Ron DeSantis' 2024 strategy is a straight-up loser

Waiting never works.

(Ron DeSantis/ Getty Images)

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On Thursday, NBC News reported on how Florida Gov. Ron DeSantis is preparing to run for — and win — the 2024 Republican nomination.

Here’s the key part of the story:

Florida Gov. Ron DeSantis’ team is already plotting out a strategy to run against Donald Trump for the long haul. The plan focuses less on making a quick splash in places like Iowa or New Hampshire and more on outlasting the former president in a battle for Republican convention delegates. 

Even though it’s early and DeSantis isn’t officially a candidate yet, in talks behind the scenes, an expanded map is viewed as one of the keys to victory, three sources close to the governor said.

So, DeSantis’ plan to beat Trump — who, I would note, drubbed a field of qualified candidates for the 2016 Republican nomination — is to, um, outlast him in a delegate knife fight? To not overly worry about the early states and instead get into a protracted land (and delegate) war¹ with Trump for the duration of the nominating calendar?

Whoa boy.

Let me offer a bit of quick analysis right here: This will not work. And, more than that, it suggests a fundamental misunderstanding of the way that GOP nomination fights work. And an ignorance of the recent history of Republican nominations.

Let’s start with that recent history, shall we?

Go back 15 years to the 2008 Republican primary. In that race, former New York City Mayor Rudy Giuliani was widely regarded as the frontrunner for the Republican nomination.

He had near-universal name identification thanks to his stewardship of NYC in the wake of the September 11, 2001 terrorist attacks. He looked, for all the world, like a fundraising juggernaut.² Polls put him in the lead. He was the subject of the majority of discussion and analysis in the race. Giuliani was the prime mover.

There was just one little problem: Giuliani was also widely regarded as a moderate — particularly on social issues — within the party. And that was back when that sort of stuff actually mattered to GOP primary voters.

So, the belief was — at least among Giuliani’s inner circle — that he was a poor fit for the Iowa caucus electorate. Iowa had a habit of rewarding social conservatives in past presidential elections, and the caucus format made it more likely that someone with Giuliani’s past positions would struggle.

The decision was made then to largely ignore Iowa and its first-in-the-nation caucuses. The strategy was simple: Giuliani was ahead almost everywhere else so, by downplaying Iowa’s importance to his nomination strategy, he lessened the impact of the caucuses — buying himself time for bigger states with bigger delegate hauls like Florida.

In a memo outlining the strategy released on New Year’s Eve 2007, Giuliani strategist Brent Seaborn wrote:

As voting nears in the Republican nomination process, our campaign remains convinced that our strategy we have long had in place is right – bold, innovative and designed to deal with the radically different election calendar. While many of the beltway insiders seem to remain committed to the old “Carter/Clinton” approach and have questioned the adjustments we have made to our strategic thinking based on the new calendar, we clearly have a winning plan to secure the nomination in an election cycle unlike any other. History will prove us right…

…Our rivals seemingly have built campaigns based on the old calendars’ strategies — a couple of very early state wins to propel them deeper in to the nomination process. To the contrary, our plan allocates time and resources to the many states which vote a bit later — on January 29 (Florida) and February 5.

When former Arkansas Gov. Mike Huckabee, a prominent social conservative, won in Iowa, Giuliani expressed little concern — insisting that it was all part of the plan. (Giuliani finished 6th.)

“I think we’re in good shape,” he told NBC. “We’re ahead in maybe 16, 18 of the 29 states that are coming up. This was the first one. I think it’s one that, quite honestly, we didn’t expect that we would win. And we didn’t put a lot of resources into it. And now we’ll move on to the others.”

Which, ok. The problem for Giuliani was that it was a looong way — in political terms — to the end of January and the Florida primary. With several key votes stacked in between.

Giuliani placed a distant 4th the New Hampshire primary on January 8. (John McCain won it.) He took 6th in the South Carolina primary on January 19. (McCain, again, won.) Giuliani took 6th place in the Nevada caucuses also on the 19th. (Mitt Romney won.)

By the time the Florida primary came along, the race had turned into a two-way fight between McCain and Romney, with Huckabee still making a case that he was the only true conservative left in the field. Giuliani was nowhere in the conversation.

For all of his much-ballyhooed wait-it-out strategy, Rudy finished a distant 3rd in Florida with a measly 15%.

As the Guardian wrote at the time:

Giuliani waited it out in Florida, assessing that taking the fourth most populous state in the country would outweigh wins in the early small states. He would then bounce forward to claim the other big states, including California, New York and New Jersey, on Super Tuesday, February 5.

But by the time his rivals reached the Sunshine State, they had built up critical momentum, and Giuliani couldn't catch up.

Giuliani dropped out of the race the next day — endorsing McCain, who went on to become the party’s nominee and lose, badly, to Barack Obama.

The lesson here should be clear: There is NO successful strategy that does not start with an early-state win. NONE.³

Nomination fights are hugely momentum-driven. The BEST way to look like a winner is to, um, win. And win in an early-voting state where the attention of the media, activists and the donor class will be focused. A win like that can, literally flip the race on its head — changing the likely outcome in a single night.⁴

Then there’s this: If you want to represent the entire Republican party, you don’t get to pick and choose where you fight. You have to fight everywhere — all at once.

That’s especially true when, like DeSantis, you are considered one of the two people most likely to wind up as the party’s nominee. We are not talking about former Arkansas Gov. Asa Hutchinson here — a long-shot who can try to pick a single state (South Carolina?) where he might have a chance at surprising expectations. DeSantis is one of the major players in this race. And major players play. Everywhere.

The uniqueness of the 2024 Republican nomination fight makes an early win even more important to DeSantis.

The race features a former president who has never conceded that he lost the last election. If DeSantis lets Trump romp through Iowa and New Hampshire, the already-lingering notion that Trump is the inevitable nominee is significantly solidified.

Can you imagine what Trump’s rhetoric would be like if he won Iowa and New Hampshire next year? He’d be calling on DeSantis and everyone else to get out of the race the second he is declared the winner. And the megaphone that Trump still possesses within the media — witness the events of the past few days — would mean he would receive wall-to-wall coverage.

The boulder would already be rolling down the hill fast — and be headed to crush DeSantis long before his delegate strategy even had a chance to work.

But, wait, you say. Trump is currently under indictment for his role in paying hush money to a porn star with whom he allegedly had a relationship as a way to ensure her silence in advance of the 2016 election.

The Fulton County district attorney is looking into Trump’s post-election call to the Georgia Secretary of State urging him to find enough votes so that Trump could carry the state in the 2020 election.

A special counsel is investigating Trump’s handling (and potential mishandling) of hundreds of classified documents that he took with him after leaving the White House.

Given those extenuating circumstances, waiting out the nomination fight might not be such a bad idea for DeSantis! After all, Trump could be under multiple indictments by the time Republican voters start voting next year.

True! But, what have you seen from the Republican electorate (or Trump) this week that makes you think that another indictment of the former president would fundamentally alter the calculus of the nomination fight in DeSantis’ favor?

It’s my belief that the New York indictment changes, roughly, nothing in the fight for the nomination. And I would say that future indictments — if they come — would have a similar effect (or lack thereof).

All of which is to say that DeSantis and his team need to think long and hard about a strategy that puts off wins in early states in favor of a drawn-out delegate fight.

Simply put: It won’t work.

1. Everyone knows to never get involved in a land war in Asia

2. Yes, it’s weird to think of Giuliani, who has sacrificed his reputation at the altar of Donald Trump’s 2020 election conspiracy theories, as a beloved presence in the country. But he was once that!

3. This is also broadly true on the Democratic side. Joe Biden lost in Iowa, New Hampshire and Nevada in 2020 but won a sweeping victory in the 4th early-voting state — South Carolina — which wound up propelling him to the nomination.

4. See Barack Obama winning the 2008 Iowa caucuses. Or McCain winning the 2000 New Hampshire primary. Or Donald Trump winning the 2016 New Hampshire primary.