At Dunedin High School, classmates knew him as a super jock and a brilliant student.
At Yale, the baseball coach barely hesitated naming the former team captain when an interviewer in 2002 asked if he had ever managed someone of presidential material.
Now running for Florida governor, Ron DeSantis, 39, has won the backing of President Donald Trump and billionaire donors across the country, and by many accounts is the most likely Republican nominee to lead America’s third-largest state.
“I’m getting calls from people who are supporting Adam Putnam for governor, but they also want to give to Ron,” said Nancy McGowan, a conservative activist raising money for DeSantis in the Jacksonville area. “And people tell me, ‘I’ve committed to Adam, but I think Ron’s going to win, and I’d like to talk to him.’ ”
DeSantis’ personal story helps drive the buzz. Dunedin’s Little Leaguer went from Yale to Harvard Law, becoming a decorated military lawyer who deployed with the Navy Seals in Iraq and was elected to Congress.
Since entering politics six years ago, DeSantis has bounced from race to race, leaving few tangible accomplishments over his steady political rise as a Fox News favorite and pitbull Trump defender. Even some admirers question his credentials for governor and think he’s more attuned to the ideological battlefield of Washington.
The son of a nurse and a Nielsen TV ratings box installer is following the lessons he learned in 1991 leading his team to the Little League World Series: Set big goals, and then leave it all on the field in pursuit of them.
ESTABLISHING A REPUTATION
With the TV cameras rolling in December, Congressman DeSantis grilled Deputy Attorney General Rod Rosenstein. In college he liked to recite lines from “A Few Good Men,” but with his brow furrowed and a disdainful tone, the former Navy JAG showed more confidence than Tom Cruise that afternoon.
“Did the FBI pay for the dossier?” DeSantis pressed, referring to the controversial intelligence and opposition research report alleging misconduct and conspiracy between the Trump campaign and Russia.
Rosenstein: “I’m not in position to answer that question, congressman.”
DeSantis: “Do you know the answer to the question?”
Rosenstein: “I believe I know the answer, but the intelligence committee is the appropriate committee to make that …”
DeSantis: “That is not true. We have oversight over your department and the FBI, and whether public funds were spent on a dossier, that is not something that’s classified. We have every right to that information. You should provide it. Was that info used to get surveillance over anybody associated with Trump?”
The performance energized conservatives on social media. Clips like that — as well as DeSantis’ near-daily appearances on Fox News attacking the FBI and Special Counsel Robert Mueller — have established him as an unbending supporter of Trump and advocate for conservative priorities.
The publicity made him a favorite of tea partiers, Trump supporters, media figures like Sean Hannity and Mark Levin and the president.
“Congressman Ron DeSantis is a brilliant young leader, Yale and then Harvard Law, who would make a GREAT Governor of Florida. He loves our Country and is a true FIGHTER!” the president tweeted a few days before Christmas.
In classic Trump form, he was watching a Fox News segment featuring DeSantis while flying on Air Force One to Palm Beach for the holiday. A couple of weeks before, DeSantis hitched a ride with the president to Pensacola for a campaign-style rally.
A curious thing about DeSantis: He is an eager and tireless charmer of conservative national media figures and the country’s richest conservative donors, but he has few friends among colleagues in Congress.
Lawmakers privately describe him as aloof and a bit of a know-it-all. He has engendered little loyalty from former staff, who consider him self-centered. And DeSantis has seemed uninterested in Florida issues or chatting up colleagues, especially anyone who’s not a member of the Freedom Caucus, the most conservative and uncompromising members of the House.
He routinely ignores policy questions from Florida reporters and would not comment for this story.
A stocky figure with swept-back brown hair, DeSantis often walks the Capitol hallways wearing ear buds or talking on the phone, effectively fending off chitchat with other members. But he assiduously courts his rich benefactors, checking in regularly. He sleeps in his office.
“He kept to himself,” said former U.S. Rep. David Jolly, R-Belleair Bluffs, who ran against DeSantis for the Republican U.S. Senate nomination in 2016 until Marco Rubio decided to seek a second term.
“I don’t know that I ever saw him speak up at [Republican] conference meetings. It was a serious quality he had, not a loner quality. He’s cerebral, with a very strong ideology,” said Jolly, who viewed DeSantis as the smartest and best qualified of his four Senate primary rivals.
“Don’t underestimate him,” Jolly added. “He’s very skilled, he’s very smart, he’s very disciplined, and I imagine he already has his strategy and pathway determined and will abide by it all the way through the primary.”
AN EARLY STANDOUT
Everybody called him “D.” Even Little League opponents as he stepped into the batter’s box in July 1991.
“D! D! D!” preteens from Seminole mockingly chanted at a championship game. He blasted a two-run homer, batting .720 in three tournament games.
Classmates at Our Lady of Lourdes Catholic School and Dunedin High paint a Norman Rockwell picture of DeSantis’ youth. Kind, loving parents raised him and his younger sister in a 1,500-square-foot ranch. The kids excelled in most everything, and Ron took a particular interest in history.
“He was friends with kids in all kinds of different groups,” said Rebecca Zoumberos, a classmate who served on the homecoming court with him. She expects to vote for him: “I know him and his character. He’s one of the good ones.”
Yale baseball coach John Stuper says DeSantis stood out on the field (a four-year starting outfielder and .313 hitter, compared to .230 for another former Yale team captain, George H.W. Bush), and off. Among the many privileged Yalies, DeSantis worked as an electrician’s assistant and baseball camp coach and took other odd jobs to cover expenses.
“You look at his transcript his last two years, there wasn’t a B on it. How he could work 20 hours a week at baseball, probably that many hours a week at various jobs and still kill it in the classroom like he did is pretty amazing,” Stuper said.
Former Red Sox pitcher Craig Breslow was elected captain the year after DeSantis.
“We saw the traits that made him successful later on pretty early in college,” Breslow said. “His pedigree is pretty impressive — Yale, Harvard Law — but that shouldn’t be misleading. He grew up with blue-collar roots and has the ability to relate to anybody.”
At Harvard, DeSantis began to earn notice in conservative circles through involvement with the Federalist Society, an influential network of lawyers.
“I certainly became introduced to him through that, and I suspect a lot of other people did, too,” said Leonard Leo, executive vice president of the group in Washington.
Leo said DeSantis has a rare ability — he likened him to ardently conservative Sens. Ted Cruz of Texas, Tom Cotton of Arkansas, and Mike Lee of Utah — to boil down complex, esoteric conservative principles and capture broad public attention.
A cum laude Harvard Law degree is a ticket to virtually any job. DeSantis chose military service, joining the U.S. Navy Judge Advocate General’s Corps while at Harvard.
“You gravitate toward a handful of people and a handful of people end up taking leadership roles. Ron was one of those,” said Nevada Attorney General Adam Laxalt, DeSantis’ roommate at Naval Justice School in Rhode Island and a Republican candidate for governor there.
DeSantis worked at Naval Station Mayport in Jacksonville, where he met his wife, local television host Casey Black. (They have a daughter and another child on the way.) He served at the terrorist detention center at Guantánamo Bay, Cuba, and in 2007, he volunteered for and won a coveted and highly competitive assignment with SEAL Team One, deploying to Iraq.
Helping advise the SEALs on rules of engagement, such as when to shoot and whether to go into certain areas, DeSantis deployed to Fallujah as part of the troop surge. He earned a Bronze Star (meritorious service), usually reserved for senior officers.
Outside of his Federalist Society activities, friends say DeSantis’ conservatism and interest in politics rarely surfaced in high school, college or his military career. He has said it rose from a lifelong passion for history and studying the Founding Fathers.
The tea party movement was exploding as DeSantis left active duty, and he turned his attention to a political career.
‘A DIFFERENT DIRECTION’
After exploring a run for state House, DeSantis in early 2012 pivoted to an open congressional seat in the Jacksonville area, joining a crowded Republican primary with better-known candidates.
But DeSantis had powerful factors in his favor: the military record, Ivy League connections and conservative bona fides from a book he wrote in 2011, “Dreams From Our Founding Fathers: First Principles in the Age of Obama.” The book excoriates the president as a European-style leftist abandoning the principles of the founding fathers.
DeSantis hawked the self-published book at tea party gatherings, while contacts from Yale and Harvard provided early fundraising.
“He came to my attention because he’s a Yalie,” said Joseph Fogg, a 1968 graduate who led financial firms and now lives in Naples. Fogg hosted early fundraisers for DeSantis, impressed by his strong views about Obama. “Those of us on the conservative side of the ledger were looking for some bright young people that would be taking the country in a different direction.”
Fogg is supporting House Speaker Richard Corcoran in the race for governor, saying he’s gotten to know the speaker through work as a trustee for Florida Gulf Coast University and thinks Corcoran has command of state issues. “I still highly respect Ron. I suspect what he really would have preferred to do is run against Bill Nelson. But that path is blocked” by the expected challenge from Gov. Rick Scott.
Another Yale connection, former DeSantis roommate Nick Sinatra, provided inroads to Trump. Sinatra worked on Carl Paladino’s 2010 gubernatorial campaign in New York alongside Roger Stone, who composed a tweet that Trump fired off on March 20, 2012: “Ron DeSantis, Iraq vet, Navy hero, bronze star, Yale, Harvard Law, running for Congress in Fla. Very impressive.”
It was Fox News — advertising, not appearances — that brought DeSantis from obscurity in his first campaign. His team gambled on heavy advertising while DeSantis began to walk neighborhoods and introduce himself to voters.
It began to pay off in polls, and that summer DeSantis was taken to Washington for a round of meetings with conservative groups, including FreedomWorks, Heritage Foundation, the U.S. Chamber of Commerce and the Club for Growth.
Crucial to that endeavor was Daniel Faraci, a Washington lobbyist and campaign consultant who helped prep DeSantis and pitched the candidate as rock solid ideologically.
During a sit-down with the Club for Growth, DeSantis impressed with a command of the Bill of Rights and the issues. The book helped, too. “Right off the bat he was scoring positive points with us,” said Andy Roth, a club vice president. “It was a no-brainer that we endorsed him and then, as they say, the rest is history.”
The first FedEx full of checks provided resources to buy more ads, including attacks on primary rivals, who complained they were misleading or false. The club’s wealthy members kicked in more than $100,000 and have since contributed $500,000 to DeSantis’ campaigns.
He won the GOP primary by 16 percentage points and easily dispatched a Democrat in the general election.
LEGISLATING VS. IDEOLOGY
In Congress, DeSantis immediately showed his conservative backers where he stood: One of his first votes was against billions in disaster relief to help New York and New Jersey rebuild after the devastating Hurricane Sandy. DeSantis said it spread the spending over too many years and was not offset with budget cuts to other government programs.
Legislating appears less important to him than ideology.
He pushed for term limits and turned down the congressional pension and health insurance, explaining he was trying to lead by example. Few members have followed him. In 2015, DeSantis helped form the Freedom Caucus, a coalition of archconservatives that forced Speaker John Boehner into retirement. He has favored measures that would scale back billions of dollars in government support for the domestic sugar industry, putting him at odds with powerful forces in Florida.
Most prominently, he has questioned the investigation into Russian meddling and the Trump campaign. In August, he floated an amendment to a spending bill that would have cut off funding for Mueller’s investigation. It was not adopted, but it ensured DeSantis time on Fox News.
DeSantis also has touted his advocacy for moving the U.S. Embassy in Israel to Jerusalem, a move long sought by members of both parties and a campaign pledge of Trump’s that he recently acted on.
WHAT’S HIS STAYING POWER?
In five years, DeSantis has run for Congress, for U.S. Senate, for Congress again in a different district, and now for governor.
“DeSantis always gave the impression he was just biding his time until he made his next move,” read a Jan. 30 editorial in the Daytona Beach News-Journal that expressed relief he was moving on. “Like an ambitious college graduate working his first entry-level job, you knew he was gone as soon as he felt he had accumulated enough experience to ascend to the next rung on the ladder.”
The editorial said it was appropriate DeSantis announced for governor in a Fox News studio in New York, then kicked off his campaign in Boca Raton, 200 miles from his district, then talked a lot about federal issues. “But it was in keeping with a congressman whose press releases more often trumpeted his position on an investigation of Democratic policies than funding for a local project.”
He drew criticism from GOP opponents in his U.S. Senate campaign for missing votes to raise funds. Last year, he missed 53 of 710 votes, tying him for 50th-most absent member of the House. On Wednesday, he skipped a few minor votes to attend a fundraiser in Jacksonville. Those demands will only grow as the campaign matures.
The staying power of his deeply conservative record remains an open question.
Gwen Graham, the front-runner for the Democratic gubernatorial nomination, voiced the view of many Florida Democrats sizing up the prospective Republican nominees.
“Please give me Ron DeSantis,” she said at a recent fundraising reception in Tampa.
Even some Republicans say he needs to demonstrate aptitude for the job.
“Ron is going to have to prove in the campaign that he’s capable of being CEO of an extremely large state,” said Rep. Tom Rooney, a Republican from Okeechobee who has gotten to know DeSantis through the congressional baseball team but is backing Putnam.
“His bailiwick has been national security and foreign affairs,” Rooney said. “Being the governor, you have to convince me that you’re going to be the best person to deal with school issues, healthcare issues, welfare issues, safety during hurricane season, things like that, more than just being the guy endorsed by the president.”
Times senior researcher Caryn Baird contributed to this report.