Why Ron DeSantis' campaign is struggling

Download Audio
Florida Governor and Republican Presidential candidate Ron DeSantis marches in a Fourth of July parade, July 4, 2023, in Wolfeboro, New Hampshire.(Andrew Lichtenstein/Corbis via Getty Images)
Florida Governor and Republican Presidential candidate Ron DeSantis marches in a Fourth of July parade, July 4, 2023, in Wolfeboro, New Hampshire.(Andrew Lichtenstein/Corbis via Getty Images)

Florida Governor Ron DeSantis launched his 2024 presidential run with several advantages, including his brand as "Trump, plus competence" and lots of money from big donors.

"Clearly major donors want to move on from Donald Trump, and there is a lot of money being spent to try to defeat Donald Trump," Alex Conant, Republican strategist and founding partner at Firehouse Strategies, says.

But running as "Trump-not-Trump" has put DeSantis in a tough spot — and it’s showing in his sagging poll numbers.

"He wants to be able to criticize Trump, but he does so very softly," says Tim Miller, writer-at-large for The Bulwark. "He pussyfoots around the issue and then he repeats Trump’s talking points."

Today, On Point: Why Ron DeSantis’ presidential strategy isn't working.


Tim Miller, Writer-at-large for The Bulwark. Co-host of The Next Level podcast. Former communications director for Jeb Bush’s 2016 presidential campaign. Former spokesman for the Republican National Committee during Mitt Romney’s 2012 Presidential campaign. Author of "Why We Did It: A Travelogue from the Republican Road to Hell."

Mary Ellen Klas, State Capitol bureau chief for the Miami Herald.

Alex Conant, Republican strategist and founding partner at Firehouse Strategies. Former communications director for Marco Rubio’s 2016 presidential campaign and Tim Pawlenty’s 2012 presidential campaign.


Part I

ANTHONY BROOKS: So what's happened to Ron DeSantis' presidential campaign? When the Florida governor launched his bid for the White House this past spring, he seemed to have a lot going for him. He's a conservative governor with discipline and a winning record.

GOV. RON DESANTIS: So we just completed the boldest and most far-reaching agenda that we've seen in the modern history of the Republican Party.

BROOKS: In a not-so-veiled swipe at the Republican frontrunner, Donald Trump, DeSantis says it's time for the GOP to end the culture of defeat. DeSantis is running as the nations leading cultural warrior. He signed one of the toughest abortion bans in the country, cracked down on LGBTQ rights, picked a costly fight with Disney while promising to oppose wokeness.

DESANTIS: We reject woke ideology. (CROWD CHEERS) We fight the woke in the legislature. We fight the woke in the schools. We fight the woke in the corporations. We will never ever surrender to the woke mob. Florida is where woke goes to die! (CROWD CHEERS)

BROOKS: But his campaign has struggled to take off. He's running second among GOP presidential hopefuls, but his poll numbers are stagnant. So far, he's unable to close that large gap against Trump. His big donors are hitting pause. He's laid off campaign staff and his campaign is trying to reset.

I'm Anthony Brooks in for Meghna Chakrabarti and this is On Point. This hour, Ron DeSantis' campaign hits some stiff headwinds. Can he right the ship?

Joining me now from New Orleans is Tim Miller, writer at large for The Bulwark. He was communications director for Jeb Bush's 2016 presidential campaign and spokesman for the RNC during Mitt Romney's 2012 presidential campaign. And Tim, welcome back to On Point. It's good to have you.

TIM MILLER: Hey, Anthony. Good to be with you.

BROOKS: So what ails the DeSantis campaign? There's a lot to talk about, but sort of start us off with a quick summary of your view about what's going on.

MILLER: Yeah. Well, I'm glad we have a full hour to discuss it because there is plenty to discuss. (LAUGHS) 


MILLER: I would sum it up this way. Ron DeSantis had a really good elevator pitch last November and December to Republican primary voters and that was essentially: "I can give you all of the MAGA stuff that you like. And I can do it while actually winning. And I proved that I could do this in Florida. Florida used to be a swing state. I won an overwhelming landslide in the midterms. All the handpicked candidates Trump picked, they all lost in Pennsylvania and Arizona. Stick with me. I can give you almost all the Trumpism and we can actually do it. We can actually get stuff done."

And I think that was a good message at the top level, and that's why he was close to Trump in the early polling around Christmas. The problem is the devil then got into the details. And once he started campaigning, he lost on two fronts. One, the more college-educated, center-right type of Republicans who were attracted to him were really turned off by these culture war fights, trying to get to Trump's right on gay rights and such. And then, the MAGA voters were not really impressed with his electability pitch. You know, once they saw him up close under the bright lights, he didn't seem like that strong of a campaigner.

So he's lost altitude with what should have been his core base in this primary. And he's gotten away from that elevator pitch that was serving him well last winter.

BROOKS: Yeah, really interesting. So let's talk a little bit about his agenda and how he sounds on the campaign trail.

So, in May, Gov. DeSantis signed into law bills targeting the LGBTQ community, including expanding the state's law prohibiting instruction about sexual orientation or gender identity in schools, and also a ban on drag shows in front of children. Here's what he had to say at the signing:

DESANTIS: I feel very strongly as governor, but also just as a dad of a six, a five and a three-year-old that, you know, we need to let our kids just be kids. And we have a very crazy age that we live in. There's a lot of nonsense that gets floated around. And what we've said in Florida is we are gonna remain a refuge of sanity and a citadel of normalcy. We're not doing the pronoun Olympics in Florida. It's not happening here. (CROWD CHEERS)

BROOKS: And here's one more cut. Here's Ron DeSantis stumping in New Hampshire in May. He's talking about — he's talking against — the idea of diversity, equity, and inclusion programs.

DESANTIS: So our view is that DEI, really the way its practiced stands for discrimination, exclusion, and indoctrination. And that has no part — (CROWD CLAPS)

BROOKS: So Tim, talk a little bit about that agenda. How does this poll with moderate voters, for example, this culture warrior stuff?

MILLER: Well first on the merits, I think it offends a lot of the suburban voters that have left the Republican party and that might have been attracted to somebody else besides Donald Trump.

I mean, look, just speaking personally as a gay dad you know, my kid gets to be a kid too, right? And teachers can, shouldn't be banned from explaining, you know, that gay families exist, the trans families exist and I think that's something that turns off the types of people that were looking for someone else besides Trump who are Republican voters.

So, so I think that starts — and what you see here is this symbiotic relationship. The more DeSantis tries to get to Trump's right on these culture issues — you listed out so many, but you didn't even mention, you know — on immigration, he's tried to get to Trump's right, on Covid vaccines, he's tried to get to Trump's right. So the more you go to the far culture war right to try to appeal to MAGA voters, the more the remaining kind of center-right voters in the party look at the DeSantis and go, "This guy isn't any better than Trump."

One of the things that maybe some of your listeners might not appreciate is that Trump does well not just with very conservative voters at the Republican primary, but with moderate voters. A lot of moderate Republicans — it seems crazy to me, it might seem crazy to listeners — look at Trump and they say, "Eh, he doesn't really believe this stuff on the religious issues. You know, he doesn't go as hard right on Social Security. He's not as, you know, hard right on national security issues." And so they see Trump as kind of a heterodox Republican. And so DeSantis now finds himself losing ground with that group to Donald Trump.

BROOKS: Yeah. Really interesting. I mean this — I wanna ask you a little bit about this Trump challenge and actually it's a challenge that I think applies to all of the GOP candidates.

So here's DeSantis. He sat down recently for a rare interview with mainstream media last week when he spoke with CNN's Jake Tapper. Tapper asked him about special counsel Jack Smith's investigation into Trump's alleged effort to upend the 2020 election. Listen to this:

JAKE TAPPER: If Jack Smith has evidence of criminality, should Donald Trump be held accountable?

DESANTIS: So here's the problem. This country is going down the road of criminalizing political differences, and I think that's wrong. Alvin Bragg stretched a statute in Manhattan to be able to try to target Donald Trump. Most people, even people on the left, acknowledge if that wasn't Trump, that case would not have likely been brought against a normal civilian. And so you have a situation where the Department of Justice, FBI have been weaponized against people they don't like.

BROOKS: So there is DeSantis talking about a Department of Justice being weaponized against people they don't like, rather than misbehavior by his rival Donald Trump. I mean, I'm puzzled by this.

MILLER: He's repeating Donald Trump's talking points about these investigations. And here is just, I think, the fundamental flaw of the DeSantis campaign, right? He looks at Donald Trump and instead of his pitch to Republican primary voters being, "This guy is gonna be under indictment. This guy's a proven loser. Stick with me. I'll give you the policies you like and actually win." You know, he is echoing Donald Trump's talking points on the indictments and he's trying to get to Trump's right on the cultural issues.

I — if you look at Donald Trump and you say, "My criticism of you is that you're too nice to LGBT people and my criticism of you is not that, you know, you have run a criminal enterprise." There's a very small audience for that message. And so for some reason, he's chosen to attack Trump on these policies, getting at him from the right, rather than going at him over his criminal behavior and over the electability issue, which might have, you know, a better chance of resonating with some of these Republican primary voters.

BROOKS: But I guess — you say for some reason, and I guess that reason is that he's being cautious about alienating, right, the sort of Trump base?


BROOKS: So is the thinking here, do you think --


BROOKS: I mean, "Don't alienate those Trump folks because maybe Trump falls down and is out of the race by the time, you know, the Republicans pick a nominee." Is that the thinking here?

MILLER: I definitely think that's the thinking for your Tim Scotts of the world, you know, right, the lower candidates who are just kind of hoping that something happens. "Maybe the justice system will take care of Trump for us." If you're Ron DeSantis though, you should not just be wishing for an exogenous event to help you. I mean, you were close to tied with Donald Trump when you first started to consider getting into this race.

And so I understand not wanting to alienate MAGA voters. I don't think you should sound like a Never Trumper like me or The Bulwark and just attack Trump over every issue if you're trying to win this race — Chris Christie, for example, God love him — like that's not a path to victory. But still, you have to pick your spots.

And I would think that the fact that Donald Trump is set to be facing trial in the middle of the general election next May — not on the Alvin Bragg case, but on the documents case — should be something that you can make a case to Republican voters on and say, "Hey, you know, maybe, you know, the Department of Justice has gotten over its skis in certain ways but we can't nominate somebody that has been indicted three times and that has been a proven loser." That at least seems like a plausible path to victory. And he's not even trying that.

BROOKS: Yeah, I mean, he makes reference to this. "We have to overcome this we have to do away with his culture of defeat." But then he --

MILLER: Doesn't say who he is talking about.

BROOKS: Doesn't say who he is talking about. Here's another piece of tape. This is Neil Levesque. He's director of the New Hampshire Institute of Politics at Saint Anselm College outside of Manchester, New Hampshire. He was talking about the impact of Donald Trump on the DeSantis campaign. Here's what he said:

NEIL LEVESQUE: We've seen sort of a seesaw effect with DeSantis. As soon as Trump got indicted, DeSantis started to sink despite the fact they were spending large amounts of money in mail and on television here in New Hampshire. So in the background on everything that happens, Trump is standing right there.

BROOKS: Tim, do you agree with that? And if so, what's the best approach that DeSantis should or could take?

MILLER: Yeah, I'd say there's a little bit of a correlation-causation question there, right? Because around the same time of the indictments, two other things were happening. One, Donald Trump started to attack Ron DeSantis aggressively. He's attacking him as a phony. He's attacking him and saying he wants to steal people's social security and Medicare. He's going right at him personally in a very aggressive manner.

And here's another thing that was happening around that spring, Ron DeSantis was advancing all of these far right policies that we talked about in the Florida legislature: the six week abortion ban, et cetera. So DeSantis has started to drop while he's moved to the right while Trump has attacked him and while these indictments are coming down.

So there's been this confluence of events and to me, I think going right back at Trump in the same way Trump is going at him is the only way to plausibly, you know, get back his position. Besides, again, hoping that the justice system takes care of Trump for him but the timing just doesn't work out there. Iowa's coming up in January.

BROOKS: Right. And speaking of signs of trouble for the campaign, they laid off about a dozen staffers last week. The campaign has postponed paying some big bills. His poll numbers are stagnant as we mentioned. He raised a lot of money from mid-May to June, but more than two thirds of that came from big donors who have maxed out and can't donate again. So we're talking about some real challenges here.

We're talking about the fortunes of Ron DeSantis' presidential bid for the White House. When we come back, we'll go to Florida, check in on his track record as governor, and to see what his standing is with Republican voters in his own state. Stay with us. Tim Miller, stay with us. We're glad to have you.

Part II

BROOKS: We're talking about Florida Governor Ron DeSantis and his bid for the Republican nomination in the presidential race. His campaign is facing some strong headwinds. His biggest donors have hit pause. His poll numbers are stagnant. He's trying to reset his campaign.

I'm talking with Tim Miller. He is writer at large at The Bulwark and co-host of The Next Level podcast. And I'd like to bring in Mary Ellen Klas right now. She is state capitol bureau chief for the Miami Herald, and she joins us now from Tallahassee. Mary Ellen, it's great to have you. Thanks for joining us.

MARY ELLEN KLAS: Good to be here. Thank you.

BROOKS: So we wanted to talk to you because we sort of wanted to get a sense of how DeSantis governed in Florida as a way to sort of understand what he's doing now. But give me your reaction to what you heard from Tim Miller just about, you know, what you're observing and what you think is ailing this campaign right now?

KLAS: Well, I think Tim really hit the nail on the head on the fact that Ron DeSantis' approach — and certainly in Florida — has been to, you know, position himself to the right of Donald Trump. And there have not been any Florida specific, very many Florida-specific polls, so it's hard to get a sense of how Florida voters view him.

But I think there is --  there was one last week, a small poll by Florida Atlantic University that indicated, just as Ron said, that people are, you know, if a choice between Ron DeSantis and Donald Trump, Donald Trump is leading DeSantis by double digits.


KLAS: And part of the reason for you know, his success in Florida is really how he managed Covid. And how he, you know, emerged from that and kind of pushed the envelope. And then I think what he thought he could do is continue to, you know, he thought his instincts were were unique and and somehow everything he could do and touch was a winning formula. And I think we're learning that maybe that's not exactly the case.

BROOKS: Right. And so when you talk about how he managed Covid. He was pro-vaccine — if I'm getting this right, and correct me if I'm wrong — for elderly folks, but then he sort of backed off being super enthusiastic about vaccines for the whole population. He opened the state up early and really claimed that this was sort of a — and claims today — that this is really a kind of personal freedom issue.

And he talks about about opposing Fauci, referring to Anthony Fauci, the chief medical examiner to the president. So how did that play in Florida?

KLAS: Well, you know, he did do something that nobody — not very many Republicans or Democrats were doing, and that was countering the establishment message on both closing schools and businesses. And that was all happening before the vaccine.

And then once we had the vaccine, he initially started to promote them. But very quickly realized that, once Republicans and the base were kind of anti-vaccine, he embraced that messaging completely. And not even, you know, and actually had — called the legislature in for a special session to ban mask and vaccine mandates. And the result was that even though numbers in certain age groups were rising — numbers of cases and even death — the state was opening and the economy was more robust than many other places. As a tourist economy, we were rebounding faster than the rest of the nation.

And people I think were very pleased with that. And they rewarded him when he ran for reelection. They gave him a 19 point reelection victory.

BROOKS: So Tim, when I see DeSantis — and I've seen him a couple of times now when he's been through New Hampshire — he makes a big deal about this approach to Covid and really links it to this sort of personal liberty agenda, if you will. Good idea? I mean, is that part of the problem or is that part of the potentially winning message?

MILLER: No, it's part of a potentially winning message with Republican voters and it might not resonate with all listeners of the show. But Republican voters liked his approach to Covid and I think that was part of his winning formula when he was closer to Trump in the polls back in November and December. They thought he handled it well.

Here's the problem though: Covid, especially in Republican world, is basically over. It's a non-entity, right? So if you're gonna be trying to talk about it in January 23 before the New Hampshire primary you need to have a another message besides that and a separate contrast.

And I think that what DeSantis missed is, you know, he had this appeal in Florida --Mary Ellen can maybe speak to this — of he kind of governed as more of a traditional Republican, though his rhetoric was very MAGA, right, for the first two or three years and going through Covid. And I think that allowed him to kind of balance, you know, doing well with the suburban voters who had left Trump with also doing well with MAGA voters.

But then in this last year, as he prepared for this campaign, he got rid of that balance and just went hard right on everything from Covid to all these other cultural issues. So I think had he — had he gotten that balance back and had Covid being one piece of it, it could be part of the message, but he's gotten away from it.

BROOKS: Interesting. Mary Ellen, talk a little bit about that, about how he governed in Florida as a traditional Republican. Is that the case? And if so, describe how that worked.

KLAS: Well, it — he did start you know, pretty — actually going beyond where most conservative Republicans have in the past. For example, he acknowledged that climate change was a thing. He didn't use those words, but he talked about rising seas and he put a lot of money into resilience and protection against, you know, coastal flooding and acknowledging that the environment is something that was essential to Florida and its future.

That was something that really earned him, I think, a lot of support from people across the board. And he you know, embraced sort of the moderate messaging on a lot of things. He, early on, was a big advocate of school choice and advanced those issues which I think have a lot of kind of centrist support in the state. And those are the issues that he really elevated until Covid.

And then I think both the confluence of Donald Trump's reelection bid and the fact that Trump endorsed Ron DeSantis, and that's exact — that's what helped catapult him over the Republican favorite when Ron DeSantis was running for governor for the first time. And that allowed Ron DeSantis to have a relationship with Donald Trump that I think he felt he needed to help and exploit in many ways.


KLAS: In many ways. So what DeSantis did with Covid is as soon as Donald Trump started to realize that closing everything was not gonna be a good message for his reelection bid, Ron DeSantis started to tap into that and then started to push for the state to be open. And that was the — that resulted in an enormous amount of media attention and negative media attention. And that's when we first saw Ron DeSantis become very anti-media and sort of embrace that aggressiveness that Donald Trump had used throughout his tenure.

BROOKS: Right. Well, speaking of that I wanna actually play a clip at his first campaign event in New Hampshire early last month. DeSantis had this testy exchange with a reporter who tried to ask him why he's not taking questions from the press. So here's this back and forth:

REPORTER: Governor, how come you're not taking questions from voters?

DESANTIS: What are you talking about? I'm out here talking with people. Are you — are you blind?


DESANTIS: Are you blind?

REPORTER: I'm not blind at all.

DESANTIS: Okay. So people are coming up to me, talking to me, whatever they want to talk to me about.

BROOKS: So that was a little, may have been hard for listeners to get — to understand. The reporter was asking, you know, "How come you're not taking questions from voters?" Because DeSantis wasn't participating in sort of traditional town hall meetings that New Hampshire voters are very attuned to and used to. And DeSantis sort of snapped at the reporter, "Are you blind? I'm right here taking questions from folks after the event," but I wanna ask you both about that.

Tim, I'll come to you. There is this perception that he's an awkward campaigner, that he's not sort of warm and fuzzy. He doesn't sort of, hit that note. What do you think about that?

MILLER: Yeah, he's a bit of a prickly pear, as you could tell in that audio. And I think it works for him to a certain degree.

Look, Republican voters, whether you like it or not, don't like the media, right. And feel like the media's out to get them. And so when he was in Florida, and he could have those press conferences where he yelled at the media and like belittled these local reporters that — that hit a lot of Republican voters, you know, in their happy place, right? They liked that.

The problem is, you know, you can't then go and treat people that are showing up to your town halls like this, right? You can't treat people in diners like that. And so that, that kind of personality trait that worked for him in a press conference setting, you know, has not exactly worn well on the trail.

So I actually, I don't think that is his fundamental problem, but it's certainly not helping. And especially if he's making this pitch as the electability candidate. If voters look at him and they're like, "Man, you're not very likable. You're prickly." Donald Trump on the other hand, you know, he does a standup routine on stage. People start to get less sure that he actually is more electable.

BROOKS: Right. Mary Ellen, it's interesting to note — and a lot of listeners know this, of course — Ron DeSantis won reelection by 18%. It was a pretty convincing reelection win, and that is sort of part of his whole pitch about why he's a winner and why he can win again and get things done. But what explained that impressive reelection victory?

KLAS: Well, Florida is neither New Hampshire nor Iowa. And you can win reelection here by running television ads and, you know, just doing the big picture, not a lot of handshaking one-on-one.  And that is how that's — First of all, he ran on his record and the message of opening Florida during Covid. And that's what helped him enormously.

He managed to gain traction in places that had been going, that had been, you know, places like Miami-Dade County. The Hispanic vote, you know, worked — the Hispanic voters moved towards DeSantis in a really significant way across the state and specifically in Miami-Dade, which went from being a blue county to a red county.

And those are the — those kinds of inroads really managed to not only secure his lead, but give him the appearance of being, you know, the biggest winner we've seen on the Republican stage in a very long time. He also, you know, during Covid, a lot of people moved to Florida from other states and because they liked his messaging, many people that moved registered as Republican, so the Republican registration rolls for the first time exceeded those of the Democrats. And although independents in Florida continue to be the fastest growing segment of the electorate, many of those independents obviously voted for DeSantis or he would not have won.

BROOKS: I wanna ask you both about a couple of key people behind the DeSantis campaign, jsut to get a sense a clearer sense of who DeSantis is as a governor and as a candidate. So, Christopher Ruffo, lately of the Manhattan Institute, very much a force, as I understand it, in DeSantis' campaign against wokeness. Tim Miller, what do we know about Christopher Ruffo?

MILLER: Sure. He was a a right wing policy wonk, if you will, who really made his bones pushing, you know, these anti-woke policies, particularly in schools. You know, going up against not only the DEI, which is, you know, the hiring of diversity initiatives. But also on curriculum and how this curriculum was now, you know, the pendulum had swung too far the other way and was spending too much time talking about diversity matters and not enough time teaching traditional classics, things written by white men.

And so Rufo got put into — DeSantis put him into the New College to try to reformat this, you know, classically liberal arts college in Florida. And they're trying to reorient it into a more of a conservative college in the mold of Hillsdale. And so, so Rufo, I think that's somewhat interesting in how you think about how DeSantis thinks about education policy.

It's also interesting though in that Rufo is very popular in this kind of tiny little insular world of super online, culture-warring far right activists. And he was very popular and well-known there. And so for DeSantis to pick somebody from that world and say, "Oh, I want you to oversee a college, you know, despite the fact that is not your background at all." I think shows that he got very kind of wrapped up in this world of the types of people that post online you know on Twitter and on social media about right-wing cultural issues. And I think that his campaign's been very myopic in that way. And Rufo is a representation, a manifestation of that.

BROOKS: Yeah. I mean, if I'm recalling what I read about Rufo, I mean, one of the things that he sort of talks about — sees as sort of this campaign against wokeness as being important because the fears of grooming are somehow all wrapped up in — allowing teachers to teach about things like slavery somehow softens kids up for groomers. I mean this — he's pretty out there, right?

MILLER: Oh, he's very out there. Yeah. And I don't know if that's exact — if the race stuff. I think it's both, right? Like he is talking about how the racial issues, you know, are creating a more divisive, a more polarizing classroom where all kids care about now is race and they put racial identity first. I think that's his critique there.


MILLER: But then on the LGBT issues, that these teachers are grooming kids to be gay or bi or non-binary by teaching them at too young of an age about the existence of you know, about the fact that gay people and trans people exist in the world. And so I do think that, you know, helped formulate DeSantis',  so-called "Don't Say Gay" policy.

BROOKS: Right. And Mary Ellen, Casey DeSantis, his wife reportedly very involved in the campaign, correct?

KLAS: Yeah, I mean, that seems to be what we've watched throughout his tenure as governor. His closest advisor has been his wife. He keeps a pretty tight group of people — very loyal, very young, often, very inexperienced — and he relies on those folks and Casey for his primary bit of advice.

BROOKS: Listen we're gonna go to a break. Mary Ellen Klas, state Capitol Bureau Chief for the Miami Herald, joining us from Tallahassee. Mary Ellen, it was great having you. Thanks so much. We really appreciate it.

KLAS: Thanks for being here. I appreciate it, too.

BROOKS: And Tim Miller, writer at large for The Bulwark and co-host of The Next Level podcast. He was communications director for Jeb Bush's 2016 Presidential campaign. Tim Miller, stick with us. When we get back, we're gonna talk more about DeSantis' campaign and how he might turn things around with donors big and small, whether he can ultimately unseat Donald Trump as the party's nominee.

Part III

BROOKS: This hour, we're talking about Ron DeSantis' presidential bid and what looks like at least appears right now as a bit of a stall. I'm talking with Tim Miller, longtime Republican political operative, and now a writer at large for The Bulwark.

And I'd like to introduce Alex Conant. He's a Republican strategist and founding partner at Firehouse Strategies. He was communications director for Marco Rubio in 2016, his presidential campaign, and Tim Pawlenty's 2012 presidential campaign. But he is not currently working for any candidate right now. Alex joins us from Washington, D.C. Good to have you, Alex. Thanks for joining us.

ALEX CONANT: Hi, Anthony. Good to be with you.

BROOKS: So, I'd love to just start with a real quick sort of summary from you. I know you've been listening to the rest of the hour. What's your take on what ailes Ron DeSantis' campaign right now?

CONANT: I think it's two words: Donald Trump. I think Donald Trump continues to be super popular with Republican primary voters, and then he's had the good fortune politically — I think bad fortune legally, but good fortune politically — to dominate the headlines all over the summer. And as Tim and I know from 2016 when we were both working against Trump, when Trump dominates the headlines, it's very hard to gain ground on him.

And I think that has been the challenge for Ron DeSantis and everyone else running in the Republican primary, that for the last three months, Donald Trump has been on the front page of every newspaper more often than not. And as a result, it's very hard for any other candidate to, to gain ground on him, especially Ron DeSantis, who I think had some momentum earlier this year but has really struggled to keep it going with Trump ascendant.

BROOKS: Well, so if the challenge is Donald Trump, then it's probably worth sort of questioning his approach to Trump. And as Tim was pointing out, he's kind of going, trying to go around Trump a little bit instead of sort of just going through Trump. Would that be a viable approach?

CONANT: Yeah, and I think as we get closer to the debates and the primaries next year, Ron DeSantis is gonna have no choice but to sharpen his attacks on Donald Trump. At some point, he really needs to make the argument why he would be a better nominee than Donald Trump. And I think he's still — he has really tried to spend the first couple of months of his campaign introducing himself, laying out some policies to Republican primary voters, hasn't broken through. I don't think that means it's been an epic failure. It just means he hasn't broken through.

But I think as we get closer to these contests, it's important that he really sharpens his message to make it clear why he is a better choice than Donald Trump. And I think the time to really do that is this first debate in August, it's why I think Ron DeSantis really wants Donald Trump on that debate stage — why all the candidates really want Donald Trump to be on that debate stage because it'll make it much easier to make that strong contrast as to why they would be better nominees.

BROOKS: I wanna talk about money because we mentioned earlier in the hour that DeSantis has raised a lot of money, but most of it is from big donors. So here's former Wisconsin Gov. Scott Walker, a 2015 presidential hopeful. He was on Fox's "America's Newsroom" last week with some advice for candidate DeSantis. Here's what he said:

SCOTT WALKER: Much of that fundraising haul has come from higher end donors, meaning they either have or will soon hit their maximum. So to shift, they need to be lean. And at the same time, he needs to go bold. I know this firsthand, just having a great track record as governor is not enough, particularly when you go head to head with someone like Donald Trump. And so he needs to kind of light of fire with primary and caucus voters with some really bold ideas that will not only help him in the polls, but ultimately helping with the fundraising at the lower dollar level, which is what you need these days to sustain a campaign.

BROOKS: So Alex, talk a little bit about that. What are donors saying now in terms of where Ron DeSantis is?

CONANT: Well, donors want a winner. And I think he attracted a lot of major dollar support and excitement after his big mid — after his big election last November. And his first quarter fundraising report was very impressive if you just look at the major dollars. I mean, he raised more than in the last six weeks, he raised more money than Donald Trump did, which is really impressive. And he has a lot of major donors who are now invested in his campaign, who are going to go out and try to raise more money from their friends and neighbors to support the campaign. If — and this is an important if — if they continue to believe that Ron DeSantis is a good investment. And that means that they really wanna see momentum.

I don't think the polls matter at all right now, except when it comes to fundraising. If you're lagging in the polls, the fundraising gets harder and harder, and as the fundraising gets harder, it becomes harder and harder to, you know, run an effective campaign. And you kind of get sucked into this death spiral that when I worked on Tim Pawlenty's campaign, that's what happened to us. Scott Walker knows it very well. I don't think Ron DeSantis is near that point right now. But if the fundraising dries up, if his poll numbers continue to go south, I think a month, two months from now, his problems could become more acute.

I don't think we're there, I'm not predicting that. But that is the ultimate, that is the gravest fear, I think, of his campaign.

BROOKS: Right. And so the campaign is talking about resetting now in a number of ways. I mean, I think one of the things they're talking about is to try to make — to have DeSantis focus less on what happened in Florida and more on what needs to happen nationally as one example of the reset.

Tim, what would a reset look like in your view — to make this campaign, you know, pick up some steam and have some new energy?

MILLER: Yeah I don't — I kind of reject Scott Walker's view that he needs to come out with some bold ideas to try to raise money. I think DeSantis' been trying to do. That's what all of his kind of far right policies that he's put out in the spring, you know, were intended to do. And that didn't work.

I think sometimes we overstate in these campaigns, in the presidential campaigns, how critical the money side is. Donald Trump won in 2016 just on earned media with an airplane that had a golf caddy and a PR person and a campaign manager who is, you know, not from the top of the strategic list, right? And so he won through the energy of his own candidacy, through how he resonated with voters.

Like Ron DeSantis has to — is not gonna win this based on TV ads. You know, people already really know Donald Trump. Like, he needs to get out there himself and offer to these voters a view about why he's a better bet, you know, to deliver the policies that they want. And to beat Joe Biden. And right now, he's failing on both counts. I think they're looking at him and saying, "This guy is not actually better to beat Joe Biden. We thought he might have been in the midterms but his campaigning style seems weak. You know, the types of issues that he's running on seem unpopular."

And so I think he has to try to get back to that message from December about how he's a better, you know, a better option to beat Joe Biden. And I think worrying about what big donors are doing in order to fund TV ads is like, is not the path back to winning in a Republican primary.

CONANT: Yeah --

BROOKS: Interesting. Yeah, go ahead, Alex.

CONANT: Yeah, I completely agree with that. I mean, when I worked for Marco Rubio, we spent the entire summer of 2015 trying to raise as much money as we could to raise a bunch — to run a bunch of TV ads in the key states. And at the end of the day, as Tim pointed out, Donald Trump was spending that whole summer on TV and campaigning and gaining in the polls. And that proved to be much more important.

So I do think that the amount of money that you're raising can grossly be overstated. When I see stories about how Ron DeSantis' super PAC has $100 million. Look, there was a candidate who ran eight years ago who had a super PAC with $100 million in it, too.


CONANT: And it didn't do him an ounce of good. I really think --

MILLER: (LAUGHS) Yeah. I remember that candidate. I was working on that campaign.

CONANT: (LAUGHS) Yeah, yeah. Sorry!

BROOKS: Right. So we're talking about Jeb Bush just to bring everyone into this inside moment here.

CONANT: Correct.


BROOKS: Go ahead.

CONANT: I also think. A classic mistake that governors in particular are prone to make — and I think Jeb made this, when I worked for Tim Pawlenty, this is back in 2011, 2012, we made this mistake. They tend to focus on what good governors they were. And when you're running for president in Iowa and you're trying to woo Iowa voters or New Hampshire voters, they really don't care what a good governor you were in whichever state you're from.

They — presidential campaigns are all about the future. They want to know: A, can you beat the Democrat you're gonna be running against, and B, what kind of president are you going to be? What policies are — what are your policy priorities going to be? And so I agree with Tim. I think too much of Governor DeSantis' campaign so far has been backward-looking, talking about Covid, talking about Disney, talking about his record as governor, and very little about what a DeSantis presidency would actually look like.

And I think that is one of the things that they're going to need to pivot towards to get people more excited about his campaign, to make it more about the future and to sharpen the contrast with Donald Trump.

BROOKS: Right. Interesting. So big if: I mean, let's assume DeSantis does right this ship and somehow gets past Trump, either because he beats him or Trump just isn't there because of his many legal challenges. What does a DeSantis-Biden contest look like in, in your view, Tim?

MILLER: Yeah, I think DeSantis will have a strong contest on age, and I think that he'll try to make it a generational campaign. I think the big question is, for DeSantis, is there are two groups of voters. Can he win back the suburban college educated voters that have left the Republican party in droves during the Trump years? And that, you know, were key to, you know, not only Joe Biden's win in 2020, but the wins in the senate races in the midterms like Mark Kelly in Arizona, for example, and Fetterman in Pennsylvania and the Georgia Senate race as well?

And the other question is: Does he lose ground with any of the MAGA voters who have come into the party because they just liked Donald Trump and they just like his affect and the cultural issues? So that would be the big — those would be the two big groups that would swing a general election contest. And the question is: Could DeSantis generational message appeal enough to those groups in order to allow him to do better than Donald Trump did versus Joe Biden?

BROOKS: Yeah. What do you think, Alex?

CONANT: Yeah, look, I think if it's Biden versus Trump, it's a choice. Do we want to stick with what we've got or do we want to go back to Donald Trump? Because everybody knows what a Donald Trump presidency would look like. I think if it's a lesser known or a first term candidate, like a Ron DeSantis, it becomes much more of a traditional referendum on an incumbent president: Do voters wanna stick with Biden for another four years or do they want something different?

I think arguably, if you look at the poll numbers right now, that is a much tougher contest for the Democrats, simply because the president's approval ratings are so low, especially with independent voters. And I think there would be a real opening for a fresh face like a Ron DeSantis.

You know, that said, it's really hard to beat an incumbent president. The economy seems to be — we're a ways out — but the economy seems to be trending in the right direction, which can help an incumbent. So I think it's, you know, I think it's hard to kind of predict this far out.

But I think it's a very different race if it's Biden versus DeSantis or Tim Scott or any of the other Republicans versus a Biden versus Trump, which I think is in part why, you know, secretly the Democrats are really kind of crossing their fingers and hoping that Donald Trump prevails here. Because they think they know how to beat — they believe that they know how to beat him. They think in some ways that would be an easier contest for President Biden.

BROOKS: Alex, let me stick with you for this next question. I'm interested in the other contenders, whether it's Nikki Haley, Mike Pence, Tim Scott, Chris Christie. I know there are a whole lot more Republicans out there as well, but who in this group stands to benefit from a weaker DeSantis?

I mean, let's say DeSantis doesn't reset, can't figure out how to get his campaign sort of back on track. Who benefits the most?

CONANT: Well, I — it's probably Donald Trump at this point.

BROOKS: Yeah, sure.

CONANT: Simply because you know, he — Donald Trump isn't gonna beat get beat unless the opposition can consolidate around somebody. I think six months ago, it seemed likely that the opposition was gonna consolidate around Ron DeSantis. Hasn't happened yet. And if three months from now, DeSantis is floundering, clearly, I think that is probably most helpful to Donald Trump.

But to directly answer your question: Look, Tim Scott, who supported Marco Rubio in 2016, I got to know them. He's a very — he's just a good guy and very authentic, which I think is what voters want, clearly. I think there's a lot of major donor excitement around Tim Scott recently. You see him moving up in the polls in the Iowa and New Hampshire.

I think he's one to watch. I think if Ron DeSantis, you know, continues to move down in the polls that will likely accrue to Tim Scott's benefit. And I think Tim Scott's gonna have a moment. When a lot of people are gonna think, "Is this the guy that could beat Donald Trump?" Whether he can seize that moment or not is anyone's guess, but I think Tim Scott's certainly someone to watch.

BROOKS: What do you think, Tim? Tim Scott? Of course, U.S. Senator from South Carolina, African American. Is he the one to watch?

MILLER: Yeah. I don't think so. I have an article in The Bulwark on this subject just this morning, actually. But I agree with Alex's first answer. I think it's most likely to benefit Trump.

The MAGA voters — You can't win with just the college-educated, Wall Street Journal class Republican voters. It's not enough to win. You have to bridge that and some of the MAGA voters. They thought that DeSantis could do that. Tim Scott, I just do not see as having any appeal with the non-college MAGA voters. The only other wild card in the field, this guy Vivek Ramaswamy, I would suspect that he's gonna do better in Iowa than Scott or Haley or Pence.

BROOKS: And Tim, is there time? I mean, we've got, what, six months to go before the first nominating contest — plenty of time for DeSantis to right this ship, right?

MILLER: I think so. I don't — there's some that wanna just throw dirt on him. And I guess we've been talking about how bad the campaign's been this whole hour. But I do think that if the Republican voters were gonna turn their eyes to somebody, if they decided very late in this campaign that Donald Trump just was not electable because of his legal woes or because of an exogenous event, I think DeSantis remains the most likely person that they turn to.

But he — there's just no doubt that he's lost a lot of ground and that the strength of that argument has weakened substantially since the winter.

BROOKS: Right. And Alex to you on that question. What's the --


BROOKS: Yeah, go ahead.

CONANT: I have flashbacks to eight years ago right now when I was working for Marco Rubio's campaign. And similar things were being said about us as are being said about DeSantis right now. You know, we were going, heading the wrong way in the polls. Our fundraising was less than impressive. Our path to victory was not clear. And we didn't win. (LAUGHS) So to be clear, we didn't win. But we did come pretty close.

We, you know, we surprised people in Iowa. For a short while there, we were winning New Hampshire until we had a bad debate performance, but found our footing and Marco came in third in the overall delegate count. And, you know, I think, had a couple things gone differently at some key moments, you know, may have had a chance to knock out Trump.

So all to say, six months is a really long time in presidential politics. I don't think — Ross Douthat had a very good column in yesterday's New York Times that I would recommend people read. Basically outlining how, look, DeSantis can have a bad month, a bad three months, a bad six months, but if he's left standing come the Iowa caucuses, you shouldn't count him out. And I think that's right. I think we're just a long way out from people actually voting.

BROOKS: All right. Yeah. Six months is many lifetimes in the world of politics. So I agree with that final thought.

Alex Conant, Republican strategist and founding partner at Firehouse Strategies talking to us from Washington, D.C. Thanks so much for being with us today. We really appreciate it.

CONANT: Thank you.

BROOKS: And Tim Miller, longtime Republican political operative, and now writer at large for The Bulwark and co-host of The Next Level podcast. Tim, it was great having you. Thank, many thanks.

MILLER: Hey, thanks Anthony.

This program aired on July 24, 2023.


Stefano Kotsonis Senior Producer, On Point
Stefano Kotsonis is a senior producer for WBUR's On Point.


Anthony Brooks Senior Political Reporter
Anthony Brooks is WBUR's senior political reporter.



More from On Point

Listen Live