Never has there been a presidential race as sprawling and wide-open as the 2020 Democratic primary. It would be a landscape entirely without a map, except that a small handful of battle-hardened veterans have navigated similar terrain before.

At the kickoff of the primary debate season four years ago, no fewer than 16 candidates were jockeying for position in the largest Republican presidential field in history—only to end up being mowed down by Donald J. Trump in what became a slaughterhouse of a campaign.

What’s in store for this year’s Democrats? To get an insider’s view, POLITICO Magazine invited four of the Republican strategists who managed those 2016 campaigns to a literal smoke-filled room in Washington to talk shop: Danny Diaz (Jeb Bush), Beth Hansen (John Kasich), Jeff Roe (Ted Cruz) and Terry Sullivan (Marco Rubio).

Over drinks and cigars at the Civil Cigar Lounge, they unloaded about the difficulties of breaking through in a massive field, gossiped about the strengths and weaknesses of this Democratic crop, aired old grievances still lingering from 2016 and offered some tactical advice for how to face off against President Trump.

The conversation below has been edited for length and clarity. Check out the audio in the newest edition of POLITICO’s Off Message podcast.

On Debates and Campaign Strategy

Tim Alberta: Here we are, heading into the first Democratic debates of the 2020 cycle. Four years ago, all of you were walking into Quicken Loans Arena for the first Republican presidential debate of the last campaign. What are your most vivid memories from that night? And what were your strategies going in?

Terry Sullivan: We were trying to walk this fine line because, up until that point, we were very much seen as the candidate who could give inspirational speeches and was expected to shine at the debates. But at the same time, our campaign strategy, for better or worse, was to try to fly as much beneath the radar as humanly possible. To not put a huge bull’s-eye on us. To not run out there on Day One and become the front-runner. Also, we sure as heck didn’t have the resources financially to become a front-runner. So, what was running through your head is—do well, meet expectations, do not beat expectations and don’t break away. It was kind of a weird way to walk into it, but we weren’t looking for a breakaway moment; we were looking to check the box, keep our head down and keep moving.

Jeff Roe: I think, at this stage of their campaign, maybe somebody will have a moment against Biden. They’d be smart to do that. He’s starting to drop. If they want to bring him all the way down, they ought to. But in our campaign, we called it “rubbing paint.” You know, a NASCAR reference—kind of trade a little paint in the corners. That wasn’t our game. We were playing golf at that time: right down the fairway, play your own game. There was no Greco-Roman wrestling. You had 7½ minutes of actually speaking, so be a strong conservative and just play your game and try not to make any mistakes. Remember, we almost didn’t make the debate stage. And if we had gotten relegated to the second debate, Ted was going to drop out.

Tim Alberta: Going into these first Democratic debates, who do you all think has the most pressure on them?

Terry Sullivan: I think there are two. It’s Mayor Pete, whose last name I can’t pronounce, and it’s Beto. Because those two are the most a creation of the media, the D.C. media. And so, if they can’t meet expectations, it’s the end of them. Whereas Biden could totally crap the bed, but he’s still going to make [future] debates.

Beth Hansen: I completely agree with that, and I might put somebody like Kamala Harris in there. These are people who voters don’t know a lot about. People know something about Biden; they know something about Sanders; they think they know something about Warren. They know something about those people. It’s these other people where it’s, “Oh, I think I like that person. Let me see.” Those are the people who are going to have to come out and make that first impression.

Danny Diaz: I think it’s the people who are worried about making it through the summer and being on the stage in the fall. It’s pretty clear that Sanders is going to be on the stage, and it’s pretty clear that Biden is going to be on the stage. I think if you’re Kamala or Warren, you’ve got to be like a really good rebounder in a basketball game. You’ve got to hang around the hoop, and you’ve got to get rebounds. I think [for] the folks that aren’t going to make the stage in September … they need to change the game for themselves so that they’re viable. They’re hoping just to make it until the early states [begin voting], and then it’s a totally different game.

Terry Sullivan: It’s an expectations game more than anything else. At the end of the day, perfect example, we finished third in Iowa.

Jeff Roe / Danny Diaz: [Loud and indiscernible mocking of Sullivan, whose campaign famously took a victory lap after Rubio’s third-place showing in Iowa.]

Terry Sullivan: Hold on, though! It wasn’t an accident that we finished third in Iowa, and we got a ridiculous amount of press. We got more press than the first or second did. The point is that it was about expectations.

Beth Hansen: It always is.

Jeff Roe: I hate to agree with Terry, but I owe him one. If Robert Francis [Beto O’Rourke’s given name] has a bad night, that’s real bad. It reinforces the trend line where he starts at 11 and he ends up at 4. He’s at 2 nationally. He has to fix it. Mayor Pete, same thing. Reinforce his trend line up. He’s going from nothing to 13 in Iowa, I think it was an 8 nationally. But I think there’s another contingent, which I think, as you were describing, [is] Kamala. She’s kind of the best political athlete in the field. She seems to have the diversity of being able to speak to donors, be able to speak to the press, be able to speak to grassroots. She’s got a core competency around an issue. She has experience. All of us had great candidates, but Marco was the best natural political athlete in the field. I think he had a lot to prove—

Terry Sullivan: So, you’re saying it’s my fault we lost?

Everyone: [Indiscernible shouting, finger-pointing.]

Beth Hansen: As we sit here talking about the debates, talking about the process of the debates, taking a step back: At the end of the day, is this the best way? I’m not saying I have a better idea, but my God, are the debates really the best way? Those debates with 11 people on the stage? Were they really a good way to indicate who is going to be a good leader of this country?

On the Democratic Contenders

Tim Alberta: Is there a comparison that any of you see at this early stage for your candidates in this 2020 field? Somebody who you look at and you say, “Boy, they sort of remind me a little bit of the candidate I had and the sort of campaign we were running”?

Beth Hansen: I’m going to have to take a minute to think of that because it does not come to mind. Because what we had was experience, and not only at the state level, the popular governor of a big, diverse state; we had 18 years of congressional experience. And at the end of the day, [Kasich] was a Midwestern populist and he was a good communicator and that was the package we had, and I don’t see that in a Democrat.

Terry Sullivan: The better question might be how do we see each other’s candidates? Because [all] of us are going to say our candidate was unique and special. I can say, “John Kasich is Elizabeth Warren. Has zero chance of winning and 100% chance of spoiling another candidate.”

Tim Alberta: OK, that’s a better game. I already made the Biden-Bush comparison, Danny. What do you think? Are any of these folks reminding you of anyone?

Danny Diaz: That’s easy for me quite obviously because he wears the weight of being the front-runner out of the gate. I do notice [that] Warren has placed a premium on policy and ideas at least thus far in her effort, and we played to our candidate’s strength, which was ideas and policies and experience. And I see her doing that once again, with the caveat that [Bush and Warren] couldn’t be more different.

Tim Alberta: What do you think, Jeff?

Jeff Roe: I’ve got Jeb and Joe, Cruz-Sanders, Kasich-Bullock, Rubio-Harris.

Tim Alberta: Wait, Kasich-Bullock? Walk us through that.

Jeff Roe: So, he’s just like a genteel governor who talked a lot about being governor. Bullock’s talking a lot about being governor. It used to be the path to salvation to be president is you’re a governor, not a senator. He’s a moderate, and he’s going to try this kind of statesman route, which there’s not a lot of oxygen for outside your own state.

Tim Alberta: Jeff, you talked about Kamala Harris, in your opinion, being the best political athlete in the field. My question to you all is, regardless of whether they’re underperforming or overperforming at this point in the race, whose campaign would you want to manage just based on raw political talent?

Beth Hansen: Possibly Kamala Harris.

Danny Diaz: I’m conflicted in the answer for this reason: I think the mayor thus far has vastly exceeded expectations. I question the durability of that and—

Beth Hansen: I was going to say the same—

Danny Diaz: It’s very hard for me not to answer the question with [Sanders], the person who took the Clinton operation to two minutes left in the fourth quarter. He has the organization built-in. He has the message built-in. He has the money built-in. He has kind of a lot of energy on his side, and these are people who believe they were jilted, and he has a strong, strong message. Superdelegates and the establishment running the process and whatnot—he can push that button, push it with a high degree of frequency and yield a response that is favorable to his side.

Tim Alberta: What do you say, Terry? You already had the best athlete in ’16 and Jeff says you screwed it up.

Terry Sullivan: The two that are exceptional candidates aren’t going to surprise you: Joe Biden and Kamala Harris. The knock on Joe Biden is that he’s an old guy and he says stupid things. But this general election is genetically engineered for Joe Biden, because he won’t be the oldest guy, and no way in hell is he saying the stupidest things. Donald Trump is a match made in heaven for him. [Biden’s] a good politician, and he’s designed for this race. He appeals to that disenfranchised Archie Bunker. He can win those back from Trump. The person I think is going to surprise everybody is Cory Booker. Not out of anything he’s done so far, but he’s a damn good candidate back to when he was mayor of Newark. The media may move on because he doesn’t seem as sexy at the moment, but I think he might have some ability to really kick it into next gear. And I think Kamala Harris is going to go the distance. The African American community is the single biggest bloc in the Democratic nominating process, full stop.

Tim Alberta: Especially by virtue of the new primary calendar, the way that it’s organized—

Terry Sullivan: I mean, just raw vote totals. It matters. And so, the question becomes can Biden wrestle enough African American votes away from Kamala, or does she win it by overperforming with African Americans but also doing really well with the rest of—

Danny Diaz: As of today, he’s doing it in South Carolina.

Terry Sullivan: That’s what I’m saying. That’s why I put him as the best candidate. They figured it out. Biden knows that basically his nomination largely depends on his ability to communicate with African American voters, specifically in the South.

Tim Alberta: Let’s talk about Biden a little bit. He’s treated in some quarters of the Democratic Party as a front-runner, if not a prohibitive front-runner, for some of the reasons that you all were mentioning: The combination of name ID, big donor support and establishment backing casts a shadow over the rest of the field. But the doubts come into play when we get to this discussion about whether he’s in step with today’s Democratic Party. Danny, you faced a similar situation with Jeb Bush. When you look at the Biden campaign—his handling of the Hyde Amendment, for instance—what is your advice to them? What warning would you give the Biden campaign, so they don’t suffer the fate of Jeb Bush four years ago?

Danny Diaz: You have to have a theory of the race, and you have to pursue it. And from his standpoint, he’s wearing the colors of the front-runner. He’s on a stage with nine other people. There’s one commonality among those nine, and it’s bringing him down. And he’s got to navigate that. But what does he have working for him? He has working for him, once again, March 3 [Super Tuesday]. You’ve got, what is it, like 13 states? Half of the delegates are almost decided in Texas and California alone, and he can run a big campaign. He can run a well-financed campaign. He’s got a pretty good foil in the president of the United States, and he understands that. So, he needs to maintain continuity. That’s his goal, and the longer he maintains continuity, the more of the doubters he brings into the fold. What works against him is he’s been around forever. He has said things, voted on things and done things that he doesn’t recollect, and all of those are going to come to bear.

Terry Sullivan: He’s a 747 that’s tough to get off the ground, but once it gets off the runway and clears the trees, it’s tough to bring it down.

Beth Hansen: And that will be key for him. You say continuity, and I say it’s almost remaining presidential. Just stay above—to the extent that you can—stay above the rest of that fray and not get dragged into it. That is his winning ticket, and the fact that he is the most likely to be able to defeat Trump next November.

Jeff Roe: So, I didn’t get to answer the first one, whose campaign I’d like to run.

Tim Alberta: Well, I assumed that because Kamala Harris is the best athlete…

Jeff Roe: She is, but I’d like to do Sanders. First of all, Kamala is going to be on the ticket no matter what—

Terry Sullivan: Because Sanders is just as crazy as Ted. [Hooting and heckling]

Jeff Roe: Kamala is going to be on the ticket, so that would be kind of fun. But Sanders is being undervalued. He’s an undervalued stock. It could be a lot of fun. And I think I could actually—I don’t know. He might be as bad as they say he is as a person, but Biden can only underperform. I think Biden is really overvalued as a front-runner. I feel like his ceiling, which he just reset at the highest poll, is at 41. He can’t get 41, so he can really only underperform. I think his floor-ceiling is a real problem for him, whereas with Sanders, he’s probably got a ceiling of 35 and a floor of 25. I also think that Biden is really playing out his hand poorly. He’s running a Rose Garden strategy. I would actually saturate and try and be their [version of] Trump in this race. When he does a gaggle, when he does the pizza parlor, when he does whatever, it’s him. I don’t think Rose Garden is going to work for Biden. I think I’d saturate and suck up all of the oxygen. I think he’s more Trump than anybody else they have for the earned media impressions.

Terry Sullivan: Yeah, it’s all about earned media impressions, period. When we measured and I’m sure other guys did and gals did here, but we measured the impressions on the target universe in our analytics every single week for the life of the campaign that we were in it, and from the day that Trump went down that escalator to the day that we stopped measuring when we dropped out, he had more earned media impressions every single week than every other candidate earned and paid media combined, except for two weeks.

Tim Alberta: Was one of those weeks when Marco accused him of having small hands?

Terry Sullivan: No, no, no, because we were talking about him, No. 1. No. 2, everybody asks, “Oh, what was the week?” Nobody knows. He was playing golf. It wasn’t because anybody else did anything smart. It was that—

Tim Alberta: Trump took a little breather.

Terry Sullivan: Yeah, he took a breather. It had nothing to do with anything else.  

On the DNC Primary Rules

Tim Alberta: The Democratic National Committee is fighting a war that many felt was lost by the RNC back in 2016, about how to manage a primary field with a historic number of candidates. You four were running campaigns in a field of 17; the Democrats have even more this time around. Are these new DNC rules governing the debates and superdelegates going to be effective? Or do you expect unintended consequences?

Danny Diaz: I do think the qualifications are the big difference between ’16 and ’20, and I think ultimately it’s pretty clear that after the two summer debates, once they get to the fall, they’re going to narrow the [number] of the folks on the stage—and narrow it substantially. So, based on the qualifications that they’ve delineated, what’s going to be interesting here in Miami is going to be how aggressively people seize their moment.

Tim Alberta: The DNC chairman, Tom Perez, is being much more aggressive than RNC Chairman Reince Priebus was four years ago in trying to winnow this field in a hurry. Basically, post-Labor Day, because of the debate requirements, there might only be five, six, seven candidates left who qualify for the stage.

Terry Sullivan: Being so aggressive at limiting [the number of candidates] is only going to end up hurting the more establishment candidates. Joe Biden benefits from a 20-person field. An eight-person field hurts Joe Biden, and in the same way that the law of unintended consequences brought about Donald Trump on the Republican side.

Beth Hansen: When you have arbitrary criteria that you’re [using], it might seem like a good idea now, but then after June and after July you’re stuck with the five or six candidates that you have, and you might want to rethink that. But by then, it’s too late. Part of running any campaign is this: It’s an arduous ordeal. It’s town halls and it’s donor meetings, and it tests those people who are going to be good at this. And I’m just not sure if cutting the field by that much that early on is actually going to be the best thing for them.

Jeff Roe: It’s remarkable. I haven’t heard a lot of people talk about how intrusive the consequences of these [DNC] decisions on what their measurements are needed to get into the debates. When you’re telling somebody how much prospecting email they have to [send], when your entire campaign is based on money management, that’s a really intrusive trigger. It also ratchets up what I think they’re trying to avoid, which is their lurch left. You’ve got candidates who otherwise would be talking about, ‘Well, I’m a capitalist, but I understand that we need to protect the underprivileged,’ and now, they’ll just have to go full-blown [left], or they will be punished immediately on email and Facebook and the other ways that they traditionally raise money. And so, if they’re trying to incentivize a mainstream nominee, which it seems to me that they’re trying to do, I think they’re going about it the wrong way.

Tim Alberta: To Beth’s point about this being a marathon and not a sprint, you think back on the Republican side, the winner of the Iowa caucuses in ’08 and ’12—Mike Huckabee and Rick Santorum, respectively—these guys were in single digits almost all the way until the final six to eight weeks, when they started to take off. You’re not going to be able to see anybody fly way below the radar like that for the next eight months and then pop in December, because they’re not going to be able to stay on the debate stage.

Jeff Roe: I think what [the DNC] has done with the proportional delegates is interesting. And with the removal on the first ballot of superdelegates, they’ve incentivized effectively a 45-day campaign. But you can’t—with these requirements, a candidate can’t lay and build a framework to exercise a campaign to then have momentum at the right time. They’ll be washed out because of the process, because of what the requirements are from funding. If you have 120,000 donors and you’ve been cranking on it for six months and you’re 10,000 unique donors away from making the next debate stage, as we know, that takes 80 or 90 grand that you might not have. So now, you’re sacrificing [hiring] staff for online fundraising.

Terry Sullivan: It’s not just that they’re making these campaigns contort themselves financially; it’s that they’re making them contort themselves on issues. It means the more of a bomb thrower you can be, the more likely you are to get hits online and the more dollars you’re going to raise.

Tim Alberta: You need those viral moments.

Terry Sullivan: You need those viral moments, so you’re going to become more and more extreme in what you’re saying in order to try to capture that.

Beth Hansen: It’s almost counterintuitive: You’re chasing the very things that are going to make it difficult for you to be a good general election candidate, because you’re incentivized to chase those things to be able to continue to participate in the primary.

Jeff Roe: So, the biggest differences are, because of the criteria being so stringent, it’s going to diminish substantially the number of people they can get on the stage. That’s No. 1. And I think No. 2 is the law of unintended consequences, i.e. superdelegates. The role that they play in the convention now, if the threshold, whatever it is—just under 1,900—is not met, then they basically come in and can anoint the nominee of the party.

Tim Alberta: Yes. For all the talk of superdelegates being sidelined on the first ballot, they could play a more decisive role than ever. They can swing the entire second ballot.

Jeff Roe: Yeah. On live TV.

On the Democratic Primary Voters

Tim Alberta: Let’s talk about the role ideology plays in all this. Trump proved that many Republican voters weren’t looking to the Club for Growth or the Wall Street Journal editorial board as their guiding light, ideologically speaking. They were looking for something that was a little bit more authentic and a little bit more populist. So, my question is: Do you all believe that the Democratic Party’s base is significantly farther to the left than they were four or eight or 10 years ago on a lot of these big issues? Or do you think that that’s all of us spending too much time on Twitter and CNN?

Danny Diaz: Well, you’ve got to weigh what you need to say and what you think gets you there versus should you get the job in governing, right? And people may disagree with that, but there’s a reality to that and they’re operating in a post-AOC world. So, there’s a lot of energy on their side with respect to that. It’s going to force the dialogue in a direction where there’s one ultimate beneficiary and his initials are D.J.T., 100 percent.

Terry Sullivan: I think the bigger thing is … people don’t care about issues. They’re going to claim they care about issues. But we haven’t trusted our government in a long time. We don’t trust our financial institutions because God knows what they’re doing. We don’t trust our churches anymore because God knows what they’re doing. We’re in a situation now where people don’t trust anything or anyone, and what they want is some sense of authenticity. It doesn’t matter what you believe; it matters that you believe it. And they saw that with Trump because, in their mind, no one would say crap that crazy because it was poll-tested. He seemed authentic. It was his perceived authenticity that mattered. So, when he said something that was completely against Republican orthodoxy, he doubled down on it. He tripled down on it. And they’re like, “Well, I don’t agree with it, but at least he’s not a politician.”

Tim Alberta: So you don’t believe the Democratic base is moving farther to the left?

Terry Sullivan: I believe they are; I just think it doesn’t matter on the issues.

Beth Hansen: That’s exactly what I was going to say.

Terry Sullivan: It’s personality-driven. Donald Trump did not get elected by his position on any issue at all, period.

Jeff Roe: Well, that’s the general. But during the primary, they care.

Terry Sullivan: Wait, wait. This is important. Ted was right on 10 times as many issues in the Republican primary electorate as Donald Trump.

Jeff Roe: And we called him a liar for everything that he said—and he’s actually followed through. Everything he said on the debate stage [were] the right things. We just called him a liar because he had a record that didn’t back it up. Now, he’s actually done it which is why he’s got a 90 percent approval rating.

Terry Sullivan: Yeah, but he’s all over the map on stuff.

Jeff Roe: Not during the campaign. Over his 72 years of life, he has been, but in the campaign, he actually said all the right things. He said he would appoint judges that were pro-life; he had a record of not being that. He said that he was with the NRA on all gun rights, and he didn’t have a record of that.

Terry Sullivan: I guess we didn’t talk about trade during the campaign.

Tim Alberta: If the issues don’t matter in a primary, then why the rush to embrace Medicare for All, which was a fringe position in the Democratic Party 10 years ago? Why the rush to embrace the Green New Deal?

Terry Sullivan: Because they’re missing the point. Because these candidates are missing the point, which is authenticity. People want a candidate that they can identify with, that they can believe in, that they believe is telling them the truth way more than one that agrees with them, whether they say it or not.

Jeff Roe: If Bernie Sanders was a moderate Democrat, he’d be at zero. If Mayor Pete, by the way, was straight, he would be at zero. So, it does matter.

Terry Sullivan: Mayor Pete being straight has nothing to do with where he’s at on the issues, and it has everything to do with whether they believe him.

Danny Diaz: Well, it’s identity—

Terry Sullivan: It’s identity. It’s identity. And that’s what I’m saying: Mayor Pete seems authentic. Mayor Pete is where he’s at because no one knows where the hell he’s at on the issues.

Danny Diaz: It’s identity politics on their side. There’s a greater premium placed on it than our side, I think. And I do think the party has moved to the left.

Beth Hansen: Yeah, that’s what I was agreeing with. I was actually not agreeing that issues don’t matter; I was agreeing that the Democrat Party has moved to the left. I actually think issues do matter, and that’s why they’re coming out with baby bonds and Medicare for All. They do matter, but the importance is the authenticity. The importance is whether or not what you’re saying is something that you believe in, and that’s where I think that Biden can actually—it’s not exactly a Rose Garden strategy, but if he can stay above the day-to-day fray and remind people that he has been a Democrat leader and somebody who is on their side and he can have that authenticity, he is going to end up being their nominee.

Jeff Roe: And both can be right, by the way. You can be a liberal and authentic, and that’s probably who will be the nominee.

Tim Alberta: We’ve talked a lot about Biden. We have not talked a lot about Bernie Sanders, the only other candidate in the Democratic primary who’s had that built-in floor of 18, 20, 22 percent nationally and in Iowa and New Hampshire polls. And look, these are two different races—the 2016 Republicans and 2020 Democrats—but I do think there are some parallels. And one big one for me is that I hear from a lot of Democrats, “Look, even if this guy wins Iowa, even if he wins New Hampshire, the party is not going to let him be nominated.” They say they will pull out the stops, they will do something to keep him from being nominated. And damn, does that not sound familiar?

Jeff Roe: It sounds awesome. [Laughter]

Tim Alberta: No, but really, we heard this same thing with Donald Trump four years ago. So, is there any reason to believe that if Bernie Sanders gets that head of steam—let’s say he wins Iowa or New Hampshire or maybe both—can you see a scenario in which the Democrats succeed where the Republicans failed four years earlier, which is to have a bunch of candidates drop out and coalesce around an alternative because they don’t want Bernie to be their standard bearer?

Terry Sullivan: Well, first of all, you’re never going to have a scenario where all the other candidates drop out, because you’re always going to have the John Kasich jackasses who are so fixated on their own ego that they can’t drop out to defeat the greater evil.

Jeff Roe: There we go! There we go!

[Beth Hansen rolls her eyes]

Terry Sullivan: At the end of the day, look, Bernie Sanders is a niche candidate. The only reason he became a top-tier candidate is he was running against the worst candidate in the history of mankind. So, he ran against Hillary Clinton and still lost. You had a freshman senator with two years of experience who beat her the first time he ran for office. You had Donald Trump on the heels of all sorts of offensive stuff he said, and the lowest points of his campaign beat her. So, the fact that Bernie Sanders got close is not some sort of badge of honor.

Danny Diaz: Well, I don’t think that guy is walking around with rose-colored glasses on. He knows he needs to meet the threshold on the first ballot on the convention floor or the thing will be taken away—

Tim Alberta: Or those superdelegates will take it away from him.

Danny Diaz: And who has—an open question—who has the operation in place at this juncture to do it?

Jeff Roe: Biden, maybe.

Tim Alberta: Beth, what do you make of Bernie Sanders?

Beth Hansen: I think his time was four years ago, and I think that he has, to Jeff’s point about a floor-ceiling of 25, 35, I just don’t think that four years—he made a big splash then against Hillary Clinton, and he was so different from Hillary. Hillary was establishment. Hillary was mainstream, and he was—he was out there. Now, there is just competition for that out there, crazy space, and I just respectfully don’t think that he is going to take it as far four years later. There are too many other people.

Jeff Roe: Sanders isn’t a niche candidate because he drives the agenda and he is authentic.

Terry Sullivan: I agree with that.

Jeff Roe: He ran a terrible campaign and actually was not in the campaign to win, as he self-expressed. He was in the campaign to advance his agenda. Now, he’s in the campaign to win. I just wouldn’t count the guy out because I think a lot of these other guys could really be flashes in the pan.

Danny Diaz: Look, man, you get through these early four [states]. Durability, organization, playing in a bunch of states—this thing is not going to be decided before March 3, OK? And if you can put in place the team that can allow you to gain a bunch of delegates on March 3, which he does, to me, it’s very hard to just like to cross him off the list.

Jeff Roe: And it’s who can get hot. I think this is a big thing about—it’s like the NCAA Tournament: Who actually has the ability to get hot and stay hot for 45 days? And he definitely has that. We’ve seen him do it.

Terry Sullivan: But it’s tougher to get hot a second time.

Beth Hansen: Yeah, that’s what I agree with.
  

On Defeating Donald Trump

Tim Alberta: I’m sure that you’ve all wondered what could have been done differently to defeat Donald Trump. And I’m wondering, is there a weakness of his that was not exploited four years ago that has become more apparent since? One that you believe the right Democrat with the right message and the right tactical approach could exploit in this general election campaign?

Jeff Roe: I’ll take a shot at this. You look at the state polling. National polling is great, but look at the state polling, which is kind of the better barometer here—the Rust Belt. It’s kind of like Johnny Obvious, but Pennsylvania, Michigan and, I think, kind of that blue-collar voter, to Terry’s point, that didn’t show up for Hillary. You can malign these people all you want. But they’re Obama-Trump voters, and that’s what’s in play there. And the question is—look, there’s a valid argument that a Bernie Sanders inspires them to some degree. There’s a valid argument that a Joe Biden, because of what he represents, can appeal to those folks. There are a lot of people in the Democratic Party right now that are asking, like, “Where do I fit? How do I fit into this scheme at the moment?” And I think the Trump team understands that; they are laser-focused on that. To me, that’s the play.

Terry Sullivan: I completely agree. And it’s actually two interesting groups. It’s the blue-collar Rust Belt folks, but it’s also the suburbanite Rust Belt folks who think, “You know what, I couldn’t ever vote for Hillary Clinton. I don’t want to vote for Donald Trump. I did just because it’s anti-Hillary, but you know what? If it’s maybe a Mayor Pete or a Joe Biden or someone that you can just hold your nose as a suburban probably soft Republican and vote for.” Those are the two things that he’s really got to worry about.

Tim Alberta: Because they all just did last November.

Jeff Roe: You had presidential-level turnout across the board, and Michigan elected a Democrat governor and Wisconsin elected a Democrat governor.

Terry Sullivan: And I expect you’re going to have record turnout this time. I think it’s going to be higher than [2016]—it’s trended up.

Beth Hansen: Your question was whether or not there was a weakness that had not been exposed in Trump. And I would answer that question that there is not, because I don’t think we have learned anything new about him—he is exactly the person that he said he was going to be. There’s nothing new. The question is whether or not in 2020 the voters want that.

Terry Sullivan: With those Rust Belt voters, it’s not going to be how it’s played out on TV. It’s their pocketbook. And that’s why it’s interesting on this trade stuff. We can talk about all of these other candidates, but the greatest impact on Trump’s reelection has nothing to do with who the Democrat nominee is and everything to do what the economy is. Because they’re willing to put up with his crazy Twitter shit and all the stupidity as long as the economy is good. The second their job is on the line or the prices are higher for them, it all goes out the window.

Tim Alberta: So, Jeff, I want your answer on the kryptonite to Trump, but before I do, just quickly on the Rust Belt because these are my people, and I feel the need to speak up for them. It’s interesting because all of mythologizing of Trump in the Rust Belt and connecting with these forgotten voters, Donald Trump wins the presidency off of three states, Michigan, Wisconsin, Pennsylvania—

Jeff Roe: 100,000 votes combined—

Tim Alberta: 77,000. It was 77,744 votes combined in those three states. And Hillary underperforms Obama 2012 in those states by 600,000 votes. So, it’s not just the question of the Obama-Trump voters; it’s the question of the Obama voters who stayed home, right? And the folks who felt so disillusioned by the general election campaign in 2016 that they just didn’t come out and cast a ballot and a lot of Democratic voters or lean-Democratic voters who just could not bring themselves to go out and vote for Hillary Clinton as much as they may have disliked Donald Trump. I wonder if Democrats are at risk of not nominating someone who can bring those people out.

Jeff Roe: They’re positioned to have an identity politics nominee. They also are going got take the bait. Terry, I respectfully disagree this time. If I have one more of these [points to cocktail] I’ll disrespectfully disagree.

Tim Alberta: Get this man another drink.

Jeff Roe: Tariffs are like a red herring. That’s a negotiating tool. If you want to take a position of who is going to hold China and Mexico hostage over tariffs to get a better deal—whether it’s a better deal, whether the deal was already done, it doesn’t matter. That’s for New York Times A18 readers. That is winning politics in those states.

Danny Diaz: It’s got to be weighed against the Sunbelt right now. And I’m thinking like Georgia, particularly if [Stacey] Abrams gets in the Senate race. I’m thinking Arizona.

Tim Alberta: Let’s throw Texas in there.

Jeff Roe: If I was going to run a [Democratic] campaign and I was thinking tactically, I would be up early, very early, attack early, because you can get him from talking about the issues he cares about. Give him Florida. You can fight like a dog the whole time, but you’re not going to win. Do not fight for Florida. I know you’re supposed to, but just let it go.

Tim Alberta: You could even give him North Carolina.

Jeff Roe: You could even give him North Carolina. I probably wouldn’t.

Terry Sullivan: Florida is crazy like Trump; North Carolina is different.

Tim Alberta: But you come back and win the Rust Belt, and you don’t need Florida or North Carolina. It doesn’t matter.

Terry Sullivan: If you’re going to expand the map, go do it out West. Not Texas, but real out West. I think there’s some ways to do it.

Jeff Roe: Do things that [any other] Republican would get assaulted for doing. He could do a deal for Dreamers and a wall, and every Republican would take it.

Tim Alberta: Right, which a President Jeb Bush or Marco Rubio would never be able to get away with.

Jeff Roe: And because of his latitude that he has with Republicans, he could actually do this tariff fight and I don’t think voters care. They do not care about trade. They care that he’s fighting for them.

Terry Sullivan: Absolutely.

Jeff Roe: And he’s fighting the Mexicans, and he’s fighting the Chinese.

Tim Alberta: Beth, as a fellow Midwesterner, why don’t you have the last word here. Can Donald Trump be defeated in those Rust Belt states by the right Democratic candidate, even if, as Jeff was saying, many of those voters feel as though he’s fighting for them?

Beth Hansen: The economy is going to be important, to Terry’s point. The economy is going to be important, but what’s also important is the number of people who were voting for Donald Trump because they were voting against Hillary Clinton. And I think that that was particularly pervasive—I’m a Michigan native, I live now in Ohio, and I think that was particularly pervasive there. So, I really think it’s up to Democrats to nominate somebody who can actually be competitive in those states.

Jeff Roe: And who besides Biden?

Beth Hansen: Well, I think it’s Biden.

Jeff Roe: That’s it.

Beth Hansen: I wouldn’t say that’s it, but he’s the obvious one.

Terry Sullivan: If he’s the nominee, he would be the front-runner.

Jeff Roe: Who could they nominate that would be a coin-toss favorite the day after the Democratic convention—besides Biden?

Danny Diaz: I think Harris is a sleeper in that category.

Terry Sullivan: I think Mayor Pete only because he seems authentic. Who knows—

Beth Hansen: I just don’t think he’s—

Terry Sullivan: He has the ability to blow up, but he seems authentic.

Danny Diaz: Let’s remember, a great July does not equal a great October.
  

On November 2020

Tim Alberta: Complete this sentence: Donald Trump wins reelection if…

Danny Diaz: If the Democrats nominate somebody who is ideologically not on par with the general election electorate, by and large defined by voters who don’t have a place at the Democratic table.

Terry Sullivan: That was a long answer.

Danny Diaz: It was the correct answer.

Terry Sullivan: Elizabeth Warren.

Tim Alberta: Wait, he wins reelection if she’s nominated?

Terry Sullivan: Right. Your question was, he wins if the Democrats nominate … and I said Elizabeth Warren.

Danny Diaz: There are like 20 names that you could fill in—

Terry Sullivan: There are, but she is the most awkward individual. It has nothing to do with her being a woman. It has nothing to do with her being a Native American and all of her tribal ancestry. It has everything to do with like she’s weird, she’s awkward. And so, he’ll beat her like a drum.

Tim Alberta: Jeff, Donald Trump wins reelection if…

Jeff Roe: Dow Jones stays about 24,000. Job growth continues. And they nominate somebody to the left of the Democrat Party.

Tim Alberta: Beth, Donald Trump wins reelection if…

Beth Hansen: Summarize everything that this auspicious group has said. If they nominate somebody who is out of step, inauthentic and doesn’t have the ability to appeal to regular people the way Donald Trump does. And if they nominate somebody who is out of step with that and the economy stays good, he is going to be reelected.

Danny Diaz: One point on the economy: I don’t think the economy needs to be great through November of the election year.

Beth Hansen: Agreed. It doesn’t have to be great.

Danny Diaz: I think it’s baked in during the summer, and at that point, it’s a done deal.

Tim Alberta: Terry, we’ll start with you: Democrats win back the White House in 2020 if…

Terry Sullivan: They can get out of their own way.

Tim Alberta: Elaborate on that. If they can get out of their own way, in what sense?

Terry Sullivan: Look, Donald Trump can win when he makes it about his opponents and their weakness. You asked how you beat Donald Trump. The way to beat Donald Trump is to make Donald Trump the issue, not you. He’s got this approach to dragging you down in the mud pit with him. Make him the issue and not you, and you can rise above it. I think the trick is, Trump is his own worst enemy; don’t get in the way of that.

Tim Alberta: Danny, Donald Trump is defeated if…

Danny Diaz: I’m going to take a different tack here: If [Democrats nominate] somebody who can get in the ring with what is a great prizefighter and who can kind of manage him and deal with him and deal with the counterpunch, because he is a great political athlete and he will find that weakness, he will exploit that weakness, and he will take advantage of it to the greatest degree possible.

Tim Alberta: Beth, you’re nodding.

Beth Hansen: Yeah, I think that the Democrats are going to win when they find somebody who can get in the ring. But importantly, they’re not going to be distracted and they’re not going to take the bait. They are going to win if they are able to get into the ring and fight. But at the same time, convince people that they care about them, that they are authentic. It’s going to have to be something different. It cannot be that I’m going to be unlike the policies and programs of Donald Trump. It’s going to have to be something different, and if they can articulate something different and make it authentic and something that resonates with people and stays in the ring without getting distracted, they will win.

Tim Alberta: Jeff, Democrats win back the White House if…

Jeff Roe: I think history holds on this. I know we’re in new times and that we’re trying to think about things in ways because everything has changed in the last 10 years, but I think the normalcy of politics holds. You don’t lose reelection unless the economy is a mess. So, I think they need two things. They need the economy to take a downturn and they need a message of what their candidacy would change. [Trump] has taken very populist, outside-the-norm positions that the Republicans accept because he’s doing so much for them and because he’s a standard bearer and he fights the Democrats every day. They would have to have an economic downturn and they would have to have an overwhelming message that 51 percent could get behind—51 percent of the Electoral College. They’ll probably win the popular vote. But I don’t see anybody that does that if this continues the way it is. You still lose. That math holds up. That’s why we all thought we were running. It didn’t matter [that] Hillary was the worst [candidate] in the history of the world. It was only 100,000 votes. I get all that. But a Republican was going to win last time. I think any of our people—it pains me to say, even Kasich probably would have won.

Terry Sullivan: But Jeff, I think that so much is out the window now—

Jeff Roe: To defeat an incumbent something has to be wrong and nothing is wrong.

Danny Diaz: It’s very dangerous to judge this by viewing it through the prism of a referendum. It’s a big, big mistake. It’s [got to be] a choice, and I get back to my kind of two people in the ring with a prizefighter.

Tim Alberta: Jeff, when you say nothing is wrong, nothing is wrong on paper. But in November 2018, you have all these suburban congressional seats that had been held by Republicans for 10, 20, 30, 40 years from the Salt Lake suburbs to the suburbs of Detroit, where suddenly they’re flipping. And that’s while the economy is booming. So clearly, some individuals, including a lot of traditional Republican voters, did believe something was wrong.

Jeff Roe: Ronald Reagan had some tough midterms, and he did pretty well.

Terry Sullivan: I know Donald Trump. I’ve seen him on TV, and Donald Trump is no Ronald Reagan.

Jeff Roe: I never said he was.

Tim Alberta: So, you’re all tasked in a hypothetical universe with getting Donald Trump reelected. You are Brad Parscale [Trump’s 2020 campaign manager]. It’s your job to get him another four years in the White House. Who is the one Democratic candidate you do not want to see next November?

Beth Hansen: I think Mayor Pete. If Mayor Pete takes off—and I’m not sure that he has got enough experience as a mayor—but if he takes off, I think that is a very difficult race for him.

Danny Diaz: I want to say Joe Biden because it’s like the easy answer to give, but I also want to say Bernie Sanders. And I want to say despite being kind of quote “wrong” on a lot of issues, he brings into play a dynamic that I think is kind of interesting from a general election perspective, to be very honest with you.

Terry Sullivan: I don’t disagree with Danny, other than I wouldn’t work for Donald Trump out of conscience.

Danny Diaz: Can I add one thing? Once again, the sleeper—Kamala Harris.

Terry Sullivan: Yeah, I think she’s real. She’s real because she can go the distance.

Jeff Roe: I think the only one that’s a worry is Biden. I think the rest—I don’t think it’s any layup at all, but I also think that the president will get the highest number of African American votes that we’ve seen for a long time.

Tim Alberta: Terry, Marco Rubio had an otherwise really good debate performance in Manchester except for that—

Terry Sullivan: Other than that, Mrs. Lincoln, how was the play?

Tim Alberta: Yes, exactly. We all know that moments are sort of the currency of a presidential campaign. Those moments, those inflection points that people remember that inform perceptions of candidates and campaigns and that shift the narratives at a fundamental level. I’m wondering, have any of you seen a moment in this early stage of the 2020 Democratic race, a moment that you feel has that capacity for sort of reshaping the narrative, reshaping the perception of candidates and of the field at large?

Danny Diaz: Not yet. It’s early.

Terry Sullivan: I think there’s one. I think it’s Joe Biden’s response to all of these women rolling out with the #MeToo [allegations], and he’s not apologizing. I think that that proves that their campaign has their crap together, that they’ve thought through stuff and that they’re built for the long haul. Because he was damned if you do, damned if you don’t. If he would have taken the bait and said, “I’m sorry,” no one would have believed it —he would have seemed fake and phony. He’s a creepy old man. That’s who he is, and he kind of doubled down on it. He genuflected in the direction of [it], and he acknowledged that it’s kind of creepy. But he didn’t apologize, and I think that was a telling moment that he didn’t do that. And I think it matters.

Jeff Roe: I think it’s early.

Beth Hansen: I think it’s early.

Jeff Roe: I think Biden reading his notes on Hyde, we will see in an ad.

Danny Diaz: I agree with you on that.

Jeff Roe: And the press tick-tock, which is stunning at this moment in a campaign—I completely disagree with them having their shit together. It could not be further from the truth in my opinion, because of what we read in the follow-up of how he arrived at his decision. The blow-by-blow of liberals on his campaign that were going to walk from the campaign if he didn’t change his position. That is a weak-sauce operation. He’s on the teleprompter, which—I was interested in that moment. I follow politics fairly closely, and all of a sudden, he just looks down and starts reading what he now believes about abortion. And watching that was a moment for the entire party. To watch a person flip on abortion and federal funding of it, and have to read his notes—it felt like exactly what they said it was, which was a campaign manager going to him and saying, “You’ve got to flip.” And his campaign people threatening to revolt. I think that is the first nail in what will eventually be a November coffin for him.