Those who don’t learn from history are doomed to repeat it. Had Ron DeSantis learned from the mistakes made by Donald Trump’s 2016 rivals, he would have run a better campaign (or skipped it altogether).
Instead, it seems likely that DeSantis’ presidential bid will end with his reputation being in much worse shape than when the campaign began. But was this always preordained? Was Trump’s (likely) victory a foregone conclusion? I don’t think so.
However, DeSantis’ campaign, such as it was, went off the tracks even before his official campaign announcement last summer. From where I stand, there are seven main reasons this happened.
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1. Florida taught him the wrong lessons.
DeSantis should have read a business book called, What Got You Here Won’t Get You There. People tend to think what made them successful at one level will make them successful at the next. Often, it doesn’t. In a sense, DeSantis was cursed by his success in Florida.
Rather than forcing DeSantis to improve his weaknesses, his success at the state level allowed him to skate by and avoid doing things he wasn’t good at.
Take, for example, the way he snubbed the “national regime media” (something he now regrets). During his time as Florida’s governor, DeSantis either avoided the mainstream media (and catered to conservative “influencers”), or he bullied them (and used them as press conference props). This worked wonderfully in Florida, but it wasn’t scalable.
Eventually, DeSantis was forced to do interviews with mainstream shows. Honestly, though, he wasn’t great at them, partly because he had little experience learning how to answer questions that he perceived as unfriendly. Protectionism, it turns out, doesn’t work.
2. DeSantis waited too long to get in the race.
In politics, “Speed kills.” You define your opponent before he defines you. You strike while the iron is hot. These clichés became clichés for a reason.
Unfortunately, DeSantis could not call a snap election and try to beat Trump right after the 2022 midterms when his popularity peaked, but he could have aggressively begun redefining Trump. Instead, DeSantis focused on piling up a list of accomplishments during Florida’s legislative session, under the premise that the voters might care about his ability to put points on the board. They didn’t.
On paper, it made sense that GOP primary voters might want a more-competent Trump—someone able to take ideas they already liked and put them into law. When it comes to GOP primary voters, at least, he misread the audience.
Republican presidential candidate Ron DeSantis delivers remarks at the 2023 Christians United for Israel summit on July 17, 2023 in Arlington, Virginia.
Anna Moneymaker/Getty/Anna Moneymaker/Getty3. Like Ted Cruz in 2016, he thought ideological purity mattered.
Today’s GOP primary voters are not persuaded based on conservative orthodoxy. So by tacking to Trump’s right on abortion, for example, DeSantis not only failed to catch fire with primary voters, but he arguably hurt his electability argument, as it pertains to who could defeat Joe Biden. These miscalculations were bound to happen with so many Cruz veterans in the DeSantis orbit (and running DeSantis’ SuperPac).
4. He assumed that Trump would fade and he could inherit his voters.
How many times have Republican candidates rationalized ignoring Trump, based on the assumption that Trump would drop out of the race—or that voters would simply move on from him?
Had DeSantis jumped in the race early and aggressively defined (i.e., attacked) Trump and set the 2024 campaign narrative (i.e., “what this election’s about”) to focus on electability, he might have preemptively framed Trump’s first indictment as a massive blow. For example, DeSantis might have spent months warning that an indictment was coming, and that said indictment would doom Trump’s chances against Biden in November. Instead, he did something even worse.
5. He provided cover for Trump.
It’s not just that DeSantis failed to effectively attack Trump, it’s that he defended Trump from what might have been serious developments. By helping Trump suggest that the indictments were politically motivated and later saying he would pardon the former president, DeSantis contributed to a permission structure whereby Republican voters had every reason to remain loyal to Trump, rather than moving on from him.
Donald Trump and Ron DeSantis at Southwest Florida International Airport October 16, 2020, in Fort Myers, Florida.
Brendan Smialowski/AFP/Getty6. He didn’t shore up non-Trump Republican voters first.
Rather than locking down a coalition of gettable non-Trump Republicans and then attempting to woo soft Trump voters who were ready to move on, DeSantis first attempted to court hard-core Trumpy voters. It’s hard to imagine how or why he thought this would work. On top of that, he took stances (such as calling Russia’s Ukraine invasion a “territorial dispute”) that repelled formerly gettable Reagan Republicans (providing a rationale for Nikki Haley’s candidacy).
7. He bought into the “very online” hype.
Once it became apparent that rank-and-file Trump voters weren’t going for Trump Lite, DeSantis still refused to focus on consolidating the rest of the GOP electorate.
Instead of worrying about the kind of normie voter who might caucus in Des Moines, he focused on the young and highly educated, very online voters (a priority that was reflected in his staff hiring decisions). DeSantis had swerved toward Edgelord territory. This led to weird decisions, such as hosting his official campaign announcement on Twitter Spaces, a move that turned disastrous when the feed crashed for the first 20 minutes (and that was only one of many technical calamities).
Building on his Florida experience (see listicle number 1), he also spent much of his early presidential campaign focused on culture war issues like attacking “wokism,” pushing vaccine skepticism and banning local COVID-19 mask requirements, or going after Disney and calling people “groomers.”
In some ways, DeSantis’ failure to catch fire was predictable. I predicted it in May—months before he officially launched his campaign. But I don’t believe in predestination in politics. The world is dynamic. If DeSantis had started off in Jan. 2023 with the right strategy and message, things might have turned out differently.
While one could argue that DeSantis’ awkwardness or introversion doomed him—or that the indictments made Trump unbeatable by causing Republicans to circle the wagons around him—I believe that a radically different type of campaign strategy might have worked.
At the end of the day, it seems likely that DeSantis’ ego blinded him to some of the realities, stopping him from learning some of the lessons of 2016, and preventing him from doing the things that might have made him the GOP nominee in 2024.
In this regard, Ron DeSantis is a cautionary tale.
