Trump’s Case of DeSantisitis

DeSantis and Trump
Florida Governor Ron DeSantis and former President Trump. Photo: Mark Wilson/Getty Images
Tara Palmeri
June 23, 2022

It’s winter in Bedminster: Donald Trump’s golden endorsement was put to the test this primary season with a number of high profile races that came back with mixed results. With the election cycle halfway over, the line to kiss the ring has substantially shortened. And those who received Trump’s blessing in swing states have already started to distance themselves from him, like Dr. Mehmet Oz in Pennsylvania, who notably dropped Trump from his branding materials, or Herschel Walker in Georgia, who dissed Trump after winning the primary. Just months ago, ambitious Republicans were making pilgrimages to Mar-a-Lago to beg for his endorsements, hiring aides with connections to him and asking old rich guys, like Bob Kraft, to call in favors. Now, the sojourns to Bedminster are becoming more rare. 

Trump is not only lonely, he’s in a slump. He’s absorbing hits almost daily via the January 6 committee, as his own closest aides have been questioning his judgment and sanity on the record. Even the former president’s greatest champions will quietly admit that it’s not a great look, especially since the party has done little to defend him. His own mode of defense, Truth Social, hasn’t taken off, either. At the same time, there has been a steady drumbeat of stories about how Ron DeSantis has become the new standard bearer: a fresher, less impulsive version of Trump, and with less insurrectionist baggage. DeSantis managed a net-neutral feature treatment in The New Yorker, and scored an early presidential endorsement from Trump’s hometown paper, The New York Post. (Also, I highly suggest reading my Puck partner Tina Nguyen’s excellent piece on the complex, airtight political relationship between DeSantis and his wife, Casey.)

Perhaps more notably, DeSantis has also earned a slew of stories about how he has successfully tapped into Trump’s fundraising network, allowing DeSantis-curious and/or Trump-fatigued donors to put their cash toward his $124 million war chest under the cloud cover of contributing to his competitive 2022 gubernatorial re-election. Polls also show DeSantis creeping up on Trump. A Doug Kaplan poll from February showing Trump beating DeSantis by 15 points in a Florida Republican primary has been soothing his inner circle, but the political mood has undeniably shifted since then.

Just as Trump’s position as the party’s kingmaker is now being questioned, the number of Republicans signaling that they are willing to run against him in a primary grows by the week. And Trump is aware, according to my sources in his orbit, that this election won’t be like 2016, when he was the only candidate talking about that big beautiful wall. The people who could run against him now are weaned off of his preternatural ability to detect the fears of the Hannity base. These next-gen candidates may be less magnetic, but they’re also less erratic, which soothes anxious donors. And Trump is taking note of how they’re wooing his donors, because he cares about money. (“President Donald Trump maintains an unprecedented endorsement record that is propelling an entirely new wave of America First leaders, making it clear that voter-demand for the leadership of President Trump continues to grow for 2022 and beyond,” said Trump’s spokesperson, Taylor Budowich.)

All of this has made Trump angry, according to those close to him, and, frankly, nervous. He’s been asking aides why there are so many stories about DeSantis, and the recent buzz around the governor has emerged as a major factor pushing Trump towards making an early announcement about his candidacy. Months ago, sources close to Trump told me that he was motivated by Joe Biden’s vulnerability, on top of his own impulsive desire to announce his candidacy and dominate the news cycle. Now I’m hearing that an announcement is more a move of necessity in order to freeze the field and preserve his political future. “It’s to steal the march on Ron,” said a source close to the former president. “I think he thinks it will staunch the bleeding of supporters moving to Ron.”

Trump’s team is already taking notes on MAGA influencers, particularly in Florida, who have been touting DeSantis on their handles and in media appearances. “They are watching closely,” said another advisor to Trump. Indeed, aides expect some sort of loyalty test to emerge after Trump announces, which they are all preparing for. When speaking to his closest aides, it’s not if he’s going to announce but when, as they try to sort out all of the back office issues in anticipation of his announcement. “It’ll become, are you with me or Ron?” said the first Trump advisor. “And he thinks that he’ll win those individual contests.” 

What can DeSantis do about it? Surely, he can’t announce that he, too, is running for president before he is sworn in for a second term as governor of Florida in January. And he’s also not taking the threat of former Republican Charlie Crist lying down. (Loyal readers will recall how I reported that Tony Fabrizio has circulated polling suggesting that the race is neck and neck.) But DeSantis does have that $124 million dollars in the bank, much of it from the G.O.P. donor class that is enchanted by his youth and discipline, with more to spend.

These donors do not want to dig deeply into their pocketbooks for a presidential election before a midterm, and many are quietly dreading any type of early announcement from Trump. Many are also privately fearing that an early announcement could complicate what looks like a comfortable Republican victory in the midterms, at least in the House, by turning the elections into a proxy referendum on another four years of Trump. On the campaign trail, candidates who were just endorsed by Trump will be asked whether they support him for president. At the same time, many of those candidates will likely suffer enthusiasm gaps come late September and early October and will need Trump to come out and campaign for them. There’s no turning back, unless rescinding endorsements becomes the new norm in Republican politics. So there will be an overwhelming chorus of Republicans saying that Trump is their guy, potentially making him the inevitable, ascendant candidate for president.

Many close to Trump, however, are hoping that his nerves can still be placated when it comes to DeSantis. Some point out that governors have a way of being favored early on in election cycles, like Scott Walker and Chris Christie in 2016, because of their ability to enact policies in their states that they can use as models, plus having the power of their own press corp to make news throughout the country. These governors also happen to be untested on a national stage, and face steep learning curves. There’s also the possibility that DeSantis doesn’t run. As a congressman, he strongly considered primarying a then-vulnerable Marco Rubio for his Senate seat in 2016, but ultimately backed out, lining himself up for the governor’s mansion instead. He may decide it’s not worth it to challenge Trump and have his pristine image sullied with a moniker he can’t shake. 

At the same time, these placations might not be enough for Trump to hold his fire. Biden was a late entry into the Democratic primary, and he managed to win. Luckily for DeSantis, I’ve heard that Trump has yet to settle on a nickname for him. 

The Talk of This Town…

What Gerontocracy?: I’m hearing that both Steny Hoyer, the 83-year-old Democratic majority leader, and Jim Clyburn, the party’s 81-year-old majority whip, have made it known to their colleagues that they will not be retiring or stepping down from their leadership positions if Speaker Nancy Pelosi, 82, leaves Congress after the midterms, as many expect, should the Democrats lose the House. Indeed, this will almost certainly set off a generational conflict between the old guard and a younger cohort who are quietly, but firmly, positioning themselves to run for leadership posts. As I reported a few weeks ago, New York’s Hakeem Jeffries is already sending out Junior’s cheesecakes to House members as part of his low-key campaign to curry favor.

The inevitable conflict is already creating “awkward chatter,” as one Democratic congressman put it, among members about choosing between the ascendant and relatively youthful 51-year-old Jeffries, who would be the first Black caucus leader, and the beloved and well-respected Hoyer, who many believe should not end his career with a loss. Even though an octogenarian white guy doesn’t represent the makeup of the party, he and Clyburn have been known to be supreme fundraisers who are generous with their cash to vulnerable members. They’re also willing to go to districts and campaign for their colleagues. Jeffries, while a prolific fundraiser, doesn’t have this history of bailing out members. 

There’s always the possibility that Clyburn and Hoyer make a pact to support each other in their leadership races, with Clyburn securing the support of the Congressional Black Caucus over Jeffries. Some in the House are already imagining the fractious, high school-style contest that would force friends and colleagues to take sides and create a schism in a party that needs to unify its various flanks. “The easiest [resolution] would be that they all ride off into the sunset together,” said one member, referring to Hoyer and Clyburn. “I’m increasingly concerned that won’t happen if [Pelosi] retires early on in the next term and then the others don’t, and then it becomes a real fight in the party.” 

In Defense of Klain: A long-time friend and defender of Ron Klain, and a veteran senior White House official, reached out to me this week to take issue with whatever blame it appeared I was casting on the chief of staff for Biden’s performance in a previous piece. To state the obvious, I don’t have a horse in this race: I’m simply reporting the fact that many in the party are frustrated with Biden’s administration and that Klain, as the point person, inevitably bears the brunt of the criticism. That’s hardly a secret in Washington. Still, I’m always happy to listen and I wanted to report on our conversation.

This long-time Klain ally made a couple of good points. In particular, this person, a former White House veteran, reminded me that Biden is exceptionally stubborn. And the caricaturesque perception that Prime Minister Klain is managing an enfeebled Biden misses the point. Klain entered Biden’s orbit as a young staffer and he doesn’t have the sort of relationship with the president where he can easily guide his decision making. While chiefs of staff have an exceptional amount of power as gatekeepers, they are not bulldozers. This person conceded that the baby formula issue, because it started as a communication issue with Biden, could be something to blame Klain for, but the way Biden has handled Congress and his agenda is not Klain’s fault. (The White House forcefully disputed my characterization.)

The Jill Factor: All eyes are on Jill Biden as her husband ponders a second run. As I reported last week, the official line in Bidenworld is that the president is running for re-election, and merely pondering an announcement strategy. But many are wondering if that position is immovable. I previously noted that Biden’s family is foremost on his mind, and if anyone has a say on whether Biden should run again it’s the first lady. Jill was doing as many as four events per day during the 2020 primary and general election cycle, and whether her heart is in it will be a major consideration. 

As for Biden’s kids and grandchildren, I’ve heard they’ve been lamenting that Pops doesn’t deserve this, after he pulled the country out of the devastation caused by Trump. They believe the criticism that he has received over the state of the country is unfair considering that he’s given his whole life to service and has reclaimed the dignity of America’s most important institution. As for Biden, his natural inclination is to run again. It’s all he’s ever done.