Ron DeSantis Takes On the Likability Issue (Sort Of)

TALLAHASSEE, Fla. – When a couple hundred major donors to Gov. Ron DeSantis’s inauguration arrived at a candlelight dinner to the sounds of a solo saxophonist the night before his swearing-in last week they found a pair of surprises waiting for them.

In a departure from the pedestrian fare found at most political banquets, DeSantis, a food-lover with Italian roots, flew in the crew from Carbone, the trendy, New York-founded restaurant chain that moved to Miami last year, to both make a point about companies relocating to Florida and to offer a treat to contributors who gave at least $25,000.

Yet what was even more of a thrill to the donors than Carbone’s signature spicy rigatoni was what happened during the dinner: DeSantis and his wife, Casey, went table to table greeting and thanking the attendees.

Such a gesture would hardly be noteworthy for most politicians. But the early rap on DeSantis from his fellow Republicans is that, for all his smarts and shrewdness, he lacks charm, and is either unwilling or unable to submit to the longstanding rituals of retail politics.

So the mere fact that he table-hopped at a dinner in his honor -- and that more than a few of his contributors were thrilled enough about the personal touch to recount it to me after the closed-press fete -- is revealing.

The governor’s glad-handing illustrates that he’s absorbed the critique about his aloofness and is making an effort at rebutting it. The delighted response about an unremarkable show of gratitude demonstrates how little of it he’s done to date; and the relish with which his glancing interactions were recalled indicates how low the expectations bar is for DeSantis and what it means to an important constituency when he clears said bar.

He could use more such moments.

With the Republican hunger for an alternative to Donald Trump intensifying, and way-too-early polling suggesting DeSantis is the beneficiary of this ravenousness, anecdotes about the governor’s aversion to schmoozing are piling up like, well, so many order tickets at Carbone during Friday dinner rush.

There was the retreat DeSantis held for his own contributors in Miami last month, during which his face time was far less than expected. In November, it was the Republican Jewish Coalition’s conference in Las Vegas, where he flew in to speak and left, spurning offers of a meet-and-greet. And at the end of 2021, in Palm Beach, there was the “fireside chat” session he did for Republican Governor’s Association donors with Charles Schwab, during which DeSantis all but delivered his stump speech and the famed investor cracked that the governor didn’t get to do both the question and answer part of the conversation.

And for all the praise he received for his inauguration eve meet-and-greet turn, the grumbles returned the next night at the black-tie ball when an array of contributors were turned away from a not especially long VIP photo line.

When one of the donors who missed out grumbled that one doesn’t become president by pulling such maneuvers he was quieted by a young aide, according to a person who heard the exchange.

“Donors are used to a lot of care and feeding,” deadpanned Francis Rooney, a Florida man who knows of what he speaks. Rooney was himself a major Republican contributor — George W. Bush rewarded him by making him Ambassador to the Vatican — before winning a congressional seat anchored around Naples.

Rooney thinks the party’s financiers are ready to move on from Trump — “I’ve talked to a lot of CEOs down here that were all in for Trump and they’ve all dropped him now — and he is fond of DeSantis. The two Republicans go back to DeSantis’s first congressional race, in 2012, when Rooney hosted a fundraiser in Southwest Florida for him.

Yet Rooney was candid about DeSantis’s persona.

“Ron is a little reserved and dry compared to George W. Bush and Bill Clinton,” Rooney told me. “He is what he is. So what he needs to do is organize his campaign to minimize that characteristic.”

The griping, for now, is coming mostly from Republican donors, some of whom crave contact from politicians nearly as much as lower marginal rates and reliable Gulfstreams. Yet the complaints about his interpersonalskills are symptomatic of a deeper challenge for the governor, of which he and his small inner circle have told people they’re conscious: his capacity for forging connections with people

In fairness to DeSantis, he’s not even a candidate yet — and likely won’t be an official one until after Florida’s legislative session wraps up this spring. He’ll have ample time to make a better second impression with some Republicans and a fine first one with those who’ve yet to meet him. It also helps that many Republican voters, at least the ones eager to move past Trump, want to like him because they sense a winner.

Moreover, some of his restraint is strategic. Why enlarge the size of the bullseye on your back this early, when Trump is already fuming about you, by accepting an invitation to a see-and-be-seen event like the annual Army-Navy football game? (DeSantis declined a chance to go to the pageantry-laden contest last year, perhaps averting a series of lightning bolts hurled from Mar-a-Lago).

DeSantis’s deficiencies, however, can’t be easily dismissed. They get at the heart of a much larger question, something more consequential than even donor vanity, that will shape his prospects in 2024: how much does retail politics still matter in presidential campaigns?

More to the point, was Trump an exception, a celebrity playing by a different set of rules, or a turning point in presidential primaries? In 2016, he ignored the purported expectations of early nominating states, blowing in and out with large rallies, made little attempt to court Republican lawmakers and, no, wasn’t calling donors and remembering their kids’ names.

DeSantis has thrived in Florida, and made a national name for himself, with his piercing attacks on the left and gift for finding the erogenous zones of the new right. And he’s done it mostly thanks to his ubiquity on Fox News and with a series of news conferences or public events that went viral.

Which is to say he’s gotten to this point by harnessing his talents for wholesale politics, without needing much retail skill. And if we’re being honest, it’s those same skills — and not one-on-one politics — that vaulted the unexpected breakout star of the last presidential primary, Pete Buttigieg, into contention. He initiallycaught on in Iowa and New Hampshire because most voters there had first seen him on a screen, not in person.

He also didn’t become the nominee. Buttigieg dropped out after South Carolina, a state that revived Joe Biden’s candidacy in part because he had, yes, deep relationships from years of visits and important backing from validators like Rep. Jim Clyburn (D-SC), who endorsed Biden after he lost the first three states.

Now DeSantis will test if the state-by-state contests have wholly become soundstages for a national race fought on televisions, laptops and phones — and how much relationships, with donors, voters and other lawmakers still count.

The fact that a just-reelected governor is already so well known, and liked, by Republicans beyond Florida is a testament to how much politics has already shifted.

“He’s really the governor of red-state America,” is how Justin Sayfie, a longtime Florida Republican politico who once worked for then-Gov Jeb Bush, put it.

In fact, it’s hard to recall a governor since Jeb Bush’s older brother who was poised to enter a presidential primary with higher expectations.

Then, like now, Republicans had suffered a disappointing midterm under a Democratic president and were eager for new faces who could unite their quarrelsome factions, preferably ones from outside Washington who had just put together smashing re-election victories with diverse coalitions.

Yet the differences between George W. Bush in 1999 and Ron DeSantis in 2023 are just as instructive as the similarities.

When the National Governor’s Association convened in February, just a few months after Bush’s re-election and even before he announced his presidential bid, a dozen other GOP governors preemptively backed the former president’s son.

I asked one plugged-in Republican governor if any from today’s ranks would back DeSantis before he announces or even on the first day of his candidacy and the, quick, answer back was: “I don’t think so.”

Consider the difference vis a vis their relationships with a pair of moderate Massachusetts GOP governors, a generation apart. Then-Gov. Paul Cellucci attended Bush’s inauguration in 1999, and later was tapped as Ambassador to Canada yet when DeSantis dispatched a plane full of migrants to Martha’s Vineyard last year he didn’t even give former Gov. Charlie Baker a heads up. Nor did any other current governors show up for DeSantis’ inauguration.

If not as needy as donors, high-level politicians expect to be treated with goodwill and respect by one another. And DeSantis has done little to win over other Republican governors, to leaven the inevitable jealousy that comes from all those Fox News invitations.

In fact, he’s shown next to no interest in building relationships with governors, one of whom described the Floridian’s approach to events as presidential — he comes in through the kitchen, speaks and leaves. For a glimpse at how GOP governors view DeSantis, take in the interview my colleague Ryan Lizza did last month with Chris Sununu, the governor of a consequential state last I checked, who said “there’s a lot of hype and headlines” with DeSantis but “you got to earn it at the end of the day.”

Another governor told me that when somebody asked how best to reach DeSantis, this governor Googled the contact information for the Florida governor and shared what he found online.

It’s a far cry from what Bush enjoyed, when a phalanx of governors offered their endorsements, strategists, donor networks and, often, control of their state parties.

“Anybody else looking at it said, man, that’s a lot to go up against,” John Engler, the former Michigan governor and early Bush backer, recalled of the show of force he helped engineer. With Trump still lingering, and retaining considerable grassroots support, Engler said it was no less vital for DeSantis to win support from other governors today than it was for Bush.

“That’s considered old school these days but I do think those relationships matter and I think they’re especially important following the Trump era, when you’re trying to unite this party and the country,” he told me.

Like Clyburn with Biden, you want allies who will stand with you when the going gets tough.

DeSantis, though, has other relationships that may pay off — and that reflect how the GOP has shifted since Bush’s rise.

Taking in the inauguration and lively hotel lobby and restaurant scene in Tallahassee — a state capital with only so many places to run into people — I was struck by DeSantis’s hybrid coalition-in-waiting.

Pillars of the Republican Establishment were there.

There was Jeb Bush, who was greeted with applause when he walked out onto the stage set up in front of the old state capitol, and the longtime father-son donor duo of Fred and Jay Zeidman, in from Houston at in the front row.

Between the venerable Governor’s Club and the hot new spot in town, Il Lusso, were a battalion of Florida players, like former state House Majority Leader Adam Hasner, Senator George LeMieux, and lobbyist kingpin Brian Ballard, who once represented a hotel magnate named Trump’s Florida interests. Also in attendance from Trumpworld was Wilbur Ross, the Palm Beach billionaire turned commerce secretary.

And over at the Tallahassee airport — where the charter terminal is indeed called Million Air — there were black Suburbans queued up on the tarmac and on the curb outside to transport the contributors flying in from out of state and Boca Raton, Naples and Palm Beach.

Yet just as significant was the turnout from the new vanguard of Trump-era Republicans, people like venture capitalists David Sacks and David Blumberg as well as conservative talk show hosts and Florida emigres, Dave Rubin and Lisa Marie Boothe.

If DeSantis is to overcome Trump, unify the party and claim the presidency, it will be because he connected with such a broad coalition and the constituencies they represent.

His speech, also, reflected the two layers of his appeal.

On the surface, it was pure DeSantis, combative, partisan and boosterish without a hint of the let-us-now-come-together calls for unity that are usually the stuff of inaugural addresses. He’s selling the Florida Story — “number one in these United States in net in-migration,” he bragged — but he doesn’t exactly project sunniness when selling the Sunshine State. And while we’re on alliteration, some of the rhetorical touches were less than soaring, more like an AI version of what Pat Buchanan and William Safire produced for Spiro Agnew.

Yet there was a subtler theme to the address.

DeSantis offered implied, for now, contrasts with the Trump administration. The governor lashed the federal government for Covid restrictions which “eroded freedom and stunted commerce” while decrying Washington’s “spending binge.” He hailed a litany of great Americans, beginning with George Washington, that notably included one modern Republican president (Reagan) but did not include a more recent one (Trump).

Perhaps most significant was another area of contrast with Trump, one that may appeal to voters who aren’t as moved with jeremiads against wokeism: competence. “Florida shows that results matter,” said DeSantis, recalling how the state responded to hurricanes. “We lead not by mere words, but by deeds.”

Gee, who’s fond of words?

Not that many Republicans in the audience, or watching on television, needed a reminder about the ways that Trump and DeSantis differ. Every conversation I had with attendees during my trip eventually, and usually quite quickly, came to Trump. Few were harshly critical of the former president, they just don’t think he can win a general election and are confident DeSantis will if nominated.

Most memorable — and a reminder that all is relative when it comes to DeSantis’s shortcomings — was Jody Fameree.

I came across Fameree, a manufacturing executive who came up from Tampa for the swearing-in, as we both left the old capitol grounds. Less than 30 seconds into our chat, he invoked his preference of DeSantis over “the alternative.”

Why?

“I like his personality,” said Fameree, “he’s not as abrasive.”