I’ve got a story to tell you. A populist candidate fuels a presidential campaign by railing against political elites, appealing to white grievance and whipping up the emotions of large crowds with his candor and lack of political correctness. Sound familiar? Or how about this one: A businessman who once identified as a Democrat sweeps to the GOP presidential nomination despite never having held elected office. And this: A billionaire gains traction railing against Washington and foreign trade agreements. Of course I’m talking about Donald John Trump. But I’m also referring to Alabama Governor George Wallace, who ran a strong third-party campaign in 1968. And in the second instance, I’m talking about Wendell Willkie, the Indiana non-politician who surprisingly topped the Republican ticket against Franklin Roosevelt in 1940. And, finally, Ross Perot’s failed run in 1992.

It’s easy to think we’re living through an unprecedented campaign season as we watch the Trump train careen off the rails. Yes, elements of this election are totally bonkers, as if penned by a dystopian novelist writing a biting satire of our political process. But even through the haze of crazy, there are echoes of past elections that can actually help us understand the dynamics at play in this campaign.

But I’d be lying if I told you I made these connections to the past on my own. To help put this election in context I’ve relied greatly on John Dickerson, a columnist at Slate and moderator of CBS’s Face the Nation. For more than a year, Dickerson has hosted the podcast Whistlestop, where he delves into of the most indelible and influential moments in American presidential campaign history. He tells the stories of “The Dean Scream,” “Reagan’s Nashua Moment,” John McCain’s “Straight Talk Express” and many more tales of elections past. In each episode he takes care to help the listener understand why these events were so pivotal.

This month Dickerson released a book of the same name, expanding on what he’s done with the podcast. I met up with him to discuss his book, Trump, racism, the rise of the conservative movement and what—if anything—campaigns actually tell us.

Twelve Books

Twelve Books

Did learning the history of American elections act as an antidote to our hyperbole of today or did it prove the current race is unprecedented and crazy?
It’s kind of both. Sometimes when you look at the Whig campaign in 1840, the Whig parade in Columbus is basically eight hours of drunken revelry. That’s a total circus, so in that sense, today’s craziness is still actually less crazy. So on the one hand, it’s like, “Wow, it was really out of control back then.”

I also learned about Jefferson, Adams and Hamilton and how viciously they attacked each other through editors in the newspapers. I hadn’t realized what an active role Jefferson played in paying for the journalists who savaged the Federalists in the most despicable of terms, and spread all kind of stories that weren’t true. In some cases, they were exactly true, which was what undid Hamilton.

The past was crazier, but then there were parts of the past where it was much more edifying and sort of praiseworthy campaigns. Some of the debates during the Republican primary in 2000 and during the Democratic primary debate in 2008 were real policy debates. They would get hot every now and then, but they were substantive debates about stuff. It was amazing compared to what we have now.

What are the antecedents you found to this campaign in American history?
There are more historical antecedents than people might think. When people started talking about the connections between [former Alabama Governor and 1968 Presidential Candidate George] Wallace and Trump, then I was going to really learn about what connections were real and what connections don’t exist.

When you look at Wallace, a lot of times you think you’re reading the same stuff Trump says when you hear him talk about elites and the disappointment and disaffection people feel, and journalists writing about how he tapped into a certain kind of anger and disaffection in the electorate. And also, when he talks about protesters at his rallies and feeds off of them. The same way Donald Trump raises money off of protestors that interrupt his rallies, George Wallace and his aides said if they didn’t get protestors at his rallies, they’d hire them because his protestors loved it when he got into back-and-forth with protestors.

That sounds like when Trump senses his crowd’s energy is low, he tells them he’s going to build a wall.
It’s stoking the passions. Wallace was considered a joke in the beginning the way Trump was. Now Trump got a lot further than Wallace did. Wallace was able to get on the ballot in all 50 states, which was a serious political achievement. But, it wasn’t as big of a deal as getting the nomination of a major party which Trump has now done.

Were both Wallace and Trump’s supporters stoked by a white working-class resentment?
One of the struggles I’ve had because I didn’t live in the time of Wallace—I was a week old—is discerning the motivations of the people who are on the Wallace bus and on the Trump bus. Clearly some people on the front row basically don’t like immigrants because of their race. But, the people on fourth and fifth row of the bus are worried about the economy and think maybe a businessman can get it done, and they think immigration is a problem, but they’re not racist.

Anderson Auction

Anderson Auction

They have economic concerns that he speaks to, but they’re all on the same bus and what some people would say—and I don’t go this far—if you’re on the bus at all, then you have an obligation to call out the people who are on it. It should be unconscionable that a white supremacist can be supporting Donald Trump, and that should be reason enough to leave. That’s what some people would argue. There’s obviously a racial element to what Wallace did and what Trump has done. The challenge for anybody covering it is how much of it is that, and how much of it is a lot of other things. There are clearly other things too, but Wallace was obviously a straight-up segregationist, so it was obviously much more the case in Wallace’s time.

I think what’s highlighted the campaign for me is there’s almost two different thresholds of racism. One group’s definition of racism requires overt expression to qualify. I think a lot of the progressive left now would say racism is actually an indifference to the discrepancies of race. That’s an important distinction because maybe we’re not even speaking the same language when I say “that’s racist,” and the person I say that to can claim that doesn’t fit their definition of racist.
So there’s implicit racism and explicit racism and then there’s what you’re defining, which is a third thing: racism by omission. That argues you should be more actively concerned about the disparities in the culture and in the economy, and if you’re not, that’s a kind of racism. That’s a fascinating dispute that’s on the further edge of things. The problem with that is when you use the same word to describe that whole range, it’s a mess because then when something truly racist happens, the word kind of lost its meaning, and then it’s hard to give it its proper name, and tell people, “Look, this really is beyond the pale.”

Well, when people are unsure whether to call something racist they say, “that’s problematic.”
When Paul Ryan said that Trump claiming that the judge’s race would be an impediment to fairly judging his case, like Paul Ryan said, that’s like the textbook definition of racism. That was a big deal when he said that. Boom. But loose use of the word racism would’ve made that less powerful. You already see it; a lot of conservatives think the word is being thrown around all the time, and so for them it loses its punch. When Paul Ryan uses it, it still has its punch, so that’s one of the things we’re working out in this campaign is how to talk about race now in America, because clearly the conversation hasn’t taken place in a way that’s big and broad. Both with dealing with community and policing and the kind of thing you’re talking about, people recognizing disparities that they might not have paid attention before.

Did writing this book change how you cover this election?
A lot, both about what is influencing certain events, but also when in how I describe it. Thinking about the election in historical terms can get you away from the nitty gritty of some silly back and forth and think what’s going to live on past this week. So, it’s been tremendously helpful and also analogies you can draw out, candidates using some of the precedent in the past when Bernie Sanders was making up his mind about what to do in the Democratic convention, I was constantly thinking about Teddy Kennedy and Jimmy Carter, and also what Kennedy tried to do when he was in Sanders’ place, and why Sanders couldn’t do the same thing.

Was there something that was revealed to you, or something that was pretty surprising when you were looking back that you didn’t expect to find out?
The story of Truman in ‘48 is the story of him grinding it out in the campaign trail, but it’s also the story of him having the first state of the art research operation in DuPont Circle providing him with news and information about every little town he would stop in. So, when he would stop, he would say, “Oh, it’s great to be in Pocatello, and I heard you had a great pie eating contest yesterday.” And everybody would be amazed he would know about little ol’ Pocatello. “Boy, he must be just like us.”

Hulton Archive / Getty Images 

Hulton Archive / Getty Images 

That’s the campaign where the title of your book came from, because “whistlestop” was a derogatory term that Truman turned on its head.
Yes. Taft said, “Well, Truman is going off on his whistle stop tour,” and Truman could take umbrage on behalf of the people in little towns who said, “How dare you call us a mere whistle stop. We are a thriving metropolis of 98,000 people!” But, that’s right he would’ve turned anything on its head by attacking the Republican Congress of ‘46 and ’48. That was a big gift to him from senator Taft.

You read so much about campaigns in the past, how does it feel to now be a participant in history?
I’m really happy to be a participant, but I’d rather have people remember what the candidates do and their responses to questions we raise. I don’t know if people remarked about this at the time because I was moderating the Republican debate one night and then I had to do Face the Nation the next day in South Carolina, and right after the debate I had to interview Donald Trump, so it was like chaos, but Donald Trump, standing five feet away from Jeb Bush, said that his brother lied the country into the Iraq war and should be impeached.

That’s an extraordinary thing, and his brother had just been brought out to South Carolina to campaign and his brother had won South Carolina. It was where he came back against McCain. There were all these Bush ties in South Carolina, and Trump said that the last two term Republican president lied the country into war. That’s the position of the super-far left. There have been a lot of crazy things in this campaign, but that’s kind of extraordinary and then Trump went on to win the Republican nomination in the state. Anyway, so that was a moment where I asked a question, you know, so I was a part of the moment in that regard. But for me, the moment is what the candidates were doing to each other in the back-and-forth.

I’m thinking about the Cruz moment about Obama appointing a Supreme Court justice where you almost had your historian cap on there for a second. You challenged the facts of Cruz claiming an Obama appointment would be unprecedented. Maybe being a student of history helps you in your current coverage because it’s harder to make an argument of precedent that’s not fully true.
Exactly. Scalia had died two hours beforehand and what happened with Senator Cruz was just I was still in the mode I’ve been in backstage trying to figure out what is the precedent, and what’s the difference between putting somebody up for nomination and then actually having them go to the Senate. When’s that timeline and which presidents have done it when, so when Sen. Cruz asserted something, I wasn’t necessarily trying to show him he was wrong, I was still in the mode of, “Well, wait which is it?” I was still trying to figure it out myself.

You’ve long been interested in the conservative movement’s rise and evolution, so how has this party gone from a party of elites like Rockefeller, to its current anti-elitist outlook?
Well, you know it’s different factions of the party. Goldwater was fighting against the East Coast elites and representatives of that more populist part of the Republican party in ‘64. And that’s what Trump represents, which is crazy because obviously Trump is an elite, so I think the splits were there. What Reagan did that was so genius was being able to weld those two together and what Trump is breaking. Reagan’s genius was he didn’t leave the party in ’76, and he was able to build a coalition. Coalitions by their nature are fractious because there are people who have different interests, so the great politicians keep everyone roughly happy, and keeps them in the tent. Trump is basically kicking some people from the tent or isn’t going to worry about the fact they’re leaving and is just trying to build the tent with kind of one person.

So, that split has always been there in Republican politics. It has been interesting to watch it shift geographically and temperamentally from ‘52 to today. The party is in a real crisis now. What it means to be a conservative, there’s kind of a time for choosing again, which is a phrase Reagan used in 1964. it’s now Republicans are in a situation where Susan Collins is choosing “no” by not voting for Trump and George P. Bush is choosing “yes” [by supporting Trump], and those will be indelible choices that people will make about where they stand relative to Trump.

Was Cruz trying to have a “time for choosing moment” speech at the convention?
Sort of, but he did it neither fish or foul. His speech has some parallels to what Teddy Kennedy did in 1980. Teddy Kennedy just said, “I congratulate President Carter on his victory here tonight, and then went off and gave his speech about liberalism and Cruz said, “I congratulate Donald Trump,” and then said his speech about conservatism. It’s funny, Kennedy’s speech was considered the greatest of his career and was replayed at future conventions. It was so prescient.

Chip Somodevilla  / Getty Images 

Chip Somodevilla  / Getty Images 

Ted Cruz didn’t even have a Teddy Kennedy moment.
No, he didn’t. He had a Nelson Rockefeller moment where they booed him and even arguably Nelson Rockefeller was more remembered than Cruz. I guess “vote your conscious” might live on from that speech, but what else in the speech lives on? I mean, maybe we go back and look at it maybe it’ll seem incredibly wise sometime down the road.

What’s the future of the conservative movement?
I don’t know where we’re going to have to see what happens. It depends if Trump wins or loses, but there will be a split between the populist wing of the party and the conservative—not establishment because Ted Cruz is in it, and Ted Cruz isn’t a creature of the establishment, really—so I don’t know. Those who want to burn the place down and those who want to operate within a party.

Will we have to worry about overreading the results of this election? Because back in 2004, pundits said Americans don’t care about economic interests anymore, and in 2008, they said the Republican party is dead.
It’s always good to bet on the health of a party the minute it’s being claimed it’s doomed. I mean, in ‘94 the Republicans took over the Congress, in ’96 Bob Dole lost. So yeah, we can overblow the moment, although the Republican party is going through some serious stuff here. I guess my point is, it’s not fatal to the party if they lose and if there’s this crack in it. You can argue it’s healthy for the party, and parties have to do this because what happens is it surfaces an underlying tension. So, if you don’t surface those things and deal with them and talk about them, and get candidates to fight about them, you never actually work it out, and so it ultimately ends up blowing up.

This reminds me of a debate you and David Plotz had back during the Romney primary where he argued “Romney is going to win, why are journalists dragging this out?” And you argued, “Well, it’s interesting that there are so many people still dissatisfied with him being the nominee, so it’s still revealing something to us even if we know the exact outcome.” Now we see that unrest in the party even more intensified.
I’d forgotten about that debate. But that’s exactly right. We don’t stop football games just because one team is ahead. There’s something in the game itself that’s interesting. In this case it’s not a game, but there’s something in the race itself which in that case was disappointment with Romney, but also it’s still people who want to be leaders in the party, going out talking about what they want to lead about, which is interesting.

I mean that’s what campaigns are supposed to be about. So there’s a mistake in that argument David and others make, which is that just because you cover a race doesn’t mean you think the race is up for grabs. There’s a contest going on and its interesting on its own terms and even if Romney has got it locked up, the contest continues and can still tell us lots of things. It can tell us lots other than who’s going to win or lose.

That was [Washington Post reporter] Dave Weigel’s contention with data journalists during the rise of Trump last year. Essentially, you can’t dismiss just because you don’t think he’s going to win, there’s enough happening here that you need to figure out what’s happening.
Dave is super good at that. He goes off and figures out stuff well before anybody. But what’s interesting is that Weigel knows the grassroots better than anybody, and I don’t want to speak for anybody, it’s just even people who know the Republican grassroots still didn’t see Trump coming.

What do you think campaigns actually tell us?
They’re a psychological test of a person’s temperament, which is not unimportant for the office. I don’t think it tells us anything about how they’ll do in office. It’ll tell us whether they’ll crack up in office or have the mettle to deal with it, because campaigns are so weird and unpredictable, and so is the presidency. Campaigns don’t tell us much about a candidate’s ability to delegate, their ability to transfer their will to their subordinates, their ability to set a vision and stick to it, their ability to adapt, or their ability to take risk. It tells us a little about that stuff, but a lot of times the campaign overvalues attributes like communication. As a president, obviously it’s important to communicate, but we’ve gotten a view of the presidency where communicating is everything. That’s not the case. That’s not the way the presidency works.

The question then is could you create a campaign that would tell us something about the candidates, and their abilities in office, and I don’t know how easy that would be, that would be pretty hard to do. I believe a little more now that campaigns do tell us something than I used to, but that’s because I used to believe they told us nothing at all. So, I kind of slightly improved my views on campaigns, which is funny because campaigns have gotten weirder and less useful, but I think as weird as they are that we are living in weird times so that’s a bit of a test of what it would be like to be president.

Jeremy Repanich is a Senior Editor at Playboy. Follow him on Twitter @racefortheprize.