartisan gerrymandering and we couldn't get a Republican can vote for it. And if Republicans want to join us, then I'm like, let's stop the race to the bottom and do no more gerrymandering and let's reverse it. But otherwise, we're not going to
Starting point is 00:29:17 unilaterally disarm. I have a sort of a different take on the broader Republicans are always fighting and Dems don't fight. And the whole, like, you know, everyone likes to bring up the Michelle Obama quote. Like, you know, when they go low, we go high. And everyone's like, we can't do that ever again. And I'm like, it's not, I just think that our political goals are different. in a way which makes it asymmetrical like i think that donald trump and a lot of the maga movement would be quite happy if people were more cynical about politics and not paying as much attention and they would get to do what they want to do and i think that democrats at their best believe that government should be a tool for
Starting point is 00:29:58 people to come together across like different ideologies races identities and try to figure out something together and if you're going to believe that it's much tougher to then go and just destroy the other side all day because we believe in a bigger community than that. Yeah, I mean, I feel like the government shut down debate is a little bit of that where it's like, I mean, I was there all the years that Republicans shut the government down,
Starting point is 00:30:23 even when Trump was president. And in a way, Democrats have just, are just doing what they did and justified for all those years. However, the government is still shut down. Right. And people are still not getting paychecks and so on and so forth.
Starting point is 00:30:39 I think I don't have any answers to that, but I feel like that is the dilemma the Democrats are facing, which is do we really take on their tactics, even if people get hurt, or do we have a higher bar for ourselves? And what is what has heightened that challenge for Democrats is, of course, Donald Trump and particularly how he's acting in the second term, right? because I'm very much like, I don't want, I'm in politics so that people are helped and I don't want them to get hurt. But like, I also think that there's masked agents on the street, like arresting people who are American citizens and nothing stopping them. And I don't, like, my view on the government shutdown was I would not have gone, I would not have made it about health care. Because health care to me is a policy issue that under a different Republican president or a different president, whatever, you would say, okay, we had an election, they won, this is the government, they get to do what they want, right? People should feel the consequences of what they're going for.
Starting point is 00:31:40 Yeah, shutting down the government over a typical policy fight to me is not as important, I think, or I wouldn't have done it unless it was shutting down the government over, like, you know, I think Chris Murphy has been saying this, like, why am I going to fund a government that's like destroying democracy right now? Yeah. You guys can find the votes yourself. I think that, you know, my humble opinion as an observer of politics is I actually don't think that a government shut down over capital D democracy would have worked. I don't think it would have. Yeah, I think it would have gone way over people's heads. And this is not an endorsement of a government shut down over anything. Right, right, right.
Starting point is 00:32:20 But it's just to say that the uniqueness of this one, is that the underlying issue is one that is a political vulnerability for the other side, whereas the other stuff is much less so. It's true. Then if you get to the nerdy legislative part of it, though, you say, okay, why would we make a spending deal when they're going to go back after the spending deal and just be like, well, we're going to spend whatever we want? And we're going to not spend whatever we want, and we're going to shut down whatever we want,
Starting point is 00:32:49 fire whoever we want, and it doesn't really matter. And look, I hear that. But at the same time, I mean, some. deal has to be made. I know. I know. It's a tough situation. Do you feel like you better understand what drives maga politics because of this show?
Starting point is 00:33:08 Yeah. Yeah. You feel like you got enough of the like people's true feelings? I talked to tried and true, died in the wool, maga people every single day. And so. Yeah, I understand where they come from. I understand the information silos that they're in that make it hard to see outside of it. And it's not that complicated.
Starting point is 00:33:40 I mean, I think that they like winning. And Trump is winning in their minds. So in a way, to me, it boils down to mostly that. Because we have all shades of this sort of Trump supporter. We have people who are not really that into him, who are now, people who are not even all that into him right now, but would prefer to defend him to the alternative. You know, I see it all. And at the end of the day, the biggest thing that works for Trump is that they've figured out how to use raw political power to dominate their opposition. And turns out that's very appealing to a lot of people on the right.
Starting point is 00:34:20 And they're willing to, they're willing to gloss over a lot of conduct in order to be on the team that is winning. Yeah. So I think that's a lot of what's going on right now. Do you feel like you understand Scott Jennings' politics better? Yeah. I mean, he's, I think what I just described accurately describes him that, you know. Because he's taken a journey. He's been, he's not a on the.
Starting point is 00:34:45 Yeah, he's taken a journey, as we've talked about. I think he, as he said, he, he. would prefer Trump over the alternative, but I also think that he has seen Trump win on the culture issues, on the economic issues, on all of that. And he's willing to give him a pass on things that maybe he's slightly queasy about privately because I think he believes that going against Trump is a bad idea because Trump keeps winning. Pod Save America is brought you by Article. We love Article.
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Starting point is 00:37:13 So what was your sense of Jesse Jackson and his legacy before you started writing the book and what questions did you want to answer? My sense of him was what I think a lot of people's sense of him is, which is that he's an activist, he's a leader of the civil rights generation, and is ubiquitous, right? That he's in everything and that mostly it's just showing up. I think that was the sense that a lot of people had of him, half of him. And one of the reasons I wrote this book is because I've,
Starting point is 00:37:48 found that this particular chapter, when he ran for president two times, is arguably one of the most significant parts of his legacy that rarely gets talked about. And it is the part of his legacy that actually, I think, kind of undermines the view of him as somebody who's just sort of surfaced deep and only just shows up and so on and so forth, because I do think that running, you know this, running for president is a real, difficult task. And a little insane. Yeah, and it's a little crazy. And it attracts a certain type of person. And Jesse Jackson certainly is in that same category of people. But for a black man in the 1980s who grew up in the segregated South, who did not have much, for him to end up on the same
Starting point is 00:38:41 debate stage with all of these figures, not just Michael Dukakis and, you know, But Al Gore and Joe Biden and all these other people who later on went on to do other things. But he was on the debate stage with all of those people and holding his own on foreign policy, on economic policy, on a whole host of things. And then he comes in second place in 1988. And then it's kind of promptly forgotten about, partly because Bill Clinton, but also partly because Barack Obama. And I think that there's a lot there that is worth exploring. including explaining how we even got to Barack Obama. I think he's a huge part of that story.
Starting point is 00:39:24 Can you talk about that a little bit? Yeah, I mean, look, Jesse Jackson and Obama actually politically, to be honest, don't have a huge amount in common. So it's not so much about that because I think Obama is way more centrist than Jesse Jackson was. However, I also think Jesse Jackson's sort of left-wing politics of the 80s actually became kind of centrist in the 2010s or whatever. But more to the point, I mean, just from a nuts and bolts perspective, had Jesse Jackson not changed the rules of the Democratic Party
Starting point is 00:40:04 to make it easier for outsider candidates to come in and run against the establishment and still rack up delegates and still still. get to the convention, Obama wouldn't have been how we beat Hillary Clinton. Period. Yeah. We would not. It just wouldn't have happened. Yeah. If it was a winner take all like the Republicans have in the primaries, we wouldn't have done it. And I mean, in a way, it's like, think about the foresight of that because there were so many people in the 80s who were like, why run a black candidate for the presidency? You know you're not going to win. This country isn't going to do that in this moment. And they were right about that. But I also think
Starting point is 00:40:41 Jesse Jackson had this sort of tactical intelligence about the value of leverage. Some of that was built up for years and years of using leverage to get concessions from private companies on diversity and all kinds of other stuff. But he understood leverage really well. And he really pushed in both of those campaigns toward getting to the convention, getting changes to the platform, getting changes to the nominating process for the Democratic Party, the nuts and bolts of how you even get a candidate, let alone what that candidate stands for. And it turns out that foresight was exactly correct because 20 years later, and this is why the book is called A Dream Deferred, is because it took 20 years for this to actually, you know, be seen. But that became the thing that allowed Barack Obama to bypass what would.
Starting point is 00:41:38 have been a blowout from a much more establishment candidate. It's also the thing that allowed Bernie Sanders to have as much leverage and influence as he did in 2016 and in 2020. And so there's so much about how he conducted politics, and we didn't even talk about the issues. But all of those things make him a very consequential figure who doesn't get a lot of credit for that chapter in his life. Why do you think that is on the credit that he doesn't? Like he's not, he hasn't gotten his due, I think, either as a civil rights leader like a John Lewis or a political leader, not only from, I think, the public, but even from like his contemporaries. Totally. There's a lot of drama.
Starting point is 00:42:28 I mean, that's the truth, is that his relationships personally, I think, are very fraught. And I get into this in the book, that, you know, when he ran for president, he did not have many endorsements even from black elected officials. In fact, he had none in 1984. And in 1988, he had a few more. But overwhelmingly, a lot of his friends and colleagues, they endorsed the establishment Democratic candidate. And I think some of that has to do with not just the political part of it, but also just his relationships with people. And I think also Jesse Jackson is a character. He has like real main character energy in a sense that he has a lot of personality traits that are double-edged swords, this incredible skill of connecting and oratory and also an incredible amount of, I don't know,
Starting point is 00:43:34 know, a desire to be in the public eyes. Some people would say arrogance. Ego. Yeah. Not unfamiliar if you know people who run for president. Psychological turmoil around his father and how he grew up. And so there's all of that mixed together in this person. And so he was really polarizing. And I was talking to someone else just recently also about just the fact that he lives, he has lived as long as he has. Yeah. And that contributes to it too. He is 84 years old. And so for the last 60-something years of American history, people have known who Jesse Jackson is. Yeah. Very, very few people have that many years on the books in public life. And inevitably, that means that
Starting point is 00:44:26 you are going to have people who have all kinds of different views about you. All kinds of chapters of your life are going to get forgotten. And I think that just the longevity of his life has been a part of the picture. It's just very easy to lionize people when they leave us in an untimely fashion. Yeah, that's true. Because it's easier. You don't have to deal with the full scope of their life. And I think in some ways he was blessed to live a long life.
Starting point is 00:44:52 But I think the length of his life and the range of things that he did, sometimes works against him. You broke made me think, I was talking to some of my old Obama colleagues today. And I'm like, what? I don't have like a real sharp memory of Obama saying a ton about Jesse Jackson. There's a reason for that. Well, it's because what I remember is I remember that his daughter was Michelle's maid of honor at their wedding. So I was always like.
Starting point is 00:45:24 And Jesse Jr., they were very close. And Jesse Jr. was closed. In 2008, but before that. And then I remember towards the end of the campaign, there was a whole thing with Obama and... The hot mic moment. Yeah, the hot mic moment, where he was upset about how Obama was going to black churches
Starting point is 00:45:40 and he thought he was talking down to... I think he said, like, I want to cut his nuts out or something like that. I remember that being a thing on the campaign. Which, by the way, that's a whole thing in terms of like taking something that somebody says in a break and then publishing it. And then I remember Bill Clinton. inserting him into the Democratic primary when after Obama went South Carolina
Starting point is 00:45:59 and Bill Clinton was like, well, Jesse Jackson won some states too. God. I mean, that is. But I've never seen like, I don't think I remember hearing Obama talk about him. Yeah. Well, there's a very important reason for that.
Starting point is 00:46:17 And it's because their relationship was not great. And despite the Chicago talk, and the family ties and all of that stuff. I mean, I explore this in the book, and it's complicated. Yeah. Because I think that a lot of people involved in that have a lot of regret, are kind of confused about why it turned out that way. I think people acknowledge that Jesse Jackson and some degree of resentment played a role.
Starting point is 00:46:54 Yeah. Right? that Obama was, I don't know. I mean, I think the truth is, Obama allowed people, not him personally, but the fact of Obama was sort of a permission structure for people to sort of put Jesse Jackson to the side, or at least that's how he felt about it. And I do think that some of that psychologically played a role here. I mean, I talk to people on the Obama side and people on the Jesse Jackson side, people caught in the middle of the two. And I think that ego, right? Jesse Jackson wants to be remembered.
Starting point is 00:47:39 He wants to be honored. He wants to be given his due. He didn't always feel like he got it from both Obama and his team. He lashed out in certain moments as a result of that. In other moments, like in the hot mic moment, he was actually saying something that other people were saying, but it was unwise for him to say it where he said it and the fact that it became public was a huge problem. And afterwards, you know, he gave interviews where Jesse did, where he said, I regret that so deeply. Because the truth is, when Obama won, Jesse Jackson was related. I know.
Starting point is 00:48:20 I remember the picture of him in Grant Park with tears in his face. I mean, all of that said, when Barack Obama won, Jesse Jackson reacted the way a man who was standing feet from Dr. King when he was killed would react to a black man being elected president. disbelief, hope, fear, love, you know, and a little bit of regret that he wasn't able to do it, but joy that Obama was. And so those emotions were very real, and I think he had a lot of regret. He said so about how that relationship transpired. And I mean, your lack of – the fact that you don't have a memory of Jesse Jackson being part of the Obama world is because he really wasn't.
Starting point is 00:49:12 there. He hardly ever went to the White House. After the fact, they're both in Chicago, they've met. I wrote about a relatively recent meeting that they had. And that meeting meant a lot to him. It meant a huge amount to him because I think that he does live with some regret over that lost opportunity to have a relationship with the first black president, somebody who probably wouldn't be in the White House had it not been for what he first did. I also think even if they had had a close relationship, there was an effort on the campaign to not to make it a, you know, that he wasn't just the first, he wouldn't just be the first black president. Yeah. Like the history-making nature of the campaign was always intended to be a light touch and unspoken.
Starting point is 00:50:10 And, I mean, like, I remember we, he gave the convention speech. He accepted the nomination in 2008 on the day of the, I believe it was the 40th anniversary of the March on Washington. And there were a few consultants who were like, in the first draft, we had King at the end, and a light touch king, not like a heavy touch. And it was like, I don't know if we want to mention Martin Luther King. It's like a little too black. And I'm like, he is about to be the first black nominee of the party. And look, I think that that's a common theme. You know, when Jesse Jackson ran in the 80s, the fact that he came out of the civil rights movement was a problem because it coded radical to a lot of white Americans.
Starting point is 00:50:56 And I think, you know, the Obama campaign, and I don't want to speak too much, you're part of that world, but understood that. That for some people, you know, I think for most of us, we think, wow, these people are heroes. This was such an amazing time where we pushed the country into a period of reaching its true potential. But there are a lot of people who think civil rights movement
Starting point is 00:51:22 and they think radical black power activists. And it is politically very dangerous to be in that space. And Jackson couldn't avoid it because that is the history that he came out of. But even at that time in 1983, when Harold Washington was running for mayor of Chicago,
Starting point is 00:51:41 and Jesse Jackson was a really big part of helping make that happen. Even Harold Washington had to keep him at arm's laying. Because, again, like for the white Chicagoans who he needed for the general election, Jesse Jackson coded radical and civil rights and black power. And so even in the 80s, and he and Harold Washington were friends. He was kept at arm's length. So that was nothing new. And the fact that that did not really change after all that time, I think it just says a lot about the country and just how you have to navigate race and how you have to navigate the people who do have ties to those movements who were seen to have been asking for too much from particularly the white power structures that, you know, especially in the 70s and the 80s, controlled most of our politics.
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Starting point is 00:53:52 Head to Squarespace.com for a free trial, and when you're ready to launch, go to Squarespace.com slash crooked to save 10% off your first purchase of a website or domain. That's Squarespace.com slash crooked. The other reaction I had coming through the book was just this feeling of frustration and anger that there aren't many potential Democratic candidates today who have the ability, I think, like Jackson did, to speak from a place of passion and moral conviction about social and economic injustice, while also very explicitly trying to be. build a multiracial working class coalition going everywhere, talking to everyone, campaigning in pretty creative ways? Yeah. Did any of that jump out at you when you were? That's the thing.
Starting point is 00:54:52 I mean, that's the thing that you come away from this. You know, when you really dig into how that campaign unfolded, his unpredictability, his ability to kind of capture the moment. moment, to be creative, but also to speak to people in a certain way. I just think that the last few campaigns that I've covered, especially candidates who have run for president in the Democratic Party, they substitute reaching people on a sole level for a laundry list of policies. And I cannot for the life of me, understand why anybody would think that that's a good substitute. It's not a good substitute. I think it because it codes, if you don't, if you talk about morals and you're passionate,
Starting point is 00:55:48 it codes like too progressive. And that if you give you your laundry list, then it's like your laundry list of policies that poll well. And so then you can code more moderate. But like, I think it's a false choice. Yeah, it is a false choice. I mean, but also like, I don't know, politics is the art of persuasion. Yeah.
Starting point is 00:56:07 And you have to move people. You have to reach them. And we're moved by stories and emotion. Yeah, exactly. You got to tell a story. And I do think that that is a lost art or it's increasingly so, a lost art. I don't know what kind of, you know, candidate school, some people need to be put through. But I just think there's definitely a rise of the sort of dominant Democratic candidate.
Starting point is 00:56:31 that doesn't know how to reach people on an emotional level. And but also, but to be fair, to be fair, Jesse Jackson was running in the 80s, he was running against those types of like almost technocratic candidates, right? And that's one of the reasons that they lost spectacularly against Ronald Reagan, who was very much not that, who actually was the sort of like, how do you move people kind of figure,
Starting point is 00:57:01 on the right. And so it is such an, to me, it's such an important takeaway from Jesse Jackson's that some of it's a skill. You can't really teach it. But selecting for that in candidates, I think, can be really important because, you know, if you have a candidate who can speak to people, who can understand how to craft an argument that addresses the practical day-to-day needs, economic needs, safety, you know, education, people's futures, you can actually speak to them on that level. That is that should probably should be the price to entry and it's not really anymore. No. And, and you know, I mean, I, in this moment, you have to ask the question, okay, there are probably some Democrats who do this, but the Democratic Party doesn't know what to do with them.
Starting point is 00:57:55 maybe it's you know and that's that's they have to figure that out but I but but one of the one thing I will say is that Jesse Jackson had this base that was so energized it was a lot of young people it was a lot of disaffected voters it was a lot of new voters and he brought them into the political process and then the party was kind of like we don't really need them it just wasn't a priority to sort of bring those people fully into the process, even while he lost the primary into the general election. And I think that is a sort of lesson, right? That it can be a mistake, even if you don't endorse the sort of left-wing politics of a certain candidate. What do you do with their people? Right. What do you do with their people? And the failure to do anything
Starting point is 00:58:49 with Jesse Jackson's people, I think, really hurt Democrats. We've had that. problem over time. But it's also like it's the reason that he has those people is not just because of his issue positions, though that's a big part of it, but it's also because of something unique that he had. And I think that that's part of what we are missing. I mean, just like, and you write about this that, you know, he he campaigned with poor white people and farmers and literally went places where you would not think that Jesse Jackson would go. And his rhetoric, I mean, what I, I went back and read his 1984 speech at the convention, because I was always one of my favorite speeches. It's funny, it made me go back to when I was first in politics and I first loved speeches, I would go to this website, AmericanRetoric.com, and they rank the 100, yeah, yeah, the 100 best speech.
Starting point is 00:59:40 And so I went back there last night because I was looking at Jesse's 1984 speech again. And it's like his speech, Mario Cuomo speech at the convention, Lyndon Johnson's, We Shall Overcome, King, obviously. I have a, like, when you look at those top 10 speeches, they are all speeches that are like powerful, telling a story, like really just like searing in a way, but also like well, like Jesse Jackson for all the, well, he's on the left and the politics and maybe he's radical. Like, he was, he was constructing a pretty persuasive argument and trying to reach people who were not with him. Absolutely. And that's, that's part of the misconception about, about his candidacy was that he spent. a lot of time in places that Democrats don't go anymore. Yeah. You know, he was at Farm Aid with Willie Nelson talking to a sea of white people about
Starting point is 01:00:32 progressive politics. And this is like what, it's like our FK's campaign too. We used to have candidates like that. He was with farmers, between the two campaigns, between 84 and 88, with farmers whose farms are being foreclosed, rallying with them. He was going down to the deep south, back to Selma. and talking to the guy who, you know, 15, 20 years earlier had been on the bridge beating the civil rights protesters.
Starting point is 01:01:00 So he went places that I think even today you don't see a lot of Democratic candidates willing to go to, trying to persuade people who normally wouldn't be inclined to talk to him and actually succeeding in large part. And then those speeches, both the 84 convention speech and the 88 convention speech are very good speeches. They are arguably some of the best ever to be delivered at a political convention. And they also, when you read them,
Starting point is 01:01:30 you're like, oh, yeah, he's talking about hollowed out factory towns and steelworkers who need to go back, get back to work, and how we need to stop being engaged in foreign wars and spend the money on bridges and roads at home. And it's like, wait, who does that sound like? I know, I know.
Starting point is 01:01:45 And that's, I mean, that's not, that's not to say that Jesse Jackson and Donald Trump have anything policy-wise in common, except that they understand that you have to talk to people about their actual lives in really concrete ways and paint a picture for them of their existing life and then the version of it that you're arguing you can change. And I think he really understood that well. And I think Trump understands that really well. That's why, you know, it's been really hard, I think, for Democrats to respond to Trump
Starting point is 01:02:24 because I think he's kind of stolen some of their messaging on some key issues. And figuring out how to get that back is going to be part of the task ahead. It's become such a cliche in politics to, like, meet people where they are. But I kind of want some Democratic candidate to take that literally and, like, launch their presidential campaign by, like, going to West Virginia, going to Mississippi, going to these places that are going to have like no electoral value to a Democratic, to the Democratic nominee. Jesse Jackson was in West Virginia. He was in all those places. And like don't, don't set up an event where it seems like it's all artificial and you have your events. Just like, go.
Starting point is 01:03:04 You know, we're in a national environment. Someone's going to film it anyway. It's going to end up on social media. I mean, Trump did a little of this in 24 where we were like, why is he going to Madison Square Garden? Why is he going here? And part of it was just the message. Bronx. Yeah. Yeah. I think that's exactly right. I mean, Jesse Jackson launched his campaign in 88, in this small Iowa town called Greenville. He had gone there like the year before and was invited by locals and went to this church. And it was like, I think it was like Super Bowl Sunday or something. And a thousand people showed up. And then so he really had a connection to this place. It was literally a small town, a tiny, tiny town.
Starting point is 01:03:48 And there was nothing there. It was so, it's close to Missouri. So then when he announces his campaign, all these farmers from across the border come just to hear him. And it's this kind of like they're in this old, this barn area and they've got people on tractors. And it's that kind of vibe. And here he was, this candidate that everybody was like, well, that's the black candidate. And he doesn't launch in Des Moines. he doesn't launch in one of the bigger Iowa cities.
Starting point is 01:04:16 He goes to the country, like where there are really only white people. And there are a lot of farmers, and there are a lot of people who otherwise have no reason to be interested in his message, and drew a big crowd and launched his campaign there. And that was symbolic, not just for the press, but for himself, because I think he, it was important to him that people saw that he, he, he, he, he, he. envisioned his campaign as encompassing more than just people who looked like him. He really did believe that the message that he had had resonance with those people too, and they did more so than I think people recognize because it just doesn't get remembered. I mean, in the book, there's this great photo that I am obsessed with because it's like Jesse Jackson and he's standing, I think he's on a tractor. And there's like a young boy, like a young white boy in the photo.
Starting point is 01:05:12 standing next to him, but then all these men, farmers, with sacks of brown paper bags on their heads, with their eyes cut out. And they had the sacks on their heads because their farms were being foreclosed on. They were protesting against that. And they were hiding from the people foreclosing their farms. But they wanted to show up at this Jesse Jackson rally. And I tell the story in the book about how he did this rally with them. And then they went to a church down the street. And the farmer sat with the sacks on their heads in the front row and the pews of the church listening to Jesse Jackson give this like stem winder of a speech in a church. And it is, it's the story of this candidate who was so different from everything else that was going on. But I think
Starting point is 01:05:58 part of it was the media environment. There was no internet. So a lot of that never really broke through. You know, I mean, some of those stories. He probably would have done much better in a, Yeah. In an attention environment like we have today. Yeah. I mean, some of those stories were not even reported on. I had, I talked to some people who were there, which is how I was able to write about it. But in the newspapers, it wasn't, people weren't writing articles about Jesse Jackson talking to farmers all that often.
Starting point is 01:06:25 Yeah. And you imagine what would have happened if they did. What a quintessential American scene, though. Just the church and the, I mean, just it's, well, a good version. of an American, in my view. Yeah, I mean, the brown paper sacks could be a lot of different things. A lot of different things, right, yeah. But in that case, it was, it was not.
Starting point is 01:06:46 But it just tells the story of, also, those people, they're just, they were the type of people who their family and friends would have not wanted to see them at a Jesse Jackson rally. Yeah. But they showed up anyway, because he was the only candidate talking to them, the only one. Yeah. Last question, and I'll let you go. How did you find the time to write this book? I think you were like a new mom when you were starting to write it and you still have your day job? I was pregnant with my one and only daughter when I started it.
Starting point is 01:07:23 Yeah. And I just started anchoring my first show inside politics when I started this. So, I mean, bad timing. I will concede. Yeah, I mean, it took a while. It took a while. But I also think, you know, part of it was in writing this book, I kept struggling with, how does the story end? Like, what's the conclusion about today's politics?
Starting point is 01:07:52 And because every four years, right, something massive happens in our politics. You know, in 2020, when I first started writing the book, Biden had won. Then in 2024, Biden loses. Yeah. So, like, where are we going? And I think that's still kind of unclear, but I think one thing that is not unclear is that this fight for the working class American is well underway. And it is, that is the pitched battle that both parties are in right now. And I think that's what this book is about. How do you reach those people? And if you are a Democrat, how do you reach those people while also not abandoning the coalition? of voters that makes up the Democratic Party. And I think that is where there are so many lessons from Jesse Jackson. But I also just, I mean, it's as a writer, sometimes you want to be able to say, well, this is what you do with this information.
Starting point is 01:08:47 I think the answer is actually that it's TBD because we're still in the middle of this very important consequential conversation about the future of economic populism and political populism in this country. Yes. And we have been for several decades. But this is an important part of it of that discussion. Abby, thank you so much for joining. Thanks for having me.
Starting point is 01:09:10 The book is A Dream Deferred Jesse Jackson and the Fight for Black Political Power. It's fantastic. Everyone go pick it up. Thanks. Thank you. Before we go, some quick housekeeping. We get a special deal right now. If you sign up to become a friend of the pod, we're offering an exclusive 20% off when
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