The Ron DeSantis double play: A star ballplayer and a future politician

John Romano | The governor was a hit at Dunedin Little League and in high school long before he became a household name in Florida.
Florida Gov. Ron DeSantis, left, is seen in this 1991 photo when he played on the Dunedin Little League squad.
Florida Gov. Ron DeSantis, left, is seen in this 1991 photo when he played on the Dunedin Little League squad. [ PHOTO COURTESY OF JEREMY KURELLA | Photo courtesy of Jeremy Kurella ]
Published March 10, 2020|Updated March 10, 2020

NORTH PORT — The governor has a baseball card. I don’t mean a collection in the gubernatorial sock drawer, rather he actually appears on a baseball card.

It was part of a set put together to celebrate the Dunedin Little League All-Stars of 1991, the first team from Pinellas County to reach the Little League World Series since 1948.

There Ron DeSantis stands, aluminum bat on his right shoulder, staring into the camera with a look so assured it’s almost unnerving on a 12-year-old. D, as he was known then, was good. Darn good, really. Four of his teammates would go on to be drafted, yet it was DeSantis who pitched and hit in the middle of the order.

He was the kind of kid who might ride his bike to the ballfield off Harvard Avenue in Dunedin to stand alone by the fence and throw baseballs across the outfield to build up his arm strength. A kid who would sneak off with a teammate for a home run hitting contest on the eve of the World Series in Williamsport, Pa.

All these years later, the oddest thing about seeing their childhood friend on television riding on Air Force One with the president is that none of his old teammates find it remotely odd.

“I always knew he was going into politics,’’ said Brady Williams, who is now the Rays Triple-A manager in Durham and was then one of DeSantis’ closest friends. “His goal was to be the president of the United States. Was that far-fetched? A lot of things we talked about that summer were far-fetched. And a lot of them happened.’’

* * *

I recently accompanied DeSantis at the annual Governor’s Baseball Dinner at the Braves new spring training complex in North Port. Okay, accompanied is a stretch. It was more like stalking. Feebly, as it turned out.

Aides and friends promised they would get the governor to set aside 10 minutes to talk about his love of baseball. Just don’t approach him first, or that could blow the whole plan.

So I followed DeSantis around while he talked to Marlins manager Don Mattingly. And baseball commissioner Rob Manfred. And Braves chairman Terry McGuirk. And Hall of Famer Andre Dawson. And players from the Venice High state championship team.

DeSantis appeared to revel in the opportunity. As a fan, not a politician.

“We got him as a Little Leaguer,’’ Manfred said that night, “and we’ve had him ever since.’’

As a kid, DeSantis didn’t just play the game, he soaked it up. Long before the Devil Rays arrived, he watched the Braves on TBS and Cubs on WGN.

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His baseball coach at Yale, where DeSantis was a four-year starter and captain of the team as a senior, said he was one of the few players he ever had with a wide knowledge and appreciation of the game’s past.

Orioles general manager Mike Elias, whose playing days at Yale did not overlap with DeSantis, has grown friendly with him over the past 20 years. “I think it’s a fun part of his job to preside over a state with spring training," Elias said, "because he still follows Major League Baseball very closely.’’

* * *

That summer of ’91 was nearly perfect, and so were the boys of Dunedin Little League. There was something remarkable about their devotion. To the game. To each other. To this crazy notion they could reach the Little League World Series.

“We set out from the beginning of the season to make the World Series,’’ said Nick Tsotsos, now a business teacher at Safety Harbor Middle School. “We were definitely your normal 11- and 12-year-olds, but it was an intense summer. That whole summer there might have been two days where we weren’t playing or practicing baseball.’’

And, of course, they kept winning. And dreaming. And they never doubted for a minute that their third baseman/pitcher was dead serious when he said he would one day be president of the United States.

And why not? Was it really that much crazier than a handful of kids from Dunedin reaching the World Series in Williamsport, Pa.?

To them, DeSantis was wicked smart with a cool confidence. When the players gathered for breakfast, he would read stories aloud from the newspaper, comically substituting his own version of events at the expense of an unsuspecting teammate.

When they played friendly games of Wiffle ball against other Little Leaguers at the World Series, they wanted Taiwan’s top pitcher to stay on the mound the whole game, hoping to wear out his arm.

“D was brilliant,’’ said Jeremy Kurella, now a Pinellas County deputy and resource officer at Palm Harbor University High. “I never doubted that he could be president.’’

He hasn’t moved into the White House just yet, but give DeSantis time. He earned degrees from both Yale and Harvard, served in the Judge Advocate General Corps (JAG) of the Navy and won three terms in Congress before becoming governor of Florida.

As it turns out, winning elections was more plausible than winning the World Series. Dunedin lost the opening game, 5-4, to California, came back through the losers’ bracket, but was eventually eliminated, 3-2, by the Dominican Republic. DeSantis had four hits, including a home run, and struck out 11 in five innings to earn the win in their lone victory.

“I think that summer taught us something,’’ said Jay Frazer, a regional manager for a medical management service in San Francisco. “If you’re willing to put your nose to the grindstone, you can always dream big.’’

Those players went on to challenge for state and regional titles in youth leagues for the next three summers as they moved up in age groups. A half-dozen of them ended up at Dunedin High, where they lost the Class 5A state championship game to Naples-Barron Collier in 1997.

DeSantis was second-team All-Conference as a sophomore and hit .327 as a senior despite missing much of the season with a thumb injury. Along the way, DeSantis coached one of the powder puff football teams at Dunedin — and won.

“Whatever he put his mind to, he would immerse himself in it,’’ said Frazer, who was part of a mock debate team with DeSantis at Dunedin High. “He had talent, focus, determination. There was definitely some special sauce in there.

“If you called me back in 10 years, I wouldn’t be surprised if we’re talking about how he became president.’’

* * *

After nearly three weeks of emails and phone calls — and one night debating whether to nudge his elbow during his barbecue dinner in North Port — the governor’s office declined to make him available to talk about baseball not even for 10 minutes. His staff did email two bland quotes.

Even so, the portrait of a man still in love with baseball is not difficult to draw. In his final summer in the House of Representatives, DeSantis played in the Congressional Baseball Game after missing a few years due to injuries. Hitting cleanup for the Republicans, he stroked a line drive to the opposite field for a single in his first trip to the plate. He grounded out in his second at-bat, and then ripped a single to leftfield in his third.

He spends more time on the golf course than a baseball diamond these days, but his Yale jersey is framed and hangs in his office at the state Capitol.

Related: More from Tampa Bay Times sports columnist John Romano

DeSantis hit .313 in his four years at Yale, but he wasn’t a pro prospect. The arm was too weak, and there wasn’t enough offense to offset the deficiency.

Besides, DeSantis had his eyes set somewhere else.

Yale coach John Stuper remembers telling a writer once that DeSantis would be someone to watch, away from the field.

“I think the world of Ron DeSantis. He’s got integrity through the roof. I couldn’t be prouder of him," Stuper said. "You don’t think I tell every recruit who walks through the door that I coached the governor of Florida?’’

John Romano can be reached at Follow @romano_tbtimes.