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Scott Galloway
Founder; Host of The Prof G Pod; Co-host of Pivot and Prof G Markets, Prof G Media

Heather Cox Richardson: What History Predicts Happens Next

📅 Jun 18, 2026 The Prof G Pod – Scott Galloway 64 MIN 881532 VIEWS 62 SEGMENTS · 2 SPEAKERS
As the United States approaches its 250th birthday, Scott Galloway speaks with historian Heather Cox Richardson (‪@heathercoxrichardson‬) about the future of American democracy. They explore Trump's politics of spectacle, the war in Iran, the state of both political parties, and what history suggests comes next. Subscribe to Prof G+ to join our next livestream at www.profgmedia.com. Check out Letters from an American ⁠at https://heathercoxrichardson.substack... Timestamps 00:00 - In This Episode 01:15 - Is Trump’s cheating getting worse or are we more aware of it 03:32 - Was renaming the Ke...

Questions asked in this interview

12
  1. 0:00People ask me every day, how can I convince my deeply MAGA uncle to vote for a Democrat?
  2. 0:37It's always a pleasure, Professor Galloway. How are you doing?
  3. 7:35So is it a win in general because he managed to grab it?
  4. 9:50I don't see a good deal coming out of this. What do you think?
  5. 13:23... is the times in which Trump writes at the bottom of his social media posts, 'Thank you for your attention to this matter.' Is that, am I correct that that tends to be associated with dunning somebody for bills that have not been paid?
  6. 15:02Or an attempt to collect a debt, right?
  7. 15:41You know, to what degree do those things speak to each other?
  8. 34:43What do you think about that?
  9. 41:24And you think of even things like The Scarlet Letter, right, which everybody suffered through in high school, is really about that question, you know, to whom are you loyal?
  10. 54:21... of course, but there does seem to be an extraordinary divorce right now between the stock market and the companies that are hot and what the American people actually need and the companies that are providing that. Is that unfair?
  11. 59:08Isn't that by definition that they can peacefully coexist?
  12. 1:00:38This is such a great question, Kristen, because that's the real, you know, when people ask me every day, you know, how can I convince my deeply MAGA uncle to vote for a Democrat?
Heather Cox Richardson 0:00 ↗
People ask me every day, how can I convince my deeply MAGA uncle to vote for a Democrat? And the answer is you can't. The trick to changing society is to mobilize those people who were either soft voters or who didn't get involved previously. That's the way you change American politics: is you talk to your neighbors and not say you're an idiot. You say, 'Hey, are you aware that there is a private prison going in next to our elementary school?' And that's what makes people show up. And it does work.
Scott Galloway 0:35 ↗
Heather, thanks so much for being with us today.
Heather Cox Richardson 0:37 ↗
It's always a pleasure, Professor Galloway. How are you doing?
Scott Galloway 0:40 ↗
You know, I'm doing all right. I guess I'm in a constant state of anxiety. Low, I would call low-level anxiety. How are you feeling?
Heather Cox Richardson 0:53 ↗
Same. You know, and one of the things that really jumps out to me is how many different stories are coming at us from so many different places where you not only have to read what is in front of you, but also guess what is really happening. And that's just a lot of mental work. And you know, you and I devote our lives to it, but for people who are trying to pay half attention, I just don't know how they're getting through their days.
Scott Galloway 1:16 ↗
Yeah. It's sort of which story to focus on and where to allocate your attention and your, not your outrage, but your concern, if you will. So, let's start with something you wrote in the past week, and it's been sort of a masterclass in two of Trump's defining moods: cheating the system and spectacle. The reflecting pool renovation cost 16 million, 10x what he claimed, and is now fouled with green algae. The Kennedy Center tarp is still up. The UFC fight sponsored by his own family's crypto company. In your view, talk a little bit. Is the cheating getting more brazen or are we just more aware and sensitive to it?
Heather Cox Richardson 1:55 ↗
I think probably both. And the fact that we're getting more aware of it is interesting and I'd love to pick that back up. But what the thing that really jumped out to me in the last week was the members of the Kennedy Center board being really clear about the fact that they had fulfilled the court order to take Trump's name off the building, which they may or may not have done. And we assume it's been done because they certified to the court they had done it. But then they covered it with a tarp, obviously now a tarp that's designed to stay there for a long time because they've actually cut pieces through it to access the doors of the Kennedy Center. And that just jumped out to me that literally they said, 'We did what you told us to,' but obviously while they filled the letter of it, they did not fill the spirit of the order. They went ahead and made it sure that people couldn't see that Trump's name was off and they covered up Kennedy's name as well. And it just jumped out to me that this is just such a hallmark of the Trump, you know, family business and certainly Trump himself to always find a workaround, always find a way to cheat the system. And it's not just being a con man, which is something else. It's I am cheating the system. And that to me, I think illuminates not only Trump, but also many of the people who follow him because they're like, 'Yeah, he's just a smart businessman. This is the way you're supposed to do business.' And in a way that's a real denigration and destruction of what the system is, which is the American people trying to make rules under which to govern themselves. So I actually thought that tarp was a really big deal in terms of illuminating the way that Trump thinks.
Scott Galloway 3:33 ↗
Yeah. I wonder sometimes if those of us who follow this stuff, it occupies a decent amount of our bandwidth whereas the majority of Americans are just freaked out about the cost of eggs. You know, is this, it's another example of how weird the guy is. And you know, I felt like when he put his name up, it was the equivalent of spray painting your initials on a monument. You know, I thought I was fairly confident it was going to come off, but does he, do you think he plans this knowing it's eventually going to come off, but it's a distraction from the real work of governance, which is not, you know, where he does not acquit himself well. Is this a purposeful distraction?
Heather Cox Richardson 4:12 ↗
Oh, yeah. You know, I think what is really going on with him, and again, not a psychologist here at all, somebody who studies people in power, I think he can't move backward. He always has to be testing the limits. He always has to find a new way forward. And I remember, you know, back when OJ Simpson was in his white van trying to get away from the cops and talking to a friend who was in LA at the time and saying, 'Oh my god, this is it. This is the end.' And the guy said to me, 'No, you don't understand this kind of a personality. He will never stop moving forward. There is no way for him to say he's sorry to move backward or to try and work within the lines because he's always got to push that envelope until he is stopped.' And I think that's Trump to a T. You know, if you say to him you can't do this, he's going to find a workaround and do it some other way until, you know, the system really does finally stop him.
Scott Galloway 5:03 ↗
I want to put forward a thesis that my co-hosts at Pivot, Kara and Raimondi, have pushed back on and I want to get your response and that is I think that we have a tendency in the media or the people that we, or at least my bubble who I hear from a lot are fairly progressive and have embraced or have not embraced what I'll call a more aspirational vision of masculinity and are interested in it quite frankly. And I love what David Frum said about the border, that if progressives won't enforce the border, fascists will. And when I think about the UFC fight, I actually believe that it was a win for Trump and that is if Democrats can't come up or progressives can't come up with some sort of aspirational form of masculinity around strength and service and, you know, I don't know, absorbing complaints more than you complain, helping others, then Republicans or Trump is happy to fill that void with misogyny and violence. But I would argue that the UFC fight was at a minimum a distraction from Iran and most likely a win for a large portion of his base. What are your thoughts?
Heather Cox Richardson 6:18 ↗
I'm going to disagree with the first and partially agree with the second and that is one of the things that jumps out to me that I find fascinating right now is the degree to which new rising Democrats are embracing the American military. And the Republicans are walking away from the military. They're really treating them, you know, really in sometimes, I think, inadvertently in really poor ways. You know, when Trump kept saying that only losing 13 people in Iran was not that many people, well, you know, it mattered a lot to the 13 people and all their friends and family and the people who recognized the service that that entailed, but also in the ways that they're like undercutting them, the VA, and the many ways in which they are not treating service members well. And the Democrats, in contrast, are supporting them, are stepping up, and are articulating the idea of an American military that not only protects America, but that also contributes to this larger civic body. So, I think that's a really big difference in terms of the way you approach masculinity in that case. Now, in terms of the UFC fight, I agree with you. I think it was designed to be not only a distraction but also an embrace of that kind of violence at the heart of...
Scott Galloway 7:34 ↗
Yeah.
Heather Cox Richardson 7:35 ↗
But is it macho? I mean that's the interesting thing about it that, you know, a lot of, if you look at the number of people who approved of the idea of there being a cage match at the White House, which is different than a sport elsewhere, only about 16% thought it was a good idea to have it at the White House. And that idea that masculinity involves simply beating the crap out of each other, I'm not sure flies with an awful lot of people. So is it a win in general because he managed to grab it? Maybe. But more than that, you know, the fact that it was at the White House. And for me, the real thing about what happened with the UFC match was the fact that they were openly selling branding at the White House, you know, and somebody made the comparison between it and, well, you know, there have been a lot of christenings and, you know, you had, you know, we had to suck that up, you have to suck up the UFC fight. I'm like, 'Yeah, but a christening, I'm, you know, I don't, I'm not really real up on a lot of christenings, but I don't remember them saying, you know, here's an ad, whoever this christening company is.' And that commercialization of not only the White House, but also the United States of America, I think, is deeply off-putting to an awful lot of people who recognize that it's our country and somebody else is cashing in on that. And at the end of the day there's going to be somebody holding the bag and it sure looks increasingly like it's going to be the American taxpayer. And that's something that I think, as you go back to your comment about eggs, you know, I don't think people are real keen on that idea that we seem to be spending money like water while ordinary people can't make rent.
Scott Galloway 9:11 ↗
That's a good segue into what is the kind of dominant story in the news right now and that's Iran. And Trump announced the Iran deal and I think he's taking license with the term deal. It's, as I understand it, a memo of understanding from his birthday cage match, posting that he was fully authorizing the toll-free opening of the Strait of Hormuz and that ships of the world start your engines. National security scholar Tom Nichols wrote that Iran leaves the conflict stronger than before, government intact, now controlled by the RGC, missile stocks preserved. What? Give us, Heather, give us your take on this quote-unquote deal.
Heather Cox Richardson 9:50 ↗
Well, of course, we don't know what's in it. We do know that what is being signed in Geneva on Friday is a memorandum of understanding. That being said, both Iran and the United States have gone in the media and to talk about what they say is in it. It's already being picked up in right-wing media as well as across the spectrum that if in fact it's such a great deal for the United States of America, why aren't they releasing at least the terms as they are understood? And just this morning, JD Vance was sort of backtracking and trying to say that people's criticisms of it were because that was Iranian disinformation. But if that's the case, let's see it. Right. That being said, you know, from the beginning when this conflict that clearly Trump designed to look a great deal like Venezuela, he always even still continues to compare the two. When it didn't work out as he planned, he didn't have a lot of options. And he doesn't have a lot of options now. I mean, Iran has figured out that it can use the Strait of Hormuz for real as leverage and there's not a lot of things that people can do about it. The United States has not turned out looking real good against a mediocre power. It certainly looks as if the United States is a lot weaker than Iran. And you know, coming out of this, and you know, I actually sat around on more than one occasion thinking how does the United States get out of this in a way that ends up with something that looks at least like February 27th, 2026, the day before Trump began the air strikes along with Benjamin Netanyahu of Israel. And you know, I'm not a negotiator for sure, but I did not see a way to come out of this in any way that looked like a win. And I think that's just where he is. And all the criticism, which I think is quite warranted, we shouldn't have gone in there. I don't see a good deal coming out of this. What do you think?
Scott Galloway 11:44 ↗
Well, I go to the term memo of understanding. It's a business term and I've received and I've written several memos of understanding. What they are is typically in an M&A environment where someone gives you a memo of understanding saying, 'All right, Heather, you have a really robust Substack and newsletter business and we'd like to acquire it and this is our understanding of the business, the revenues, mutual NDAs, and this is kind of a valuation range, and now we're going to do the hard work to see if we can get to a deal.' And I would bet somewhere between 30 and 50% of memos of understanding actually result in a deal. And it strikes me that to position this as a deal is disingenuous. It's an agreement to pursue an agreement. So to celebrate seems premature. And my general read of the situation, and I want to get yours, is that every day this is extended without a very, very definitive deal, advantage and leverage is ceded from America to Iran and that they are just playing delay and obfuscation, recognizing the American people have no appetite to go back into Iran. And so memo of understanding, stop bombing us. More and more reticence to get re-engage militarily in Iran and we are going to, the IRGC will if they want have control of the state of Hormuz, start to rebuild and enrich uranium. This to me feels like we have the most expensive boomerang in history and that is we have essentially paid a ton of money and credibility in terms of US brand equity such that we could get a worse deal than we had with the JCPOA. I apologize for the word salad there. Your thoughts?
Heather Cox Richardson 13:23 ↗
I agree with you. I agree with you across the board on that. I do wonder about two things though. One is that if you look at the timing of the announcements of understandings, which have been 39 of them I think at this point, it certainly seems to be designed at least in part to affect the market. And that idea is, you know, again, there's a lot to untangle there, but somebody's making money off this deal and it's not just the Iranians. And that I think is also something to factor in here. But I agree with you, you know, the United States can't withstand the oil pressures the way that the Iranians can right now. And that, you know, if you look at the declining stocks or reserves of oil across the United States, and I thought it was really interesting a few days ago when leaders of some of the major oil companies actually went to the press and said, 'We have told the White House that we're running low on stocks and something has to happen.' I thought it was interesting that they were concerned enough that rather than simply quietly saying it, they actually went to major outlets to make sure the American people saw that. I think you're right. The US, like I say, is, I hate to say it and I'm really sorry, over a barrel. So when you talk about the language of the memorandum of understanding, one of the things that I'm really curious about is the times in which Trump writes at the bottom of his social media posts, 'Thank you for your attention to this matter.' Is that, am I correct that that tends to be associated with dunning somebody for bills that have not been paid? Yeah, that feels like that's really interesting. It does feel like a collection notice.
Scott Galloway 15:00 ↗
That's the word I'm looking for.
Heather Cox Richardson 15:02 ↗
Yeah. Or an attempt to collect a debt, right?
Scott Galloway 15:05 ↗
Well, I'll put forward another thesis that when you value fealty over competence, these agreements have nothing to do typically with the leaders of the IRGC and the president. These agreements have to do with 150 to 250 well-trained, deep, experienced diplomats of which we have gutted our diplomatic corps. And the level of incompetence or opting for fealty over competence is bubbling up with agreements that are built on very tenuous sands that ultimately I don't believe this is going to result in anything close to an enforceable agreement. Your thoughts?
Heather Cox Richardson 15:41 ↗
So my thoughts are that this raises the next question. I agree with you by the way. I think that he's, like I say, that I don't see a clean way out. And you know, you've seen this. He says there's an agreement, issues things within it leak. There's an outcry, especially from the right, outcry, and then he backs off and he blows the whole thing up. And I don't see any reason to think that this should be different except for that pressure of the rising prices that are going to be hitting with the reduction of oil stocks. But it does raise a larger question, I think, about where the United States is in this moment. And that is obviously this is hitting consumers incredibly hard. They were already hurting from the tariffs. Now they're going to be hurting even more from the rising cost of diesel and the cost of what that's going to do to food and gasoline and so on. But to what degree is the corruption and the incompetence and the self-dealing among Trump and his inner circle affecting the way that ordinary Americans who are not paying a lot of attention to that because they're working three jobs to put food on the table? You know, to what degree do those things speak to each other? And I have an idea about that, but I'd love to hear what you have to say about it.
Scott Galloway 16:58 ↗
This is your trick. You asked me what I think.
Heather Cox Richardson 17:00 ↗
Oh, well, you know, but this is the problem because I know what I think and that's not very interesting. So, I'm always interested. I think it's a lot more interesting than what I think.
Scott Galloway 17:07 ↗
But as someone who loves to hear the sound of their own voice, so I'll answer. I think in America it has become a national pastime of being critical of our government. And I would argue our government is the best performing organization in history. And I think we have just taken for granted at every level how thoughtful and credentialed people in the CDC are and the diplomats who try and hammer out and cross the T's and dot the I's of an incredibly complex deal like this. And that we have essentially gutted and neutered the competence of the best organization in the world and Americans have taken for granted believing that these things just operate on some sort of autopilot. And I think we're about to figure out in a very painful way that no, there were very smart people working at the TSA. There were very smart people working in the IRS, the CDC. Those people were there for a reason. And when we decide to take out our entire Iranian diplomatic corps, staff our intelligence agencies and our security apparatus with loyalists as opposed to people who have any background, that eventually you end up with poor execution. And I think a lot of this is our fault. I think a lot of Americans have taken for granted the commitment and expertise that is resident in our government. And I think that those chickens are coming home to roost.
Heather Cox Richardson 18:31 ↗
I agree with you. The question is whether or not people are going to recognize that. And I would say a couple of things about it if you wanted to hear stuff coming out of my head on this. The first is that one of the things that really has jumped out to me lately in the last week or so, so maybe it's fleeting, is what happened after the great crash in '29. Was that if you think about the '20s, there were times in which the production increased dramatically but the benefits of that really stayed in a very small group of people. And yet the popular imagery of that time, especially coming out of World War I with all of its advertising, for example, and all that new technology, was one in which people who read the popular magazines and paid attention to the radio and did all those sort of newfangled things thought that the world, the United States, was really this incredibly prosperous place. And they didn't pay a lot of attention to farmers and to wage workers and to marginalized Americans, especially racial minorities, saying, 'Hey, things aren't so great over here.' But what happened after '29 was that with that crash, when the entire economic facade just came tumbling down, all of a sudden, Americans, especially white Americans, who had previously disagreed with the idea that there was anything wrong with the economy, started to look at their former bank accounts and started to look at the people who had ripped them off. And their fury at that point was overwhelming. And that's how we go from the '28 election, which is a landslide for Hoover, to the '32 election, which is a landslide for FDR. And I wonder, you know, there was a story that came out the other day about how when he was governor of Ohio, John Kasich had done this deal with tech companies absolving them from a need to contribute to Ohio state taxes for I think it was up to 40 years so long as they met certain standards. And you know, it didn't really make a lot of waves until all of a sudden people are now discovering it with the advent of data centers and they're outraged. And that just seemed to me like that sort of backward look that looked a lot like the backward look of the early 1930s before FDR comes in when people are so mad at the head of the stock exchange and people like around Hoover and Mellon and so on that they decide that when Herbert Hoover walks down the street, flowers die when he walks by. And I wonder if maybe we are going to see as this economy gets more and more stringent a furious look back at how we got here over the past couple of decades.
Scott Galloway 21:19 ↗
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The word I keep returning to is there needs to be a reckoning. And just as, so for example in '29, my understanding is the policy response was exactly wrong. They tightened the purse strings thinking that they needed fiscal discipline when they absolutely should have flooded the market with stimulus. And if you look at '08, you have to, in my opinion, give credit to the Fed chair and banks and the central bank for a response that was overwhelming. Everyone talks about, catastrophizes about AI. We've been to this movie before. There was a 25% destruction in labor in the first few months of COVID and the response was swift and some people argue we overdid it, but Janet Yellen said the risk of underdoing it was much greater than overdoing it. And the government response, I would argue, was outstanding in terms of the economy. We never really had a full recession. I would hope that what we're seeing now on a lot of levels would inspire a reckoning. The issue is whether or not the incumbents or the Republican party is able to frame the primary signal of prosperity as the stock market versus affordability or inflation or generally how people feel that they're doing. But that brings up a question in that as you brought up a reference to the late '20s in terms of Trump's foreign approach to foreign policy. What is the analog in terms of another president or leadership in terms of a similar approach? And also you reference this time maybe being somewhat like the late '20s. Are there other periods you can look at domestically in our history that feel very 2026?

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APA

Galloway, S. (2026, June 18). Heather Cox Richardson: What History Predicts Happens Next [Interview transcript]. The Prof G Pod – Scott Galloway. CEOInterviews.AI. https://ceointerviews.ai/interview/3002636/

MLA

Scott Galloway. "Heather Cox Richardson: What History Predicts Happens Next." The Prof G Pod – Scott Galloway, 18 Jun. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3002636/.

BibTeX
@misc{galloway2026_3002636,
  author       = {Scott Galloway},
  title        = {Heather Cox Richardson: What History Predicts Happens Next},
  howpublished = {Interview transcript, The Prof G Pod – Scott Galloway. CEOInterviews.AI},
  year         = {2026},
  month        = {jun},
  url          = {https://ceointerviews.ai/interview/3002636/},
  note         = {Speaker-attributed transcript with timestamps}
}