Ron DeSantis faces unique challenges in his campaign for president. Here’s what it would take to win.

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He’s in. Now what?

Gov. Ron DeSantis has for all practical purposes been campaigning for president for at least two years. Now with the official start of his candidacy, he has to run even harder and smarter.

If everything goes right, and wrong for his opponents, DeSantis could win the 2024 Republican nomination, and the presidency.

Or he could end up as a punchline, with the disastrous rollout of his candidacy on Twitter Spaces the only lasting memory of his ultra-hyped presidential effort.

It’s not easy. There will be multiple ups and downs. And the outcome is a long way off. “This is a marathon, not a sprint,” said David Yepsen, who has chronicled many successful and failed presidential candidates during a decades-long career as a political journalist in Iowa, the state that holds the first voting in the series of Republican presidential nominating contests.

Although DeSantis supporters see him as a unique, innovative and transformative candidate, much of what he has to do is the same as every other successful candidate — all while avoiding the pitfalls that doom most.

“You run like you’re running for county sheriff, but you’ve got to convince people you’ve got what it takes to run the nation,” Yepsen said.

Challenges

DeSantis also faces challenges unique to him and the times.

Campaign style: For all his success so far, including a landslide reelection victory in 2022, he’s less polished at the kind of personal, one-on-one and small-group campaigning that is essential for success in early states in the presidential nominating process.

Donald Trump: He has the complication of how to handle former President Donald Trump, the overwhelming frontrunner for the Republican nomination. There’s no model for how a Republican can successfully compete with Trump; all who tried in 2016 limped away with severe wounds.

“Sharpen your knives for the primaries and see whose blood is all over the floor when it’s done,” said Craig Smith, a longtime national Democratic political operative. “And Trump is a street fighter.”

Expectations: For much of 2022, and continuing today, DeSantis was seen as the leading alternative to Trump. After months of attacks from the former president, he’s fallen in public opinion polls. But he’s still far ahead of all the other non-Trump candidates.

“Governor DeSantis has really let his expectations rise. He isn’t just one of the pack, he’s sort of the head of the pack next to Trump,” said Yepsen, who wrote about politics at Des Moines Register and later hosted the statewide program “Iowa Press” on the state’s PBS stations.

“The history books are littered with examples of leading challengers who don’t make the cut for whatever reason. They peak too early, they stumble, they don’t wear well,” Yepsen said. “He’s set himself up to do well, but he’s also set himself up for a bad showing. What if he finishes third? That’s not going to look good,” Yepsen said.

Early states

The entire endeavor rides on Iowa and New Hampshire. A strong performance in those states — winning or doing better than expected against Trump — could propel DeSantis toward the nomination. Iowa and New Hampshire failure likely dooms his candidacy.

“Those first two states are going to be critical,” said Justin Sayfie, a lawyer-lobbyist with Ballard Partners, who splits his time between South Florida and Washington, D.C. He is also publisher of the online political news site Sayfie Review and was communications director for when Jeb Bush was Florida governor.

“If he can’t win Iowa, everything else becomes harder. If he wins Iowa, everything else becomes easier,” Sayfie said.

The importance of the two states illustrates why DeSantis is making the most conventional possible moves for his candidacy after the unsuccessful effort to show he’s something different by conducting the official launch in a Wednesday night audio-only online conversation with billionaire Elon Musk.

On Tuesday, DeSantis holds a campaign “kickoff” — as opposed to Wednesday’s “announcement” — in Des Moines. He stops in four Iowa cities the next day, then four cities in New Hampshire on Thursday and three in South Carolina on Friday.

“He’s got to follow the calendar. That’s what everybody who gets involved in any kind of primary has to do,” Smith said. “If he doesn’t get through Iowa and New Hampshire, he’s probably not going anywhere.”

Now a Broward resident, Smith was the White House political director for part of Bill Clinton’s presidency and was a senior adviser to Ready for Hillary, the super PAC that began organizing efforts for Clinton before she officially became a candidate for the 2016 Democratic presidential nomination.

South Carolina, which has been third in line, can also play an outsize role. In 2016, former Gov. Jeb Bush immediately ended his campaign the night he finished in a distant fourth place in the Republican primary. Its role in 2024 is unknown, since two home-state candidates, former Gov. Nikki Haley and U.S. Sen. Tim Scott are seeking the Republican nomination.

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Retail campaigning

DeSantis has demonstrated an ability to excite Republican voters with his relentless attacks on opponents, the news media, and ideas the conservative base doesn’t like, illustrated by his resounding reelection victory last year in which he won 59% of the vote.

But campaigning in small states such as Iowa and New Hampshire is nothing like campaigning in a giant state like Florida, with 10 different media markets, and where he had the ability to marshal the resources of state government to command constant attention.

Florida has seven times the population of Iowa and 16 times the population of New Hampshire.

“It’s a different type of scrutiny that voters give in those smaller states, and they have an expectation that they’re going to get to know the candidate on a pretty personal level by the time they have cast their votes,” Sayfie said.

Sayfie, who was among the Bush volunteers who traveled to New Hampshire to campaign on his behalf in the leadup to the 2016 primary, isn’t involved on behalf of any of the 2024 Republican candidates.

“It’s very different from campaigning in Florida,” added Steve Duprey, a former chairman of the New Hampshire Republican Party who headed the national Republican Party’s presidential debates for the 2016 campaign.

Personality

Few question whether DeSantis has the discipline and knowledge to do what he needs to do to win the nomination. But one big unknown is how well the governor, who has a reputation as not being a warm kind of people-person, can effectively engage in the kind of small group and one-on-one conversations needed in those early states.

DeSantis’ May 19 visit to the Red Arrow Diner in Manchester, N.H., an all-but-mandatory stop for presidential candidates, was something of a Rorschach test for political observers. People who like DeSantis viewed it as proof he can mingle with average voters. Critics saw it as proof that he’s an introvert who, at best, is bad at small talk and interacting with everyday people.

The importance of that kind of interaction can’t be overstated. Duprey said the key to success is: talk to everyone, listen to their concerns, connect with people.

“Almost every candidate who’s won in New Hampshire has spent substantial time meeting people in small groups, small town-hall gatherings and taking all kinds of questions from all kinds of people,” Duprey said. “That’s what Governor DeSantis needs to do. It’s very different from campaigning in states where you do large-scale media events.”

Personality matters “a lot” in Iowa, where voters “have a chance to look at people up close and see them up close. They expect debates and town halls. You can’t just do it with TV. Candidates who’ve tried it, it just doesn’t work,” Yepsen said.

“He’s got to be himself. And authenticity is the key,” Yepsen said. Candidates who arrive in Iowa and come across as pretending someone other than who they are end up failing. “You’ve got to be genuine.”

Sayfie scoffed at the notion that DeSantis’ interpersonal skills will hinder him. “It’s silly … to hear people question his ability to campaign and connect with voters,” Sayfie said, adding that DeSantis’ Florida victories show he can connect with many different kinds of people. “You cannot win an election in Florida without being able to communicate with the different constituencies that exist in a diverse state like Florida.”

Trump factor

Winning the nomination requires a coalition of support from Republican primary voters who love Trump and those who want to move on to someone else, either because they don’t like the former president’s style or policies, or think it would be difficult to win the November 2024 election against President Joe Biden.

“Navigating messaging on Trump in terms of how to appeal to Trump voters and non-Trump voters alike, that will probably be the biggest challenge from a communications perspective,” Sayfie said.

The quandary: If DeSantis criticizes Trump too much, he risks alienating Trump fans. If he doesn’t criticize Trump, that allows the former president to continue tearing down DeSantis. Trump bombarded DeSantis with criticism on personality and policy in recent months — and that’s been followed by Trump going up in national public opinion polls and DeSantis going down.

“The challenge for DeSantis is he wants to get the Trump voter without crapping on Trump. Right now it looks like he’s trying to be Trumpier than Trump as a way to get at [them], so he doesn’t have to go negative on Trump. But at some point he will have to make that decision,” Smith said. “If he survives long enough, he will have to draw a sharp contrast between him and Trump.”

In the leadup to the official announcement, DeSantis generally avoided responding to Trump’s attacks and didn’t directly go after the former president. That changed on Thursday, DeSantis’ first full day as an official candidate. During a series of appearances on conservative media outlets, he criticized Trump on fiscal matters, immigration and the COVID-19 pandemic.

The delicate maneuvering is even trickier because of DeSantis’ history of flattering and championing Trump when he was president. DeSantis’ defense of Trump during appearances on Fox put him on the then- president’s radar. And Trump’s endorsement of DeSantis propelled him the 2018 nomination for governor and general election win that fall.

In one interview on Thursday, DeSantis said Trump had changed. “I don’t know what happened to Donald Trump.”

On his Truth Social online platform, Trump continued to knock DeSantis on Thursday. “When the Ron DeSanctimonious facts come out, you will see that he is better than most Democrat governors, but very average, at best, compared to Republican governors!”

How should DeSantis handle Trump? People “will respect a candidate who draws distinctions, but they have to sort of like a candidate first,” Duprey said. “If the election were held today, President Trump would win New Hampshire by a comfortable margin. So I do think Governor DeSantis will need to draw contrasts, but before he does that too directly, he’ll need to establish a base of familiarity here.”

Message

DeSantis has built his national name — the PBS NewsHour described him as “a headline-generating machine” — by championing conservative, and sometimes far-right, positions on many issues. With the support of a pliant state Legislature, he’s been able to sign into law a range of policies on abortion COVID, education, LGBTQ issues, regulating businesses, and immigration.

That could be positive in Iowa which, like many other states in rural America, has moved considerably to the right in recent decades. Rural America “is just getting redder,” such that middle-of-the-road or slightly left-of-center candidates can no longer get elected in places where they were successful a generation ago.

So things like signing a ban on almost all abortions in Florida after the sixth week of pregnancy could play well in Iowa.

Still, Yepsen said, “There is a concern, even among a lot of Christian leaders, social conservatives, that you’ve got to do more than just out-conservative the next guy. It’s going to take more than just a strong anti-abortion position.”

Yepsen said DeSantis’ anti-woke brand isn’t enough. “It’s important, but it’s not the whole game. He’s got to have something else.”

It could be even tougher in New Hampshire, Duprey said.

Duprey said New Hampshire is a libertarian state where people don’t like the government telling them what to do, and polling shows many voters favor abortion rights.

In New Hampshire, the primaries are open to undeclared, or independent, voters, Duprey said. As it stands, Biden faces no serious opposition for the Democratic presidential nomination, giving people less incentive to vote in that state’s primary.

Duprey said there is a portion of voters who are “very concerned about social issues.” But, he said, not likely a big enough percentage to win a primary. “Remember, the largest party is undeclared voters.”

“It’ll be interesting to see whether independent voters who can walk in and take a primary ballot that day and tend to be more moderate on social issues can accept or not make it a major issue, the new Florida law, which is more restrictive certainly than New Hampshire has.”

The other challenge, Smith said, is not running far enough to the right that DeSantis turns off moderate Republicans. He, as well as many Republicans, said there’s a post primary danger for someone who goes too far to an extreme to win a party nomination. “You can’t make yourself so toxic in the primaries that you make yourself unelectable” in the fall.

Money, endorsements

Money: DeSantis has been amassing campaign cash during his time as governor, and has donors lined up to give more and raise even greater sums from their contacts. The money is a significant advantage, but people who’ve been involved in campaigns said it’s not the most important factor.

Sayfie said DeSantis would have plenty of money — although, he said, it’s not the most important factor. “You don’t need a lot of money to win the primary if you have the right message,” Sayfie said.

Endorsements: The Florida governor has also received endorsements from local political leaders and elected officials in both early states. “On the plus side, he’s picked up some good endorsements from legislators, and nuts and bolts people. He’s got good strategists working for him. I think he’s doing that right,” Yepsen said.

Smith said the local supporters, including state legislators DeSantis has in Iowa, are important. “That gives him a foot up.”

Anthony Man can be reached at aman@sunsentinel.com, on Twitter @browardpolitics and on Post.news/@browardpolitics.