The Art of Losing: How Donald Trump Made Ron DeSantis

The story of the 2018 Florida governor race.

Prior Entries:

Part I: The first DeSantis campaign for the U.S. House

Part II: DeSantis goes to Washington and his 2016 Senate campaign

Over the period of Ron DeSantis’ career that we’ve covered so far, we haven’t seen him be very good at much. He hasn’t been very good at campaigning. He either didn’t know how to navigate Washington or didn’t care enough to even try. Even as a massive right-wing wave swept over the country, he wasn’t able to position himself in a way to directly benefit from it. If you were to look at this and come to the conclusion that he was a lightweight politician not on track to accomplish anything, well…you’d be right, at least under most circumstances.

The Trump era, however, was not one of these circumstances. And DeSantis did have one skill that, although very limited, would work very well in it.

Throughout his career, Ron DeSantis has demonstrated an uncanny ability to keep track of and align with the bleeding edge of far-right politics. At its best, this tendency has brought him a step ahead of his opponents, allowing him to win elections like the 2012 congressional primary race. Of course, at other points, it has led to unparalleled embarrassments, but that’s a story for another day. In any case, when DeSantis entered the political world of the Trump era, he would have seen a conservative base whose priorities and interests had drastically changed. Like the rest of the country, they were riveted by the ongoing drama of the new administration and were starting to understand politics at large through its comings-and-goings. Everything about a politician’s political identity—their connections, their accomplishments, their record—was now all secondary to the role they were playing in the 24/7 saga of Trump vs. the world. So, throughout 2017, DeSantis would devote all of his energies into finding and playing a recognizable role in this story to Republican voters.

I’m a little split on how much credit I should give DeSantis for this. As grand as it would be to christen him as a maverick, it’s also true that he had been running nationally-obsessed campaigns well before this. And it’s not like he had any other angles to work with. Even after two full terms in Congress, he still wasn’t very experienced and didn’t have any connections. His prospective primary opponent, state Agriculture Commissioner Adam Putnam, was yet another well-known statewide official with a legion of in-state allies. Another potential contender, State House Speaker Richard Corcoran, had similarly deep connections and was planning on running in DeSantis’ lane as the candidate on the far right. Under these circumstances, running a race based on local politics would have been paramount to running a race on his opponent’s terms. Moving the conversation away from that wasn’t just DeSantis’ best strategy: it was his only strategy.

But whether he was brought into it by hook or by crook, once DeSantis began his effort to orient the gubernatorial primary around national politics, he would do it remarkably well. In stark contrast to his half-assery as a member of Congress, DeSantis would storm the right-wing news circuit at a manic pace in an effort to finally make a name for himself. In this effort, he benefited substantially from Florida’s extraordinarily long campaign season. Unlike other states that hold their statewide primaries in the spring or mid-summer, the major party contests in Florida are held in late August, providing prospective candidates with as much time as they need to build up their campaigns. So, when DeSantis’ far more well-prepared opponents made their early announcements—Putman launched in May, and Jack Latvala, the President of the Florida State Senate, jumped in in August—it didn’t give them as much as an advantage as it would have if they race were held in, say, March. DeSantis still had plenty of time to make an impression on the one man that truly mattered.

And things weren’t going all that well for this man. After getting off to the worst start in American history, Trump’s administration would be ensnared less than half a year into its life by the Mueller investigation, which—as easy as it is to forget now—dominated political discussion during his early tenure and drove his approval rating down to historic early lows. In this moment of turmoil, Trump-friendly outlets were desperate for anyone who could spin the situation on his behalf. It would be here that DeSantis’ legal background would, for the first time in years, be a major advantage. With his background as a veteran, prosecutor, and a Congressman, he proved to be an irresistible quantity for right-wing media executives, who would book him to come on and defend Trump every time a new controversy came up, as it often did.

There’s a history of DeSantis’ career that presents this strategy as an ingenious campaign tactic, wherein he reached out to Florida conservative voters by tapping into their new sources of media consumption. Maybe he was trying to do that, but it’s not what happened. Polling companies began surveying the race beginning in mid-2017, and they clearly show us that DeSantis was not on the radar of any actual voter in the state that early on. Rather, he was picking up right where he left off in his ill-fated Senate run, with only single-digit support among the electorate. He needed Trump’s help. He wasn’t going anywhere without it. And eventually, at the end of the year, it would come, although not without (as is often the case with Trump) an obsequious gesture of loyalty.

As 2017 came to a close, the Trump administration was in comically bad shape. His approval was solidly beneath 40%, many of his signature legislative proposals had gone down in flames, and his White House’s political operation was so poor that he was being forced to fly to down to the Gulf Coast on a last-ditch rescue mission to save an alleged pedophile from losing a Senate race in Alabama to a Democrat. It didn’t look like the sort of movement you’d make a big bet on if you were thinking long-term, but at that point DeSantis couldn’t have cared less. All that mattered was that Trump was coming near his home state, which meant that DeSantis finally had a chance for some face time with the 45th President. He’d finally get it when he was invited on Air Force One to and from a Trump rally in Pensacola, Florida.

It’s here where history starts to shift into legend. There are many recollections of this fateful meeting, the same story even from the same person changing with time. DeSantis’ people would tell you that Trump was simply impressed by the young Congressman’s conservative values and outsider record and decided he was the best choice. Trump would have told you that too, until recently. Over the past year or so, he has since declared that DeSantis was a “lousy candidate” who came to him with literal tears in his eyes begging for help, and that he told him that he was so far from behind that he couldn’t win even if George Washington and Abraham Lincoln came back from the dead to campaign for him. But the most accurate telling of it is probably the reporting from the time, which simply said that Trump had a conversation with DeSantis, heard DeSantis pander to him, and then told him, “you’re my guy,” and promised to support him.

Ultimately, the specifics don’t really matter. The end result would be a tweet, posted on December 22nd, 2017, as Trump flew to Mar-a-Lago for a Christmas party. The tweet was only two sentences long. It was likely only published because the President, watching Fox News on his plane, saw DeSantis on a segment towards the end of his flight and was reminded of him. In truth, it wasn’t even really an endorsement at all. All Trump did was say that he liked him.

But ever since he pressed “send,” Florida has never been the same.

Male Makeup

It also wasn’t enough. At least, not at first.