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Casey DeSantis Has Taken Florida Politics By Storm

The Ohio native and former TV host has captured the attention of Florida residents, making her an especially powerful asset to her husband’s 2024 presidential campaign. But some wonder if the couple will be enough to sway an entire nation.

the DeSantis family
From left to right: Florida Gov. Ron DeSantis, Mason, Madison, Casey DeSantis and Mamie wave to the crowd during an inauguration ceremony at the historic Florida Capitol on Jan. 3, 2023, in Tallahassee, Florida.
(Matias J. Ocner/Miami Herald/TNS)
(TNS) — Attendees of a Hernando County, Fla., Republican Party dinner paid up to $350 each to hear the governor speak ahead of his 2022 reelection. But their cheers turned into wolf whistles and shrieks as Casey DeSantis stepped out in a surprise appearance.

It was just days after the public learned that the first lady had been diagnosed with breast cancer.

While Gov. Ron DeSantis looked on, his wife cracked a joke about the standing ovation starting before she’d even entered the room. Then the audience fell silent, rapt, as she addressed the weight of the moment.

“I’ve done a lot of thinking, obviously, as of recent. I think there’s a lot we can be upset about,” she said, her voice sometimes wavering. “The direction of our country … our children, their education, their futures — our health and our well-being. But I tell you, one thing is for sure: I’m sure as hell not giving up.”

The crowd erupted.

As Gov. DeSantis stands at the precipice of his biggest political undertaking yet — a widely expected run for president — Casey DeSantis is by his side, lending poise to his political muscle. Insiders know her as a singular partner in weighing her husband’s maneuvers at a moment his administration holds state government in a firm grip. Once called a “secret weapon,” she is no longer under the radar.

Trained as a TV journalist and talk show host, Casey DeSantis is practiced in the art of improvising before an audience. With a gentle joke or anecdote about the kids, she infuses warmth and mom-next-door relatability into the governor’s pugilistic, sometimes awkward brand.

“She is a powerful force,” said U.S. Rep. Jared Moskowitz, a former DeSantis administration official. In a presidential campaign, he said, the first lady would be “an absolute X-factor.”

“Nobody else who has been mentioned on the Republican side has a Casey DeSantis,” he said.

In an administration with fairly high turnover and a famously small circle of trust, the first lady is DeSantis’ closest confidant. At donor dinners, she impresses. Onstage, she catches eyes in Republican red. Her fingerprints can be seen on her husband’s media strategy, his campaigns — even his inner circle.

Stephen Lawson, a former spokesperson for the governor’s 2018 campaign who now runs a Georgia political strategy firm, put it this way: “In many instances, the sounding board starts and stops with Casey.”

From Ohio Town to Jacksonville Airwaves

Jill Casey DeSantis, 42, grew up in middle-class Troy, Ohio, a manufacturing hub half an hour from Dayton. Hers was the largest town in a stubbornly Republican county — one that stayed red amid the state’s blue swings.

Her father, Robert Black, was an optometrist, and her mother, Jeanne, a speech pathologist at the elementary school that Casey and her sister, Kate, attended. Sandy Gurklies, a family acquaintance who works at the local history library, said Casey rode horses competitively, while Kate spent mornings at the ice skating rink.

As the Tampa Bay Times set out to profile Casey DeSantis, neither the first lady nor the governor agreed to an interview. Her parents, who live in South Carolina, could not be reached. While a woman confirmed that a reporter had indeed dialed the Blacks’ residence, she declined to take a message before hanging up. The Times also did not receive cooperation from the governor’s office or his political team. But, from interviews with people who knew her before she became first lady, political operatives who’ve seen her in action and officials in the DeSantis orbit, a portrait emerges of a woman tenacious in her pursuits, with a natural ability to charm. The first lady is also said to share her husband’s guardedness about whom she can trust.

Casey DeSantis invoked her father at a campaign stop last summer — her first after doctors declared her cancer-free.

“Ever since I was very little, he would call me and he would say … ‘Casey, have faith, and don’t let the bastards win,’” she said.

Casey DeSantis has gone by her middle name since at least her high school days. Photos of her dot pages of her yearbooks: running relays, playing varsity basketball, planning dances, grinning on homecoming court, serving as student council treasurer and as a “D.A.R.E. role model.”

At the College of Charleston in South Carolina, she studied economics and French. She rode on the college equestrian team and placed runner-up at the Division I NCAA National Championships, according to her state bio. Then she decided to go into journalism.

In addition to a stint at the PGA Tour as a producer and on-air host, she worked for TV stations in Jacksonville. Her roles included police beat reporter, weekend anchor and the co-host of a daytime talk show called First Coast Living. Years later, as her husband’s political ambitions grew, she would step down to help with his campaign for governor and be with their two kids, Madison and Mason. (A third, Mamie, would be born after he was elected.) But in her days on air, a colleague said, she was a pro, putting nervous interviewees at ease.

“There’s just people in the TV industry, that do on-air journalism, that have that natural delivery ... watching them, listening to them is easy,” said Nikki Kimbleton, who was a fellow morning anchor at News4Jax. “To this day, she’s one of the best I’ve ever worked with.”

Casey DeSantis met her future husband in 2006 at a driving range in Jacksonville, after they struck up a conversation over a bucket of golf balls. In his new book, the governor called the encounter “my life’s most fortuitous moment.”

Kimbleton remembers sensing they would end up together, after her friend told her “she met this guy that had terrific potential.”

Three years later, Ron DeSantis donned his Navy dress whites as the couple married at Walt Disney World, with a fairy-tale reception at Epcot. (Gov. DeSantis has recently been locked in a political brawl with Disney.)

DeSantis has quipped that the wedding locale came at the request of the bride’s parents, whom he described as “big Disney enthusiasts.”

It was Casey who encouraged her husband to leap into politics, according to DeSantis’ most recent book. He said supporters raised the idea of him running for an open northeast Florida congressional seat in 2012 while he toured for his first book, a jab at then-President Barack Obama’s policies.

At the time, Ron DeSantis, then a civil lawyer, didn’t have name recognition or the wealth often needed to take on a competitive Republican primary. He and Casey split up neighborhoods to knock on doors, and she rode a $50 Walmart bicycle until its handlebars fell off, she once told a crowd. Gov. DeSantis wrote that her TV star power made her a “major force multiplier.”

He won the seat.

An Eye for Messaging

Not long after DeSantis was elected governor, the new first lady of Florida traveled through the slanted pines and bare foundations of a Panhandle ravaged by Category 5 Hurricane Michael.

Riding in an SUV, she read through binder after binder of material for the days’ events — touring disaster areas, meeting with teachers, announcing mental health resources — and went back and forth with staff to check her facts. Typically, Rep. Moskowitz said, she did so with a pen in hand, wanting her remarks to say things “in a more relatable way.”

“This is someone who had a real command of communications,” he said. Moskowitz is a Democrat and was a surprise pick to lead the state emergency management division in the first few years of DeSantis’ administration.

In mid-2020 into 2021, while Gov. DeSantis moved to aggressively reopen the state from pandemic closures, he faced an avalanche of critical coverage as health experts questioned his approach. The governor and other top officials felt singled out compared to leaders of blue states.

The administration’s relationship with journalists, always distant, increasingly hardened.

The governor began calling out reporters whose stories he found unfair, while the administration hired communications staffers who proved highly combative.

Casey DeSantis, once sympathetic to the pressures of the media industry, changed her strategy to hit back harder. In a Fox News town hall last year, she had harsh words for her former profession.

“I don’t think people buy what the woke corporate media is throwing at them anymore,” she said. “(The governor) was right through COVID. And a lot of the media who were wrong, they’ve never apologized for being wrong.”

During the 2022 midterms, DeSantis’ team ran a barrage of ads, fueled by a seemingly endless flow of money to his record-breaking reelection campaign. (The first lady is said to pay close attention to campaign expenses.)

Arguably the most talked-about ad was one that featured only Casey DeSantis.

Cross-legged on a couch in a periwinkle sweater and jeans, she begins: “I get asked all the time: Who is Ron DeSantis?”

“When I was diagnosed with cancer, and I was facing the battle for my life, he was the dad who took care of my children when I couldn’t. He was there to pick me off of the ground when I literally could not stand,” she says, emotion seeping into her voice. The camera slowly zooms in on her face.

The music fades.

“He was there to fight for me when I didn’t have the strength to fight for myself. That is who Ron DeSantis is.”

She filmed it unscripted.

The DeSantis One-Two Punch

Last July, over the clinking of silverware, the governor and first lady appeared at the Moms for Liberty conference in Tampa.

The governor spoke first, railing against Disney and other corporations’ “stupid activism” and the threat of “woke” school lessons: “We should not be spending tax dollars or using our energy to teach our kids to hate our country or to hate each other.”

Not long after, Casey DeSantis took the stage with her then-5-year-old daughter, Madison. She characterized her husband’s agenda as “empowering parents.”

“Our kids, they are the ones who are going to inherit the republic,” she said.

Madison repeatedly tapped her mother’s arm. The first lady continued speaking, unfazed, taking hold of Madison’s hand, while mothers in the audience chuckled knowingly.

Many observers view Casey DeSantis’ greatest contribution politically as her ability to humanize the governor, who has a reputation as a culture warrior uneasy with schmoozing or being overly warm, even with his own staff.

For instance, Gov. DeSantis pushed the Special Olympics to drop its COVID-19 vaccine requirement for competitions in Orlando. In his words, Florida was fighting for “people who didn’t bow down to the altar of these vaccines.”

The same message, delivered with Casey’s touch, underneath an Instagram photo of her husband with a young athlete: “Isabella’s smile says everything.”

At the Moms for Liberty conference, Angela Dubach, the group’s Pinellas chapter chairperson, marveled at the first lady’s approachability and Jackie Kennedy Onassis-like glamour. Dubach said she imagined her as a woman who might strike up a connection, asking: ”’Hey, how are you doing? Do you want a cup of coffee?’ Or, ‘Let’s go get a drink!’”

The first lady’s offshoot of the governor’s reelection campaign, “Mamas for DeSantis,” ultimately signed up more than a million people.

Exit polling by CNN suggests that Gov. DeSantis won the women’s vote in the state, a flip from two years earlier, when Florida women supported President Joe Biden.

Candidates’ spouses have long been considered key to providing voters with rare insight into politicians’ personal lives.

In recent Florida history, Casey DeSantis stands out. Ann Scott, who had a fear of public speaking, stayed out of the spotlight during now-Sen. Rick Scott’s first run for governor, and during her tour of the state for his 2014 reelection, she avoided policy talk. Columba Bush also shied from politics, only stepping out more once former Gov. Jeb Bush started running for president, and even then often focused on her preferred issues.

High-dollar donors have taken note.

Ken Jones, CEO of Tampa investment firm Third Lake Partners LLC, has hosted fundraisers for DeSantis around the state. In those intimate settings, he said, the first lady shines.

“If you are asking people for money, you need to be able to have a command of the issues that those people care about and have a real understanding of what motivates and drives people,” he said. “She has all those things.”

At a “Mamas” event in Sarasota, “hundreds of people showed up — just for the first lady,” said Christian Ziegler, who leads the Republican Party of Florida.

Afterward, he said, people raved: They believed in her.

“You know when all the staff leaves, and the door shuts, and dinner is over, and the kids are in bed, (Ron and Casey DeSantis are) sitting at the couch and talking about the things he’s facing,” Ziegler said. “To have that much confidence in her gives that much more confidence in him.”

Of course, there’s a limit to how much Casey DeSantis may be able to fill the governor’s retail politicking gaps in a presidential race, where candidates are expected to go on camera from Midwestern diners and the steak fry in Iowa.

“Ron is not a natural, charismatic politician. His interpersonal skills tend to be more introvert than extrovert,” said David Jolly, who served alongside DeSantis in Congress and has since left the Republican Party.

“At some point, if DeSantis is the nominee, he’s going to have to do the Lester Holt sit-down for the country to see who he is, and stand up in debates in front of an objective press,” Jolly added. “Can he survive the bright lights of the big stage?”

The First Lady’s Fingerprints

On the ground floor of Florida’s Capitol building, beyond where the public is permitted to roam, lies Gov. DeSantis’ wood-paneled suite — the Oval Office of Florida government.

Doors inside lead to adjoining offices: One is the chief of staff’s. Another, larger office has belonged to Casey DeSantis.

She’s used it for meetings on her initiatives, which center on mental health, child welfare, cancer research and other issues.

“She obviously has a very special lens through which to view people’s well-being,” said state Surgeon General Joseph Ladapo, referencing her cancer diagnosis.

The first lady has spearheaded fundraising for a state disaster fund for Hurricane Ian recovery, which she said in February had doled out about $45 million with millions more to go.

“She’s not afraid to walk the halls of the Capitol and talk with members of the Legislature about these issues,” said Rep. Sam Garrison, R-Fleming Island, reflecting on the first lady’s support for youth mental health.

Hillsborough Sheriff Chad Chronister, who has met privately with the first lady to talk policy, agreed: “It became abundantly clear from the beginning that she has a passion for children.”

There is also her influence on the governor’s circle.

Susie Wiles, a GOP strategist and veteran of Donald Trump’s Florida campaign, helped rescue DeSantis’ struggling 2018 bid for governor. After he eked out the win, Wiles took a leading role in DeSantis’ transition into office.

Not long into DeSantis’ first term, though, documents obtained by the Tampa Bay Times showed a plan to sell rounds of golf or dinners to special interests seeking access to the governor. DeSantis allies blamed Wiles for the leak, and she was swiftly ostracized.

Politico reported that the first lady was one of the top advisers suspicious of Wiles.

“On the one hand, she wants to be, ‘I’m just a mom, I’m just Ron’s wife.’ On the other hand, ask Susie Wiles how she feels about Casey DeSantis,” said Rick Wilson, a longtime Florida Republican political strategist. He has since left the party and co-founded The Lincoln Project, an anti-Trump group that also opposes DeSantis. “You’ve got to play one role or the other: You’ve got to be the devoted spouse … or ferocious political counselor and yielder of knives.”

Wiles did not respond to a call or text seeking comment. She’s working once more on Trump’s team.

“The story of Casey and Susie is not pretty,” Wilson added. “I’m sure it’s going to get rolled out by a guy who lives in Mar-a-Lago in the near or immediate future.”

In his latest book, “The Courage to Be Free,” DeSantis says his administration has no tolerance for leakers and “petty drama.”

In the acknowledgments, the governor thanks his wife for her edits and her hand in his success.

Perhaps more telling is the dedication page.

“To Madison, Mason, and Mamie,” it reads. “Remember to always listen to your mother.”

©2023 Tampa Bay Times. Distributed by Tribune Content Agency, LLC.
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