DeSantis stumbles while seeking to stick Trump with loser label

Florida Gov. Ron DeSantis (R) is running into early problems as he tries to cast former President Donald Trump as a loser while opening his presidential campaign.

DeSantis and his allies have focused on Trump’s losing record in recent elections to set up the Florida governor as a worthy alternative to the ex-president with GOP primary voters. DeSantis has specifically told GOP voters to “reject the culture of losing.”

“Governing is not about entertaining. Governing is not about building a brand or talking on social media and virtue signaling. It’s ultimately about winning and producing results,” DeSantis told voters during a recent stop in Iowa in a swipe at Trump without naming the former president.

DeSantis does have a case to make: The GOP lost the House while Trump was president in 2018, Trump lost his reelection bid in 2020 and the GOP failed to win back the Senate in 2022 — while retaking the House with a smaller majority than expected.

A lot of the blame for that was placed at the feet of Trump, who backed various candidates for office throughout those campaigns who were defeated. 

Yet casting Trump as a loser is complicated for DeSantis. 

For one thing, two candidates backed by DeSantis just this week lost high-profile elections — one of them to a Trump-backed rival in the Kentucky gubernatorial primary. 

Another DeSantis-endorsed candidate, Daniel Davis, lost the Jacksonville mayoral race Tuesday to Democrat Donna Deegan. While the governor threw his support behind Davis, he never campaigned with him, nor did he use his political influence to try to muscle Davis across the finish line.

Still, Davis’s loss came at a price for DeSantis, said Ford O’Connell, a Republican strategist.

“The lesson here is that he needed to campaign for him. He should have done that,” O’Connell said. “And when you’re gallivanting across the country, it doesn’t look good back home. He took an arrow out of his winner-argument quiver.”

The dual losses also emboldened Trump’s team to take aim at DeSantis’s record. In an email blasted out to reporters Wednesday, the former president’s campaign mocked what it called DeSantis’s “culture of losing.”

Casting Trump as a loser also forces DeSantis to wade into the 2020 election. Trump lost that election, but many GOP voters refuse to accept it, and DeSantis himself has danced around the issue and avoided saying whether he believes the result was rigged or fraudulent.

National polls have consistently shown Trump with a healthy lead among GOP primary voters, followed in most cases by DeSantis. As the Republican field takes shape and candidates look for ways to shake Trump’s grip on the party, strategists believe that perhaps the clearest argument that will resonate with voters is to point to the party’s lack of success during recent election cycles.

“[DeSantis] has to remind people that Donald Trump is a three-time loser,” said one former Trump campaign adviser who now supports the Florida governor in a primary. “That Donald Trump has left the Republican Party in an extremely weak position. That Trump is almost dead on arrival come the general election.”

DeSantis reportedly sought to make that case to donors during a conference call Thursday organized by Never Back Down, a super PAC supporting him as a presidential candidate.

“You have basically three people at this point that are credible in this whole thing: Biden, Trump and me,” DeSantis said on the call, according to The New York Times. “And I think of those three, two have a chance to get elected president — Biden and me.”

While Trump has dominated national GOP primary polls, leading DeSantis by more than 20 points in some recent surveys, the Florida governor has fared better in state-level polling. Two polls released Friday by Public Opinion Strategies showed DeSantis narrowly leading President Biden in the key swing states of Arizona and Georgia, while the president edged out Trump and former Vice President Mike Pence in hypothetical head-to-head matchups.

DeSantis’s rise as perhaps the most formidable alternative to Trump has also been shaped by his team’s efforts to frame the governor as a winner, pointing to his landslide reelection victory last November and his laundry list of conservative reforms enacted under his leadership.

“Governor DeSantis has never lost an election, ever,” Erin Perrine, the communications director for Never Back Down, said in a statement. “He won a massive electoral landslide during his 2022 re-election in Florida because he led with strong policy positions, and Floridians have supported those overwhelmingly.” 

“As a result, Governor DeSantis was able to continue locking in legislative wins that have improved the lives of Floridians by signing into law a Parental Bill of Rights, getting the smut out of schools, and standing up against woke corporations.”

O’Connell said the challenge for DeSantis is getting that message across to voters outside of his home state, who might not be as familiar with his record as Floridians are.

“The issue DeSantis has is understanding that he’s not just in Florida anymore,” he said. “You go to other states, and they don’t know about his victories unless he tells them. And he’s gotta find a way to communicate that quickly on the stump and not have 40-minute friggin speeches.” 

As DeSantis prepares to formally enter the primary field next week, Trump and his team are expected to ramp up what has already been a steady stream of attacks against the Florida governor to shatter the notion that DeSantis is more electable in a general election.

The Trump campaign and its allies even used Sen. Tim Scott’s (R-S.C.) entry into the 2024 race as a chance to argue DeSantis has failed to clear the rest of the field of rivals.

“Tim Scott’s entrance, and aggressive media purchase, doesn’t only kneecap DeSantis, but Scott sees the same thing as [Virginia Gov. Glenn] Youngkin, [New Hampshire Gov. Chris] Sununu, [North Dakota Gov. Doug] Burgum, [Former New Jersey Gov. Chris] Christie, and others: the path to 2nd place is wide open,” Taylor Budowich, head of the Trump-aligned Make America Great Again Inc., said in a statement. “They smell Ron DeSantis’s blood in the water and no longer see him as an obstacle.”