Jeff Roe’s Declaration & the DeSantis Inner Circle

In many ways, Ron DeSantis’s inner circle is really only composed of himself and his wife, Casey.
In many ways, Ron DeSantis’s inner circle is really only composed of himself and his wife, Casey. Photo: Michael Reaves/Getty Images

We’re about six months away from the first G.O.P. primary debate and the jockeying and positioning within the 2024 field feels a little stunted. The counting of the first ballots is less than one year away. So in what is fast becoming a weekly tradition around here, I reached out to my partner Peter Hamby to discuss the different considerations for each candidate about when to enter the race, their emerging strategic lanes, and how the much-anticipated TrumpDeSantis slugfest factors into it all. Plus, how DeSantis’s former staffers could be a boon to Trump and how Biden’s student loan relief struggles may affect his reelect. 

Tara: This already feels like the longest primary ever, especially since it started after the midterms with Trump’s announcement, and yet it has barely even begun! As I’ve noted recently, I’m also hearing that Glenn Youngkin, Chris Sununu, Chris Christie, and Rick Scott are all exploring this idea of a late entry in the 2024 Republican primary, perhaps in summer or even early fall, ostensibly after Trump and DeSantis have had their way with each other. Do you think that’s a viable option?

Peter: My short answer is no, not really. I was struck by a recent New York Times analysis by Nate Cohn showing that there’s actually a pretty decent historical correlation between a candidate’s early support in the polls and the eventual winner of the nomination. Trump in 2016 was the big exception in recent memory, but Cohn’s data is correct. If you’re polling in high double digits at this point in the campaign, you tend to have the best shot. DeSantis (around 30 percent support in most polls) and Trump (usually polling around 40 percent) are the only two candidates in that discussion. If you’re polling in low single digits at this point in the race—approaching the conclusion of the first quarter of the year—modern history shows you’re a non-starter. 

A lot of people misremember Barack Obama as a long-shot on the Democratic side in 2008. But Obama had already been maneuvering the invisible primary before his early campaign announcement in 2007—touring the country, lining up endorsements and getting financial commitments from major donors. He also had a built-in aura of fame with grassroots progressives dating back to his 2004 convention speech, his anti-war bona fides and his celebrity-like book tour for The Audacity of Hope. DeSantis has a similar kind of organic support without formally having a campaign. By the end of the first quarter of 2007, Obama had raised about as much as Hillary Clinton and was polling above 20 percent among Democratic primary voters, just 10 points behind Clinton. It was really only a two-person race from that point on. There are also plenty of examples on the Dem side of late-entry candidates who came in with hype or media buzz but proved to be duds: Wesley Clark, Mike Bloomberg, and Deval Patrick come to mind. On the G.O.P. side, flameouts like Fred Thompson in 2008 and Rick Perry in 2012 demonstrated how cringey it was to show up to the bar right before last call.

Tara: Fair enough. I get the feeling that these late entrants are just trying to stay out of Trump’s way and are curious to see how he fares this time around, with lower energy, less visibility and questionable electability, which is the great unknown.

Peter: The 2024 dynamics on the G.O.P. side are a little weird this year, obviously. Trump is a wounded stray dog—weakened, but still ferocious. DeSantis hasn’t even declared yet, but his consultants are already building a campaign and a super PAC, as I reported a few weeks ago. His biggest flex so far, in my mind, was that “Florida blueprint” donor event he held in Trump’s backyard of Palm Beach. A bunch of movement conservatives showed up, including Senators Ron Johnson, Tom Cotton, and Mike Lee, as well as former die-hard Trumpers like Ann Coulter, Congressman Chip Roy and Trump’s former chief of staff Mick Mulvaney. The very fact that such conservative validators were willing to cross the former president to show their faces at a DeSantis event demonstrates that the Florida governor has a kind of power broker support inside the G.O.P. that none of the other possible contenders do. 

In the primary, Trump will have limitless small donor support, a built-in base and universal name ID. Compared to the names you mentioned—Youngkin, Christie, Sununu, or even Mike Pence—DeSantis is currently the only one who can rival him in any of those categories. And Rick Scott has about as much personal charisma as a piece of wet cardboard. So, I suspect Youngkin, Christie and the rest are waiting to see if DeSantis fizzles—maybe in that first G.O.P. debate in August—and then they can make a move.

Tara: The thinking among both Rick Scott and Youngkin’s teams is that they are both personally wealthy individuals, and can buy infrastructure if they jump into the primary late when Ron and Don are mortally wounded, and maybe even swoop in to take their infrastructure and staffers looking to cut loose. Summer is a long way away, and Scott has a late Senate primary in Florida so that gives him some optionality. I doubt he likes reporting to Mitch McConnell. As for Youngkin, he can only serve one term.

Peter: It certainly helps to be able to self-fund, or to have some Republican sugar daddy who can fund your efforts, like Sheldon Adelson did with Newt Gingrich in 2012. But without much support from party brahmins or any base of support in the early states, it’s hard to see how any of these guys could step in and suddenly come from several laps behind to overtake Trump. This is also why I give Nikki Haley some credit for stepping in early. She’s an afterthought right now, but at least she’ll have the bones of a campaign in place to get hot at the right time if DeSantis doesn’t actually run, or live up to the hype. 

Tara: I think you will definitely see Tim Scott, Mike Pompeo and Mike Pence jump into the race, too, likely before June. After all, what else do they have to do? Tim Scott has said this is his last term in the Senate regardless of what he decides to do. Some of these guys may also be positioning themselves for vice president—Scott wouldn’t name a single policy difference with Trump’s MAGA agenda when asked about it last week. Is it just a profile-elevating exercise? Of course, Trump will welcome all of them in. It only lowers his threshold in the primary. 

Peter, You’re a Virginia native who knows the political terrain really well. I know you’ve been home recently to see your parents. What do you think of Youngkin’s ability nationally to straddle the pro-Trumpers, never Trumpers and independents? Is that a model that can win a G.O.P. primary or just a general election?  

Peter: Thank you for shouting out my parents in Richmond, who are obviously unbiased Puck superfans and some of our earliest paid subscribers. When you land at Richmond International Airport these days, one of the first things you see on the way to baggage claim is a sleek “Welcome to Virginia” video from Youngkin, showing him at one point zooming around the city’s NASCAR track. It’s basically an economic development video, because that’s what Virginia governors, Democrat and Republican, have been selling for decades. Virginia is for lovers! But it’s also good for business, public schools, decent taxes—and ambitious governors. 

I mention this because it often feels like Youngkin is sometimes in friendly-dad business guy mode, and sometimes in right-wing ideologue mode. And he can’t decide which suit fits him best. In the Trump era, that just spells trouble in a Republican primary. DeSantis, so far, seems totally happy governing like a red-blooded culture warrior. He went to war with Disney, one of Florida’s largest employers, over the company’s perceived “wokeness.” I just can’t see Youngkin going after Capital One or Altria in the same way.

Youngkin is a Christian churchgoer and he’s certainly governed like a right-winger—banning discussions of critical race theory in public schools, rolling back protections for trans students, and undoing state efforts to fight climate change. But, to me at least, Youngkin has always given off the whiff of a Mitt Romney country clubber, not a red-hat type who posts vaccine theories on Facebook. After all, like Romney, he is a former private equity C.E.O., a grinfucker who has elevated grinfucking to an art form.

I felt that way when he was running in 2021, too. Remember, Youngkin didn’t win a Trumpy statewide Republican primary to get the nomination. He won a modified, ranked-choice vote of about 30,000 activists and party insiders. His campaign wasn’t totally an act, but there were times when it seemed like he was just cosplaying a MAGA dude. He presented as a normie golf dad to win over Biden voters, and then went on Fox News to talk to the Republican base about C.R.T. Sure, the Harvard M.B.A. and former Carlyle Group C.E.O. might be a compelling general election candidate. But does Youngkin have the guts—or the total lack of shame—to out-angry Trump or DeSantis in a primary dogpile? Call me skeptical. 

Youngkin’s consultant in the 2021 race, Jeff Roe, apparently agrees. Roe went on Fox News last week and declared flatly, “The reality is, this is a two-person race between Donald Trump and Ron DeSantis… There’s simply no room for a third or fourth, or even fifth person in this race.” Roe later backtracked, but given Roe’s close association with Youngkin, his remark suggested to me that either Youngkin won’t run, or that Roe is inching toward a job with either DeSantis or Trump in 2024. 

On that note, Tara, how do you see the leadership for both of those campaigns shaping up? Who is going to manage DeSantis and Trump, and what might their hires say about their competing leadership styles?

Tara: Well, I think both men have a similar take on consultants—they should execute the vision of a client, not the other way around. Trump’s team right now is small, loosely organized and likely to have a lot of shakeups. I will say that I’m impressed by how Susie Wiles has been able to stay atop the organization for two years, mainly by not being power hungry, deferring to Trump, and ditching a conventional hierarchy by flattening the top of the org chart with Chris LaCivita and welcoming others in like Jason Miller. At the end of the day, it’s the Trump show, so what’s the point of even trying to change that? 

As for DeSantis, his inner circle is really only composed of himself and his wife, Casey. I hear that Generra Peck, who led his very successful reelect in 2022, is likely to be his campaign manager, and like you reported, Phil Cox will run his super PAC. There’s Adam Laxalt and Brian Ballard hanging around the hoop, as well, but DeSantis has always had very little use for consultants and staffers. 

Trump tends to churn and burn staff, too, but he also reaches out to everyone for advice, even polling members at Mar-a-Lago. That is not DeSantis’ style. The answers lie with himself and Casey. In fact, so many of his former staffers felt disrespected by him over the years that they started a support group, as I reported for Politico in 2021. No one around him has really been there for very long. He’s had three chiefs of staff during his one term as governor. For Trump, having Wiles, one of the many DeSantis ex-staffers who left feeling burned, at the top of his team could actually be a huge asset. She’s Florida based and has a real institutional knowledge of his rival. There are other spurned DeSantis staffers who are now with Trump, but not the other way around. It makes for an interesting dynamic. 

Meanwhile, looking at Democratic politics, it seems like Biden’s student loan relief plan is doomed to failure with this Supreme Court. At least that’s everyone’s sense after oral arguments were made for and against the plan late last month, which is being challenged by Republican states as definitional executive branch overreach. If Biden’s executive action gets killed, how badly does it damage his presidency?

Peter: It’s definitely a blow, especially for a president who views himself as the most consequential president on domestic economic policy since L.B.J. Biden himself didn’t sound very optimistic after the conservative justices voiced real skepticism about the student loan plan, which would erase up to $20,000 in debt for more than 16 million borrowers. “I’m confident we’re on the right side of the law,” Biden said last week. “I’m not confident about the outcome of the decision yet.” The White House isn’t talking about backup plans yet, and they can cling to a sliver of optimism. The justices aren’t just debating the merits of the student loan plan. They’re also debating whether the G.O.P. states even have legal standing to challenge the student loan plan at all. The court could still conclude that they don’t, throwing out the case. 

Back in early 2012, there was similar anxiety inside the Obama White House, when a lot of people in Washington thought the Court would gut Obamacare. Instead, the Affordable Care Act was surprisingly upheld, thanks to Chief Justice John Roberts. But even if Biden’s plan survives this round, it’s sure to face more legal challenges. As unsettling as that is for borrowers who were counting on loan relief, it does set up a helpful political dynamic for Biden heading into his possible re-election campaign. Whether or not his plan lives or dies, Biden can continue to present himself as a warrior for working and middle-class Americans against Republicans who don’t want to extend a helping hand. 

The student loan action also gave Biden some desperately needed street cred among Gen Z and Millennials, who were pretty unenthused about his presidency before he announced the plan in 2022. A Wall Street Journal poll from just before the midterm elections showed as much: While only 48 percent of the American public favored Biden’s loan relief plan, almost 60 percent of voters aged 18-34 backed the plan. Exit polls from the November midterms also showed that an overwhelming majority of Democrats backed the plan, and support from younger voters helped blunt G.O.P. gains at the polls. 

So even if SCOTUS kills his student loan agenda, Biden could at least run for re-election boasting that he tried to fight for borrowers—and that he will keep trying. Either way, politically, I do think he has established some trust with younger voters that he didn’t quite have before his executive action last year.