A few months back, a G.O.P. operative was telling me about an old employee of his who had sought a job with Ron DeSantis, the Florida governor on a meteoric rise through the MAGA stratosphere, with all vectors pointed at a White House run in either ‘24 or ‘28 depending on the smoke signals emanating from Mar-a-Lago. The employee had already been through multiple rounds of interviews, and passed background checks. Having been deemed worthy of a meeting with the principal, he was called in for one last evaluation. To his surprise, this final interview was not with Ron DeSantis. It was with his wife, Casey.
When I mentioned that anecdote to a G.O.P. consultant, he remarked that he had heard similar stories about the “DeSantii” interview process—not just for potential employees, but for vendors and contractors, too. Sometimes, both Ron and Casey would run the interview. Sometimes, it was just Ron. If he wasn’t available, Casey was “an acceptable substitute,” this person told me. Every single time, he added, the couple would request piles of advance documentation that could impress a job candidate or scare them off entirely, but at the very least convey the magnitude of the position in question. Every dollar that the job candidate proposed in their budget needed to be accounted for in that interview, and every motive needed to be uncovered.
This consultant hypothesized that the couple are strongly aware they could be targets for graft, an endemic problem in the post-Trump Republican ecosphere. Their scrutiny and diligence, reflected in a recent New Yorker profile by Dexter Filkins, are also reflective of their own ambition and very un-Trump-like discipline, itself a potent combination for future electoral success. “It’s very smart on the one hand,” this person said, referring to the couple’s tightly controlled inner circle. “It’s also not very smart, on the other hand. It requires a surveillance state that requires a lot of resources and energy to keep up.”
Of course, a certain degree of paranoia is to be expected when you’re quietly downplaying what looks like a presidential campaign-in-waiting. Ron DeSantis, 43 years old and already a rising star inside the G.O.P., is frequently discussed as a potential threat to Donald Trump’s power. And it just so happened that the vindictive and gossipy former president is his new neighbor. Last year, Trump uprooted himself from New York City, became a full-time Florida resident, moved into Mar-a-Lago, and invited all of the DeSantises’ friends, enemies, and donors to hang out at his club and watch movies at his house. When DeSantis failed to immediately acknowledge that he would support Trump if he ran for president in 2024, it was viewed as a direct challenge, with Trump complaining to people around him that Ron had not bent the knee. Notably, Trump blabbed about DeSantis to Filkins on the record, while the DeSantis office declined to comment. (On Wednesday, the cold war entered a new and petty stage: Politico reported that DeSantis isn’t seeking Trump’s endorsement for his gubernatorial campaign, even as a liaison for Trump made it known that he would happily grant one, if only DeSantis would humble himself to ask.)
The intense speculation surrounding the DeSantii, as a couple, usually highlight Ron: ambitious, intelligent, a tactical Goldwater-esque culture warrior whose studious reserve and stiff demeanor belie an appreciation for political theater. Casey DeSantis, meanwhile, initially presents as the model Republican First Lady, running a governor’s mansion with three photogenic little children—a supporting role to the alpha-male husband with the Ivy League degrees, JAG tour in Fallujah, and presidential aura. But before any of that, Jill Casey Black was a chipper morning show anchor with First Coast News, which airs on both ABC and NBC affiliates in Jacksonville. For more than seven years, she commanded a loyal audience with local celebrity interviews and behind-the-scenes segments on military and criminal affairs, winning an Emmy for on-air talent, and two Emmy nominations for an investigative series, Real Life CSI, and a documentary about a disabled former football player. A dual degree econ major at College of Charleston, she later shifted into a producer role overseeing Jacksonville’s local version of The View, augmenting a natural sensitivity for the sorts of issues that resonated most with viewers.
Casey DeSantis stepped away from television in 2017, ostensibly to focus on her family while Ron, then a junior congressman, began exploring a run for governor. But she has continued to act as a producer of her husband’s political career, according to several sources close to the couple, helping to package far-right outrage over masks, vaccine mandates, and critical race theory for a MAGA-lite audience that might dislike Biden and loathe progressivism, but balk at QAnon election conspiracies. Ron first broke through as a national figure, after all, with his made-for-TV defiance of early-Covid public health restrictions, a libertarian stand that he parlayed into ubiquity on Fox News. Throughout the pandemic, he drew right wing praise over how he handled local mask mandates (prohibited), business shutdowns (absolutely not), and vaccine mandates (never, and he signed a law backing that stance).
Liberal condemnation for the governor’s rigidly laissez-faire approach was fueled by accusations that he misrepresented the number of Covid cases in Florida, which he repeatedly denied as media spin. But it’s the fight over public school education that has made the couple a fixture of the culture wars. With their focus on banning critical race theory concepts in K-12 classrooms, and a law aimed at preventing educators from referencing L.G.B.T. and gender identity topics in K-3rd grade classrooms, the DeSantii have carefully stoked a nationwide panic over parental rights—even managing to make an enemy of Disney, the largest employer in the state. Their aptitude for right-wing messaging is on par with Trump, but their brilliance is in calculating these provocations to resonate with a broader demographic of voters who don’t pay much attention to politics but are nonetheless hypersensitive about their kids.
And yet the DeSantii, for all their public bomb-throwing, are still something of an enigma inside G.O.P. circles—based in part on the not unfounded assumption that their rivals are out to get them. (Their latest Trumpian maneuver has been to endorse primary challengers against G.O.P. incumbents in the Florida Senate.) While they have been deliberately telegraphing their ambitions on the national stage, Casey and Ron have also maintained an unusually leak-proof operation that ensures that few people ever find out exactly what they plan to do before they do it.
Their message discipline is so stringent that even their internal emails reflect their talking points, and their inner circle is so tight that not even seasoned Florida insiders can tell who’s inside the DeSantis sanctum at any given moment. Indeed, multiple sources that I spoke to for this story told me that job applicants were required to sign an N.D.A. even before discussing the possibility of employment. The DeSantis team rarely, if ever, hires outside ad vendors and consultants, according to two DeSantis world insiders, preferring to do their political work in-house whenever possible. Even the junior staff are incentivized not to leak: I have never seen any campaign, much less a gubernatorial campaign, go out of its way to offer professional development and mentoring programs for young people.
An Audience of Two
Even those outside of DeSantis’s tiny circle of trust can easily identify Casey DeSantis as a full business partner and chief strategist. She occupies an office right next to Ron’s on the Plaza level of the State Capitol building, unusual real estate for Florida’s First Lady. She’s also a crucial part of the messaging team surrounding DeSantis, and has been ever since he was a back-bench congressman. And it’s said that she is still Ron’s primary advisor—to a level that goes beyond the typical politician’s My wife is my closest advisor talking point. “Everything had to be approved by her [when Ron was a congressman]. She would bug their comms staff to get him booked on TV. She edited and wrote talking points for him,” a Florida insider recalled. “The ‘18 campaign was a little bit different because it was so high profile, but she was still obviously intricately involved.”
And her instinct as a storyteller never went away. “I want to take a page out of Oprah’s playbook,” she told a local blog in Northwest Florida in 2019, a few weeks before Ron became governor. Casey was referring to the traits that make for a good interview, but the sentiment also speaks to her fascination with the power of media arts. “The kind of discipline it takes to be a TV person who then goes behind the scenes—that should never be underestimated, because that alone is a tremendous achievement,” observed the G.O.P. consultant. It also goes a long way towards explaining why she’s not a cable news defender of her husband, even though her on-camera expertise could prime her for the gig. Indeed, that job’s for a pundit, not an operative. (That job has gone to Christina Pushaw, whose ability to push back against “false Narratives about Florida & @GovRonDeSantis” keeps her tweeting against reporters 24/7.)
Befitting her public image as a member of the anti-M.S.M. DeSantis team—a notable percentage of their talking points center on how the mainstream media treats Ron unfairly—Casey DeSantis rarely goes on national conservative outlets, and barely speaks to mainstream press, even off the record. (Reporters who betray any sign of hostility, when placing a request for comment, may end up on the receiving end of Pushaw’s social media bazooka.) But virtually every single article about Ron DeSantis goes out of its way to emphasize how Casey has the human touch he seems to lack in public: the patience to empathize with voters on a rope line and keep smiling for hours; the charm to woo donors in private and make detractors blush; the stamina to make a Republican donor crowd go wild with a surprise appearance at a fundraising dinner, two months into chemotherapy for breast cancer. (As of March 2022, Casey is cancer-free.)
Imagining Ron DeSantis without Casey is a hypothetical without an obvious answer—a less charismatic law nerd, perhaps, or maybe a state senator. But DeSantis, who met Casey when he was a Navy JAG officer and she was a local crime reporter, has given some glimpses into their relationship during interviews with friendlier outlets. “What she understands is, ‘Look, you’re right on the policy, you can get this policy right on this bill, but so what? What does that mean for people’s lives?’” he told Sean Spicer on Newsmax in May 2021. “And you can never lose sight of that fact: it’s not just about signing a bill, or a budget item, or this and that. It’s: what does that mean?… What effect can you make in a positive way on people’s lives, and tell those stories, in what ways, that makes that resonate with folks?’”
The day before, Ron added, he’d signed a bill to expand school choice for low-income families. He’d made the announcement during a press conference at a local Catholic school that was, in fact, almost Oprah-esque: He trotted out two families to gush over the opportunities that the bill would give their children. Some of them were first-generation immigrants. Casey, who helped to orchestrate the event, was nowhere to be seen.
For the Kids
The emphasis on doing things for the children might seem trite, but in MAGA times, the classroom has become a major battleground for the culture wars, much like police headquarters, the role of the free press, and the concept of fair and secure elections. Arguably, it’s the most potent lever, angling straight into the hearts of parents who fear a fringe agenda to indoctrinate their children. Wearing masks in kindergarten? The kids don’t need it, and they might become little sociopaths one day if they keep covering their face. A vaccine mandate for their kids? That’s even worse. And the furor over the so-called “Don’t Say Gay” bill—initially a fringe lawmaker’s bill, before the most controversial language was stripped out—gave Team DeSantis an opportunity to surf the right-wing backlash to growing L.G.B.T. visibility and high-volume debates about pronouns.
“[DeSantis] could throw this back in their face and be like, No, it doesn’t say anything about ‘not saying gay,’ because the bill had been amended. But it was one of those things where he didn’t care about the bill,” explained the Florida insider. “It was somebody else’s priority. He only took the lead on that bill once the backlash from the Democrats started, [which] he, smartly, understood was sort of outside the mainstream of where the voters in Florida are. Certainly where Republican voters are, but really across the board.”
Indeed, a poll afterwards canvassed voters with the precise language of the bill: “Classroom instruction by school personnel or third parties on sexual orientation or gender identity may not occur in Kindergarten through third grade or in a manner that is not age appropriate or developmentally appropriate for students in accordance with state standards.” It found that an overwhelming majority of all voters—including Biden voters, Democrats, and people who knew L.G.B.T. people—supported the bill.
Did DeSantis have to go scorched earth against Disney by trying to punish their lucrative theme park empire? It’s still unclear whether that will be a meaningful gesture, let alone dent Disney’s bank account, but it signaled how serious he and Casey would be about pushing back the liberal tide.
Ronny & Nancy of Tallahassee?
The downside of building one’s political operation inside a black box, especially so close to the leaky worlds of Tallahassee and Mar-a-Lago, is that it leaves plenty of room for speculation in the form of gossipy tidbits leaked to reporters. The DeSantis office has been notorious for staff turnover, with people who might think themselves safe suddenly being put out to pasture. Why, for instance, would DeSantis freeze out Brad Herold and Susie Wiles, two of the campaign managers who helped him to eke out a narrow win over Andrew Gillum in 2018?
The Wiles firing has befuddled Florida Republicans, in particular. “There’s lots of theories about why it happened,” the Florida insider told me. “But for whatever reason, they just decided that Susie was their enemy, and they fired her and anybody associated with her.” (The DeSantis team declined to comment on the topic.) Wiles recovered dexterously—she currently runs the Save America PAC, Trump’s main political action committee—but Trump’s protective aura didn’t inoculate her from DeSantis’s ire. Back in 2019, months after Wiles had been pushed out of DeSantis World, Politico reported that Ron had convinced Trump to fire Wiles as his 2020 Floria advisor.
In the meantime, very few know exactly what Ron and Casey have planned after the November general election. What’s clear, however, is that the two of them are reshaping the state, bit by bit. At the moment, they’re pulling maneuvers to ensure that the Republican Party is full of DeSantis loyalists, and they recently launched the DeSantis Education Agenda, outlining the ideological requirements for any school board candidate who wants Ron’s endorsement. If anything, the need for absolute loyalty now extends beyond the DeSantis organization.
There is a downside to this insularity, of course. When Ron DeSantis eventually decides to test his popularity on the national stage, the DeSantii will have to deal with piles of resentful political staffers, lobbyists and politicians they’ve burned on the way up, shivved, or sharp-elbowed from close proximity. So far, DeSantis has been able to keep away from the fallout of Trump shenanigans and the MAGA rumor mill, deeply insistent that whatever happens on a national and international scale, outside of Florida’s borders and classrooms, does not pertain to him. (He’s got a state to manage, after all, and there is an undeniable benefit in not saying something that will inevitably be contrasted to Trump’s opinion.) The moment he steps onto the national stage, however, he will have to handle a barrage of issues outside the safe environs of the culture wars: a faltering economy, the rise of China, climate change, the war in Ukraine (which he has not much commented on) as well as the inevitable backbiting from anyone he’s burned. At that scale, villainizing CNN or The New York Times will not be enough.
But whatever the case may be, it’s undeniable that, in the way that former ABC executive James Goldston is stage-managing the January 6th Committee and Bill Shine, the former Fox executive, attempted to manage Trump, Casey will be working her magic on the grand scale.