Can Ron DeSantis beat Donald Trump? These Florida political veterans aren’t so sure

He’s a ubiquitous presence in conservative media with a reputation as an anti-woke warrior who has used a compliant state legislature to make Florida a mecca for Trump-era Republicanism.

But if Ron DeSantis wants to be president, he has to defeat Donald Trump and Joe Biden, and prominent Florida politicians aren’t so sure either of those things will ever happen.

The second-term Florida governor, who for months has sojourned through the traditional primary battlegrounds of Iowa and New Hampshire while hawking his manifesto-cum-memoir The Courage to be Free, was once seen as a formidable obstacle to the twice-impeached ex-president’s dream of reclaiming his place in the White House.

But in the weeks since Mr Trump found himself on the wrong end of an indictment from a New York grand jury, the Florida governor has seen his standing in the polls tumble while his fellow Floridian has surged to a commanding lead among GOP primary voters.

Still, Mr DeSantis has launched a presidential presidential campaign that has support from a decent chunk of his party and a formidable war chest transferred from his successful re-election run last year. On 24 May, Mr DeSantis filed paperwork declaring his candidacy.

He gained that support — and a national profile — by winning the hearts and minds of some former Trump boosters through his wholehearted rejection of any and all restrictions or mandates meant to contain the Covid-19 pandemic, and he has kept his core support among some GOP diehards by using a compliant state legislative majority to enact a laundry list of conservative priorities and use resulting culture war battles to raise his profile even further.

A Republican media strategist who worked on Mr Trump’s 2020 campaign, Giancarlo Sopo, told The Independent he believes Mr DeSantis is “the obvious choice” to lead the GOP in next year’s election because of what he described as the Florida governor’s role in enacting “the boldest conservative agenda this country has seen since Ronald Reagan” and Mr DeSantis’ “unique ability to demoralize and defeat the left”.

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Yet Mr Sopo’s confidence in Mr DeSantis’ abilities wasn’t shared by many Florida GOP veterans contacted by The Independent.

None of the Florida-based operatives would speak on the record for fear of alienating the governor, who has earned a reputation for vindictiveness during his five years in Tallahassee.

But the consensus opinion among the GOP political strategists, many of whom have had a hand in national campaigns of years past, was that the governor’s reputation as a lib-triggering prizefighter is a carefully manufactured façade — a recent invention that is a fabrication formed by a coterie of combative press aides and sympathetic media outlets.

Mr DeSantis’ reinvention as a woke-battling colossus standing astride the Sunshine State could not be a starker contrast to how he conducted himself during the five years he spent in Washington while representing Florida’s 6th Congressional District in the House of Representatives.

The future governor won his first House election in 2012, just two years after the Tea Party movement that arose after Barack Obama’s inauguration helped the GOP retake control of the chamber from the Nancy Pelosi-led Democratic caucus.

As he geared up to run in that election, Mr DeSantis found a way to capitalise on the anti-Obama sentiment within the GOP by calling his first book Dreams from Our Founding Fathers ­— a title that positioned it as a response of sorts to Mr Obama’s best-selling memoir, Dreams from My Father.

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After he was sworn in to Congress in January 2013, he quickly became one of the most conservative members of an avowedly conservative House Republican Conference. After he won a second term in the 2014 midterms, he became a founding member of the House Freedom Caucus, a group of far-right Republicans that would become such a thorn in the side of then-House Speaker John Boehner that the Ohio Republican chose to resign rather than suffer the indignity of being forced out for forging one too many compromises with Mr Obama.

The Florida Republican compiled as conservative a voting record as any member of the House GOP, but despite arriving on the scene at a time when his brand of hard-right conservatism was becoming more and more en-vogue in the House, he never became as well-known as some of his equally conservative colleagues, such as Reps Jim Jordan (R-Ohio), Mark Meadows (R-NC) or Justin Amash (R-MI).

One possible reason for that — his reputation as an awkward loner — appears to have already hampered his chances against Mr Trump.

A former House GOP colleague, ex-Michigan Representative David Trott, told Politico earlier this month that Mr DeSantis never once attempted to so much as start a conversation with him during the two years they sat next to each other on the House Foreign Affairs Committee.

“I was new to Congress, and he didn’t introduce himself or even say hello,” he recalled in an email to the outlet’s Playbook newsletter.

In a subsequent phone interview, Mr Trott also called the Florida governor an “a*****e” and said he does not think Mr DeSantis “cares about people”.

Another House colleague who spoke anonymously to NBC News said he “had no friends” in Congress and was “not a backslapping politician”.

“He wasn’t a friendly guy. He was a personal-agenda-driven guy,” said one lawmaker. “I was with him in the gym every morning and could hardly get him to say hello. He didn’t seem like he liked being here.”

Mr DeSantis’ alleged dislike of the lower chamber became evident after just two terms when he briefly stood as a candidate for the Senate seat held by Senator Marco Rubio, who was then running for president in the 2016 primary.

When Mr Rubio lost the Republican primary for president to Mr Trump, Mr DeSantis instead stayed on the ballot for his House seat and won a third term easily.

But after a short period of working to gain Mr Trump’s favour by aggressively criticising the investigation into Russian interference in the 2016 presidential election by Special Counsel Robert Mueller, the then-president rewarded Mr DeSantis’ loyalty with an endorsement when he ran in the 2018 Florida gubernatorial primary.

After winning the GOP nomination, Mr DeSantis barely beat his Democratic opponent, former Tallahassee mayor Andrew Gillum, winning his place in the Florida Governor’s mansion by less than a percentage point.

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His ascent in Florida coincided with large levels of inward migration into Florida, a state with no income tax. At the same time, a steady drumbeat of GOP messaging which cast even the most moderate Democats as “socialist” helped push Latino voters — many of whom were immigrants from countries with actual socialist governments — to begin casting votes for Republicans.

With those winds at his back — and a newfound prominence in right-wing media thanks to his rejection of Covid vaccines and public health measures such as masks — Mr DeSantis won re-election in 2022 by slightly less than 20 points, even flipping historically Democratic areas like Miami-Dade County.

His win atop the midterm election ticket coincided with historic Democratic losses on the state level, leaving Florida Democrats in a weaker minority status in the state legislature and leaving the party without a single representative among statewide elected officials.

But when Mr DeSantis departed Washington after winning the governor’s mansion in 2018, he did so with few friends other than Mr Trump, whose support among the Florida delegation remained strong enough that the Florida governor’s much-hyped visit to the Capitol earlier this year ended with multiple Florida congresspersons walking out of a meeting with him to declare that they were endorsing the former president once again.

One of those members was Representative Byron Donalds, a second-term congressman who represents the Sunshine State’s 19th District.

Mr Donalds, who in the past has been a close ally of the Florida governor, said in a statement that he was backing the twice-impeached ex-president over his own state’s governor.

“There is only one leader at this time in our nation’s history who can seize this moment and deliver what we need — to get us back on track, provide strength and resolve, and Make America Great Again,” he said.

He had previously praised Mr DeSantis as having done a “tremendous job” during a recent appearance on right-wing commentator Megyn Kelly’s satellite radio show, but he also said Mr Trump’s prior experience gives him “muscle memory” that will provide an advantage in next year’s battle with President Biden — and in a second term.

“Donald Trump has been through these fights. He knows where these landmines are and so he can walk in and be effective,” he said.

That visit and the subsequent loss of support among his own congressional delegation was an early sign that the factors that led Mr DeSantis to newfound celebrity on the right may not be enough to overcome his awkwardness and apparent aversion to social interactions. And those same factors — his rejection of anti-Covid measures, his support for culture war bellicosity, book bans, restrictions on gender-affirming care and opposition to the teaching of Black history — could make him toxic on a national stage.

As a result, Democrats hope a White House run will show him to be little more than a delicate flower who will wither under the hot lights of a presidential campaign.

Rep Maxwell Frost (D-FL), a vocal critic of Mr DeSantis who heckled him at an event years ago, told The Independent that he is relishing the idea of a Trump-DeSantis primary fight.

He said he’d take pleasure in “arguably two of the worst people in politics going at each other” and acknowledged that the sniping between the two thus far has provided “some entertainment”. But he also noted that there’s a danger to giving either Mr DeSantis or Mr Trump a chance to get into the White House.

“The unfortunate part is that, you know, the impact is real,” he said. “It’s important and I’m gonna be one of the people out there beating the drum for people to know how horrible both of them are, but specifically DeSantis.”

Rep Debbie Wasserman Schultz (D-FL), who briefly served with Mr DeSantis in the House of Representatives, said she took no enjoyment from watching Mr Trump and Mr DeSantis bicker.

“There’s nothing pleasurable about Ron DeSantis or Donald Trump,” she told The Independent. “The hell that he’s wreaked on us in our state has been devastating to education, to health care, women’s reproductive decisions.”

Ms Wasserman Schultz said she hoped Mr DeSantis’ run would be the beginning of the end of his political career.