As the 2024 Iowa Caucus looms, the political landscape – complicated by the calendar – presents formidable challenges for Florida Governor Ron DeSantis. With Donald Trump appearing nearly unbeatable in virtually every state or national poll, DeSantis’s campaign is fast approaching a critical juncture: a full month of nasty and bitter campaigning in which he finds himself sandwiched between a gloating Trump and a surging Nikki Haley, a looming reality check at the Iowa Caucus, and then what looks like a long and painful stretch of unfavorable early states before Super Tuesday.

Despite the tough challenges, DeSantis has a path forward, but a lot of things need to go his way: the Iowa Caucus, the upcoming 2024 Legislative Session in Florida, and whatever groundwork and organization his previously well-funded campaign managed to invest in and build out before Super Tuesday.

DeSantis can’t look past Iowa

The so-called Hawkeye Cauci looms as a pivotal battleground, one of the few obvious places for his campaign to generate good news that might carry him through the rougher days ahead. That’s because after the January 15th caucus, DeSantis will have to survive a an extremely challenging 50-day span that could easily be the doom of his campaign.

Current polling positions DeSantis as a second-place underdog in Iowa, but the media won’t stop talking about a Nikki Haley surge.  Already, DeSantis knows he’s in for a tough December with an intensification of political hostilities on all fronts – with Trump punching down and Haley punching up – caught in the crossfire where each of his opponents can pour their resources into attacking only him. Meanwhile, he’s got to fight a two-front war, playing offense against Trump and defense against Haley.

The Haley Problem and the Calendar Problem (they are one and the same)

Speaking of defense against Haley, the former South Carolina governor announced a formidable $10 million ad campaign for December that spans both Iowa and New Hampshire, attempting to position her as Trump’s main contender. She has strategically put herself in direct opposition to DeSantis, painting him as a mere obstacle rather than a serious contender. And while she and DeSantis share the same objective – survive until Super Tuesday and get Trump one on one – her path is far simpler than the one DeSantis must tread.

Haley merely needs to survive Iowa in third place. Even if DeSantis completely overwhelms her there, he only gets a day of glory before the spotlight shifts to New Hampshire’s first-in-the-nation primary, slated for the very next week. There, polls have Haley as Trump’s top challenger, and DeSantis? Right now, he’s losing – inexplicably – to Chris Christie.

Those first eight days after Iowa are only the beginning of a long stretch of tough states for DeSantis. After New Hampshire, there’s a brief oddball stopover in Nevada for a February 6th “officially unofficial” primary, where Republicans can vote for non-binding results on Tuesday, and then, two days later, participate in the Nevada GOP’s actual delegate selection caucus.  There, DeSantis seems to be holding a strong second place to Trump.

But Nevada will just be a small blip on the media’s radar as the calendar shifts quickly back to the South Carolina primary – Haley’s home state. And she’s polling well there, as expected.  A strong Haley finish there could juice the media narrative that DeSantis is toast.  After that, a small handful of low-stakes primaries and caucuses dot the calendar, including contests in Michigan, Idaho, Missouri, D.C., and North Dakota. DeSantis needs to finish in a strong second in at least a few of these.

DeSantis’s hole cards

In poker parlance, DeSantis has pushed a lot of chips into the pot in Iowa, and he needs to rake at least a few of them back in his direction on January 15th so that he’s got a big enough bankroll to survive that long stretch between that runs through March 5th. Fortunately for him, he’s holding two strong cards that he can bring to bear at just the right time: the 2024 legislative session and his formidable fundraising earlier in the primary season that – theoretically, at least – should have purchased some ground-game and infrastructure that he can cash in on Super Tuesday.

Florida’s 2024 Legislative Session could prove an ace in the hole for DeSantis to seize the national narrative as lawmakers attempt to tackle hot-button issues at the forefront of GOP voter’s minds. By championing popular conservative causes, he can reinforce his reputation as a decisive leader. This period will allow him to showcase his governance skills and policy successes, contrasting his active role in state leadership with his main rivals, none of whom currently hold office. It’s a chance to turn potential policy achievements into national headlines, resonating with GOP voters seeking strong leadership and clear stances on critical issues.

That said, one challenge he faces is that he’s already moved the needle significantly on a host of hot-button issues, the very resume that put him on the national radar to begin with. For DeSantis and his GOP allies in Florida, he’ll have to tread carefully to make sure he’s fighting legitimate battles, because his naysayers will be plenty – labeling virtually everything he does as mere contrivances for the sake of presidential politics.

Even so, DeSantis will have a natural opportunity to demonstrate to the nation that he’s a real-life governor, actively leading a major state, at the moment when most of America’s Republican voters will be paying attention.  That, combined with whatever payoff he’s due from investments made with his formidable war chest early in the contest, could carry him through what are bound to be some rough media cycles between mid-January and early March.

Back to the poker analogy: DeSantis’s journey to Super Tuesday will require timing, skill, and a bit of luck, all of which will combine to play pivotal roles. His performance in Iowa, the strategic use of the legislative session, and the fruits of his campaign’s early labor (if any) could contribute to his staying power during the toughest stretch of the race. While the path is fraught with challenges, DeSantis’s unique position as a sitting governor and his campaign’s strategic planning could provide him with just enough momentum to survive. It won’t be easy.

His reward if he does?  A one-on-one duel with the man currently leading everyone else by nearly 30 points in the polls.