Ron DeSantis’s Problem Wasn’t Criticizing Trump Too Much or Too Little

Left: Former president and Republican presidential candidate Donald Trump campaigns in Mason City, Iowa, January 5, 2024. Right: Florida governor and Republican presidential candidate Ron DeSantis visits the border community of Eagle Pass, Texas, June 26, 2023.

Critics of DeSantis’s campaign underestimate the challenge of courting Trump supporters.

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Critics of DeSantis’s campaign underestimate the challenge of courting Trump supporters.

R on DeSantis insists that his presidential campaign will continue after Iowa; he told Hugh Hewitt this morning that he’s in the race through March. But with a make-or-break stand in the caucuses that broke — a 30-point loss to Donald Trump amidst disastrously low turnout — things have not gone as planned for the Florida governor. It’s time to look back on what went wrong for a campaign that stood at 30 percent in national polls two months before DeSantis announced his bid.

There’s a perennially roiling debate over DeSantis’s criticisms of Trump: Did he criticize him too little? Too much? On the wrong grounds? In the wrong venues? But the critics have it easy — they don’t have to actually win votes.

The Uphill Battle

I start with two related premises. First, the unfortunate reality: It may be that Donald Trump wasn’t and isn’t beatable. I thought he was, and so did many others, but there was always only one way to find out. It’s not over yet: Nikki Haley has banked her shot on New Hampshire (where polls show a closer race with Trump than the Iowa polls did) and South Carolina (her home state). DeSantis even insists that he can still win, although I’m at a loss to see how that happens unless Trump exits the race.

Trump has been running as a de facto incumbent given his status as ex-president and two-time nominee. His support has remained stubbornly impervious to an endless parade of things that would have killed any other politician’s career. He took a hit in the polls after his disastrous impact on the 2022 midterms, dropping in the RealClearPolitics average from over 50 percent with Republican voters to a low of 43 percent on March 10, 2023. But from the moment Alvin Bragg dropped the first of four indictments against Trump on March 30, the ex-president surged, hitting 54 percent by April 20 as Republican tribal instincts and anger at a weaponized justice system overwhelmed all reason and sentiment. Trump has never looked back. That was a month before DeSantis entered the race on May 24.

That doesn’t mean DeSantis shouldn’t have run. You can’t know what’s possible in a campaign until you try. Just ask dark horse Jimmy Carter about 1976, or recall Bill Clinton getting into a 1992 race while George H. W. Bush was riding high and Mario Cuomo was expected to clear the primary field, or consider Barack Obama deciding he wasn’t going to wait and defer to Hillary Clinton in spite of her powerful front-runner status and famous vindictiveness. Far more people have regretted missing their moment in presidential politics than have ever regretted running too soon when the stars seemed to be aligning for them. In fact, it was once conventional wisdom that Republicans needed to run and lose before the primary voters would consider it their turn: Ronald Reagan, George H. W. Bush, Bob Dole, John McCain, and Mitt Romney all came back to win the nomination after a prior primary loss (or, in Dole’s case, on the third try).

Trump aside, this was as good a moment as DeSantis could hope for. George W. Bush was elected president two years after a thumping reelection to a second term as governor; so was Franklin D. Roosevelt. The scale of DeSantis’s success in 2022 and the fact that his national reputation was tied to an event (the Covid pandemic) that was apt to fade fast in short memories were both arguments in favor of striking while the iron was hot. People who routinely criticize elected Republicans for lacking the courage to stand up to Trump are the last ones who should fault DeSantis for having the guts to take his presidential shot straight into the teeth of Trump’s popularity with the party.

The Unsolved Riddle

My second premise: Even if Trump is beatable by a Republican, nobody has yet done it. It’s presumptuous for commentators to just throw around alternative strategies as if they were easy and obvious. If there’s a magic formula for the right frequency and degree of criticizing Trump, we don’t know what it is. We should all have some humility in approaching the question of what was and wasn’t possible for DeSantis.

Ted Cruz got closer than anybody has so far: He beat Trump in eleven contests. After his victory in the Iowa caucuses, Cruz’s wins over Trump included a 55-point win in Utah, a 24-point win in Kansas, 17-point wins in Texas and Idaho, and 13-point wins in Wisconsin and Maine. Those represent the bulk of Trump’s 15 losses in 2016 (Marco Rubio won three contests, and John Kasich one).

On the specific issue of how to criticize Trump, Cruz tried a bunch of different approaches, from largely ignoring Trump to praising him as “terrific” and blaming the media for asking Cruz to be critical to blasting Trump’s “New York values” and taking the gloves off to tag-team Trump alongside Rubio at a debate that was enormously satisfying to watch but ultimately inconsequential. Cruz got under Trump’s thin skin enough to be branded “Lyin’ Ted” and have Trump insult his wife’s appearance, accuse his father of involvement in the JFK assassination, question whether Cruz was eligible to run, and complain that Cruz had stolen Iowa and rigged Colorado.

In the end, while it worked in a bunch of places, it wasn’t enough. Cruz went down trying to keep his dignity at the convention with a call to “vote your conscience,” but he ultimately bent the knee. He has endorsed Trump again in 2024.

This time around, we observed a spectrum of approaches. Chris Christie opened both barrels on Trump and was run off the road. Vivek Ramaswamy went to the other extreme, ran as an obsequious toady to Trump, and dropped out of Iowa after finishing with 7.7 percent of the vote, double digits behind both DeSantis and Haley. Only in one poll in the whole race did he reach 10 percent in Iowa; he withdrew while polling at 4.3 percent nationally.

In other words: Anybody telling you they know what DeSantis should have done to win is guessing.

Mistakes Were Made

All of that being said, and aside from the specific question of attacking Trump, we can reject some of the overplayed critiques of DeSantis and his strategy without pretending that his campaign was flawless. There were unquestionably some bad decisions along the way, some of which were apparent at the time and others of which are clear in retrospect — and while the governor’s advisers bear some of the fault, at the end of the day it’s the candidate’s responsibility to get this stuff right. Eight examples, small and large:

  1. DeSantis failed to heed Scott Walker’s public advice from his own experience: Talk about what you’re going to do, not just about what you’ve done. Running only on his tremendous Wisconsin record didn’t do it for Walker. DeSantis has rolled out quite a few detailed policy proposals, but he never really captured the public imagination with a signature proposal like Trump’s “Build the Wall” or Bush’s tax cut. To this day, the core of his message is still Florida.
  2. DeSantis got burned whenever he tried to find a middle ground. His position on Ukraine, while arguably at the center of the party, has proven rhetorically a lot weaker than the pro- and anti-Ukraine poles, as Haley and Ramaswamy have shown.
  3. DeSantis should have engaged with the national media from the beginning. He spent the crucial first few months of the campaign avoiding the press. That strategy had worked for him in Florida to some extent (although he seemed to have forgotten how much his stock had risen from having fought with reporters at press conferences during the pandemic). He’s good at going into the lion’s den of hostile press venues. That plays to his strengths (discipline, command of details) rather than his weaknesses (lack of humor and warmth).DeSantis realized too late what he was missing and changed course. He told Hewitt this morning, “I came in not really doing as much media. I should have just been blanketing. I should have gone on all the corporate shows. I should have gone on everything. I started doing that as we got into the end of the summer, and we did it. But we had an opportunity, I think, to come out of the gate and do that and reach a much broader folk.”
  4. DeSantis also didn’t take a broad enough view of conservative media, especially sources (including but by no means limited to National Review) with voices who were largely on his side but occasionally critical. People who are 70 percent or 80 percent or 90 percent friends are not enemies. There’s a reason why DeSantis never sat down for an interview with me or anybody else at National Review — even Ramaswamy did that. It’s not that we have an enormous audience by ourselves, but talking to random New Right “influencers” while declining to talk to established voices in the traditional conservative movement is how you end up losing a lot of old-line, Trump-skeptical Republican voters to Haley. Many such voters were open to DeSantis so long as they thought he was the strongest alternative to Trump, but, when he ignored them, they drifted away as they no longer felt the need to compromise with DeSantis’s populism and social conservatism. DeSantis has a lot to offer to traditional Reaganites, but not if they feel that he’s blowing them off.
  5. Launching on Twitter was a dumb gimmick. It was glitchy, had no visuals, descended quickly into a wonky, niche conversation, produced more bad press than good, and suggested that DeSantis didn’t understand where the primary-voter audience was.
  6. He hired some too-online people, to his detriment. You can’t beat Donald Trump by out-meme-ing him, and in the attempt you’ll likely end up aiming for micro-audiences that are more trouble than they’re worth and having to fire people who embarrass the campaign in the eyes of normal voters.
  7. One of the dumber unforced errors, from which DeSantis had to retreat, was his embrace of RFK Jr. Sure, his populist, vaccine-skeptical audience overlaps to some extent with that of DeSantis, and there is some entertainment value to be had in reminding people that the Democrats brook no dissent. But anybody who’s been a Republican for any time has a deep and abiding hatred of the Kennedys that is almost pre-political — let alone a Kennedy with a long track record of far-left extremism and conspiracy theories.
  8. Finally, the DeSantis super PAC simply blew through too much money for too little return and ended up sniping at the candidate down the stretch. This didn’t reflect the same sort of hyper-competent management that we had seen from DeSantis’s running the government of Florida.

Unlike other postmortems, I would never fault DeSantis for taking a principled stand by signing the six-week “heartbeat bill” in Florida, because focusing only on late-term abortions means surrendering ground on the great bulk of abortions. As Noah Rothman details, blaming pro-lifers is a cheap tactic to distract from other self-inflicted electoral wounds. That said, defending a stronger position on life than did Trump and Haley meant that DeSantis was fighting on a lot of fronts, and he wasn’t rewarded for it; some pro-life activists criticized him instead for not backing a federal legislative ban.

Should He Have Attacked More?

The central challenge for DeSantis was always how to peel off people who had voted for Trump in the past two general elections and perhaps even some who had voted for Trump in the 2016 primaries. That’s always the challenge of running against an incumbent: People may sour on him, but if they haven’t, there’s only so much you can do to move them, and you have to do so without telling them that they were wrong to back this guy in the first place.

Again: We don’t know how to do it. Reagan lost his primary challenge to Ford in 1976. Ted Kennedy lost to Carter in 1980. Pat Buchanan got steamrolled by George H. W. Bush in 1992. Even Lyndon Johnson never actually lost a primary in 1968. Nobody in the primary era has defeated an incumbent or a former president.

By my count, four elected presidents have sought and been denied renomination, all in the convention era. The most recent was Teddy Roosevelt in 1912, when he was challenging a sitting president. Before that was Ulysses S. Grant in 1880, and he was undermined by public sentiment against any man serving a third term. Before Grant was Franklin Pierce in 1856, after his policies effectively destroyed his party in the whole northern half of the country. The other was Martin Van Buren in 1844, four years after a blowout loss, when he got on the wrong side of the question of annexing Texas. Two of those four would end up leaving their parties to launch third-party campaigns.

It’s simply untrue, as some of his critics on the center-right would tell you, that DeSantis backed down from a sustained critique of Trump. There were a number of themes that he pressed consistently across stump speeches and interviews: that Trump let Dr. Fauci lock down the country; that Trump failed to build the wall; that Trump would be unable to serve two terms if elected; that Trump was part of a “culture of losing” that is to blame for setbacks in 2022; that nominating Trump would put all of Trump’s legal and political baggage center stage; and, more broadly, that Trump is just too easily distracted and focused on his own dramas to get things done, whereas DeSantis has the discipline and laser focus to deliver on his promises. The latter argument is the closest DeSantis would get to a regularly delivered criticism of Trump’s character — DeSantis tried to make a virtue out of his preference for briefing books and the details of governance over entertaining people.

Harder shots at Trump’s character were occasionally delivered off the cuff but not sustained. For example, in December, he mocked Trump for being a sore loser:

“If Trump loses he will say it’s stolen no matter what. . . . Absolutely, he will, he will, he will try to delegitimize the results,” DeSantis said. “He did that against Ted Cruz in 2016. And he will do that. I mean, even when like The Apprentice didn’t get an Emmy, he said, he said, so I think I don’t think there’s been a single time he’s ever been in competition for something where he didn’t get it, where he has where he’s accepted. I don’t think he will do that.”

Marc Caputo’s big postmortem cites another example I discussed at the time of DeSantis drilling Trump after the Alvin Bragg indictment; Caputo notes that DeSantis didn’t follow it up:

“I don’t know what goes into paying hush money to a porn star to secure silence over some type of alleged affair, I can’t speak to that,” DeSantis said as the audience laughed. “What I can speak to is that if you have a prosecutor who is ignoring crimes happening every single day in his jurisdiction, and he chooses to go back many, many years ago to try to use something about porn star hush money payments, that’s an example of pursuing a political agenda and weaponizing the office.”

As Caputo notes, it was a one-time thing rather than a recurring attack line:

Trump supporters and conservative influencers flooded Twitter with condemnation of what DeSantis said. DeSantis’s political team was caught flat-footed.

“We loved that he said it, but we didn’t know he was going to say it,” said a former staffer. “The blowback was just intense and so we decided to just leave it alone. The idea was to engage with Trump in a thoughtful way, not just trade insults with him.”

DeSantis soon dropped saying “porn star payoff” ever again. “Mr. Never Back Down backs down,” one Trump adviser crowed to The Messenger at the time. “He’s scared.”

The hazard of going after Trump’s character is that it runs the risk of asking voters to implicitly admit that they were wrong to vote for him the first two times. That’s why the more calculated lines of attack focused on convincing voters that Trump was an old, distracted man with a lot of political baggage whose time had passed, who would struggle to win, and who wouldn’t deliver much in office.

But is that ever enough? My general experience with campaigns is that winning candidates are almost always those who attack their opponents remorselessly and relentlessly — those who convince the voters that the other guy is a racist, a pinko, a warmonger, a coward, a crook, a greedy capitalist, whatever. That’s how Trump and Romney treated their Republican primary opponents, and it’s how Barack Obama treated Romney and McCain.

A fairer critique would be that the DeSantis attack lines just weren’t visible enough: He didn’t build ad campaigns around them, and on the national debate stage, he was as apt to defend Trump as he was to attack him. It’s hard to attack a guy who isn’t onstage, but until he got one-on-one with Haley, DeSantis didn’t really attack the others, either; he treated the debates as a chance to push his positive message. That looks now like a missed opportunity. If you’re asked a question that calls for even a qualified defense of your opponent, you should never miss the chance to remind the audience why your opponent is bad.

Should He Have Attacked Less?

The opposite theory is that DeSantis should never have criticized Trump at all; he should just have waited, meekly and passively, for Trump supporters to stampede to him because they are too easily offended and plug their ears when somebody says anything against Trump. John Daniel Davidson at the Federalist offers the most pristine version of this theory in a column titled “Ron DeSantis Failed Spectacularly in Iowa, But It Didn’t Have to Be This Way”:

Every [DeSantis] decision was about comparing himself to Trump in the most explicit and unhelpful ways. Ever since he announced his candidacy, DeSantis has been obsessed with taking on Trump, never missing an opportunity to malign the former president or take a cheap shot, even when it was unnecessary or frankly irrelevant to whatever he was talking about.

Leave aside just how disconnected from the reality of the DeSantis campaign this is. Leave aside Charlie’s critique of what this column says about the mind-set of Trump defenses. Davidson attributes DeSantis’s decision to criticize the person he was running against to the advice of “Beltway vest aficionados and their friends in the donor class,” as if criticizing your opponent is some sort of Washington witchcraft hitherto unheard of in politics. Does Davidson think that DeSantis has made the same mistake by attacking Haley as a tool of the donor class? That Trump has made a mistake with his scorched-earth attacks on DeSantis? Is Davidson unfamiliar with how DeSantis went after Adam Putnam in their primary fight in 2018, calling him “an errand boy for U.S. sugar,” or how every primary works?

Davidson’s alternative prescription is that DeSantis “could have praised Trump’s achievements and defended him from the unfair attacks leveled at him by Democrats, as Vivek Ramaswamy has done.” That would be the same Ramaswamy who dropped out of the race after never cracking single digits and has never in his life won an election. Sure, that guy must be the expert on winning campaigns.

Davidson says that DeSantis “mistook Trump for his main opponent when his real opponent — and the real villain in all this — is the Democrat machine that’s trying not only to take out Trump before November but also to destroy democracy and self-government in this country.” Now, it’s true that primary voters want to see that you can take on the Democrats, so tunnel vision that causes you to forget to take the fight to the other party and the media would be perilous. DeSantis didn’t shy away from taking time during the campaign to debate a leading Democrat on national television. But you don’t get the chance to fight the Democrats if you don’t beat your primary opponents. Davidson doesn’t say that Trump lost sight of his real opponents by attacking DeSantis. To the contrary, Trump’s campaign understands reality: Caputo quotes Chris LaCivita, one of the Trump campaign’s co-managers, saying that “DeSantis never established dominance. . . . If you want to be The Man, you’ve got to beat The Man. Ron DeSantis is not The Man. Donald Trump is The Man.”

That, and not Davidson’s white-glove drawing-room civility, is how campaigns are won and lost. You can’t beat a candidate without conveying to the voters the reasons why they should not vote for him. I realize there is a psychic dynamic that causes people to dismiss all criticism of Trump, but the logical conclusion is simply that people who think that way are just not persuadable voters in any number. How was DeSantis supposed to win them away from Trump when starting off behind? What’s the mechanism? Davidson doesn’t propose any remotely plausible plan that has ever worked in the history of politics.

Maybe that’s the answer: that Ron DeSantis set himself an impossible task. If so, I will always respect the courage required to attempt it.

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