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Ron DeSantis' long-haul strategy against Trump comes into view

Although he hasn't yet announced a presidential bid, the Florida governor's team has already had internal discussions about delegate strategy.
Florida Gov. Ron DeSantis.
Florida Gov. Ron DeSantis.Elijah Nouvelage / AFP - Getty Images

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.

“There have been multiple conversations about delegates and how they are picked in various states across the country,” a DeSantis adviser said. “One thing that we have looked at is that Trump can be beat on the delegate portion of all this. He has never been good at that.”

Another DeSantis political adviser said there have been internal conversations about delegate strategy. Staffers expected to lead the effort include Ryan Tyson, a longtime Florida GOP pollster who played a crucial role in DeSantis’ 19-point re-election victory last year, and Jeff Roe, a longtime Republican operative who led Sen. Ted Cruz’s 2016 presidential campaign and is now advising the pro-DeSantis super PAC Never Back Down. 

“I think if you look at out-of-state travel, it’s all over,” this person said. “It’s not missed on anyone there that it’s often to early states or large delegate states.”

A spokesperson for DeSantis’ team declined a request for comment. 

DeSantis, who isn’t expected to formally declare his candidacy until May or June, isn’t expected to skip the first contests. Still, the strategy carries risks: Advanced attention to states that award more delegates under winner-take-all rules later in the primary season could translate into less time in the all-important first nominating contests, allowing Trump or another contender to develop unstoppable early momentum. 

The early stages of the approach are evident in some of DeSantis’ travel this year.

Through Wednesday, DeSantis had attended more than a dozen events outside Florida. Only three — two in Iowa, one in Nevada — were in states expected to hold one of the first four caucuses or primaries. His first trip to New Hampshire is set for next week, a day after he gives two speeches in Ohio.

Some of the states DeSantis has visited, like California and New York, both of which have become specific focuses for the campaign’s early efforts, are home to big donors and delegate hauls. Others, like Georgia and Pennsylvania, also have the benefit of being general election battlegrounds.

“If you’re somebody like me who believes there’s the possibility that 2024 has the makings for a convention-decided nomination, with candidates each having several constituencies and several levels of regional support, it makes sense to be campaigning — or all but campaigning in the case of Ron DeSantis — in these big blue states or these big purple states,” said Dennis Lennox, a GOP consultant in Michigan, where DeSantis has two stops scheduled Thursday.

DeSantis allies note that his travels are related to an arranged book tour and to invitations he has accepted from local GOP leaders who recognize his ability to draw large audiences and raise money for their organizations. DeSantis raised more than $200 million during his 2022 re-election campaign, the most of any gubernatorial campaign in U.S. history, and he is expected to have the largest war chest of the 2024 GOP primary field.

But DeSantis’ itineraries stand in contrast to those of his would-be rivals. While Trump has visited early states sparingly and staged his first big 2024 rally in Waco, Texas, former Vice President Mike Pence, former Ambassador Nikki Haley and Sen. Tim Scott, R-S.C., are among the candidates and likely candidates heavily focused on early states. 

Two pro-DeSantis super PACs have taken the lead as he travels the country, one of them, And To The Republic, often coordinating event logistics and the other, Never Back Down, engaging in polling and other efforts to promote him on the ground. The latter group is led by Ken Cuccinelli, one of the architects of Cruz’s strategy to wrangle delegates away from Trump ahead of the 2016 Republican convention. Never Back Down is expected to operate with DeSantis’ blessing — an important signal to party donors and activists — after he launches his campaign.

Advisers to the group declined to respond to questions this week about whether there are specific plans to shore up delegates for DeSantis. But one official, who requested anonymity to share internal thinking, acknowledged the benefits of a methodical state-by-state approach. National polls showing Trump with double-digit leads are irrelevant, said the official, who pointed to data showing more competitive races not only in states like Iowa and New Hampshire but also in Georgia.

“If he runs for president, Gov. DeSantis is going to win the nomination because of this grassroots support you’re seeing right now in all of these states that he is crisscrossing to,” the official said. “We’re the movement, the voice to get him to run. That’s what you’re seeing in these states. That’s what’s getting missed in trying to see the trees through the forest.”

Thursday’s schedule is particularly illuminating. Haley is set to rally in South Carolina, where she was once the governor and where White House dreams can be fortified or fumbled early in primary season. DeSantis is in Michigan, where Republicans aren’t yet sure when or how they’ll pick a favorite for president. The state’s primary was moved to February to accommodate a Democratic plan to make Michigan an early carve-out state. But the move didn’t comply with the Republican National Committee’s rules and calendar, so state party leaders are considering a later caucus or state convention to allocate delegates.

“You’re establishing these beachheads in states like Michigan, which has not decided what it’s going to do yet, in the hopes that maybe you can work the refs a little bit and get rules that perhaps might favor you more than another candidate in the race,” said Lennox, the Michigan consultant, who noted that the state’s new GOP chair, Kristina Karamo, won the position against a Trump-endorsed candidate and may feel less loyal to the former president.

State parties have until Oct. 1 to submit plans to the RNC for allocating delegates. In the past, rules have ordinarily required convention delegates to be awarded proportionally in the caucuses and primaries held before March 15. Winner-take-all contests, in which first-place candidates can win all of a state’s delegates, traditionally come later in the calendar.

While there are potential advantages to a broader strategy that values later-voting states, there are also risks. Bigger states can be more expensive to organize and advertise in, and failing to notch an early win in Iowa, New Hampshire, South Carolina or Nevada could shift the narrative of the race and keep DeSantis from having the money and momentum to make a deep run.

“I think if you have the resources to play on the larger playing field and not just focus on the early states, then it’s smart to do so,” said a Republican strategist who has held senior roles in past presidential campaigns but is for now unaligned in the 2024 race. “The caveat is you need to close the deal in the early states first. Gov. DeSantis hasn’t done that yet, so he runs the risk of acting too much like a front-runner when he hasn’t cemented that place yet.”

Much of the strategy for DeSantis is focusing on delegate-rich states like California and New York. DeSantis late last year did an event for the failed Republican gubernatorial campaign of Lee Zeldin of New York, a former member of Congress who is expected to be a top official in the state once DeSantis’ campaign becomes more official. 

“Those states obviously have reputations for being Democratic, but in a GOP primary they have a lot of delegate potential,” said one of the DeSantis advisers who was granted anonymity to speak freely about the thought process. “He has polled really well in California, and we think there is potential.”

DeSantis, however, has had missteps even in states where his team sees potential. During a February trip to Staten Island hosted by the New York State Fraternal Order of Police and designed to highlight his law enforcement agenda, he didn’t reach out to key players in the state’s Republican Party. The move was viewed by some as a snub, even among Republicans in the state who have been supportive of him.

“DeSantis kind of has a reputation here for not playing well in the sandbox,” said a New York Republican who wasn’t invited to the event. “In some states you can go around the state party; not here. There is real power down to the county level.”