Early last year, two political adversaries slid into a booth at the back of a Panera Bread in South Tampa for an extraordinary meeting.
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A decade earlier, Alex Sink and David Jolly faced off in a bruising race for a Pinellas County congressional seat. Jolly, then an upstart Republican, narrowly defeated Sink, a well-known politician and member of the state’s Democratic establishment.
Now, over coffee, Jolly laid out his ambition to run for Florida’s highest public office — as a Democrat.
Sink was intrigued; she had seen him on MSNBC chastising President Donald Trump and been impressed. But as a former gubernatorial candidate herself, she knew how difficult a statewide campaign would be.
So after Jolly finished his pitch, she gave him blunt advice. “You’re going to need to do better,” she said.
Almost 18 months later, Jolly resoundingly won the Democratic nomination on Tuesday with more than 60% of the vote. He gained traction in the polls, building a lead of more than 40 percentage points by this summer.
The decisive victory was no small feat for a candidate who once worked as a corporate lobbyist for defense contractors and later voted against the Affordable Care Act.
In interviews, Jolly, 53, and some of his close advisers said that the campaign had followed the guidance of key Democratic strategists and stepped up when other prominent politicians stayed on the sidelines.
“I got in early and did the work of meeting with Democratic groups before anyone else did,” Jolly said. “When others looked into getting in the race, I had already locked up support.”
Most of all, Jolly convinced enough Democrats that he was one of them and capable of doing something that Democrats haven’t done in 32 years: win the governor’s race.
“He’s good at feedback,” Sink told the Tampa Bay Times. “And he’s disciplined. He won over people one at a time.”
Outcast to pundit
The road to Jolly’s unlikely gubernatorial campaign began more than a decade ago on Capitol Hill.
As a Republican member of Congress, Jolly had a reputation for casting moderate votes and occasionally breaking ranks with the GOP. He defended Planned Parenthood. He pushed for tighter gun control and opposed offshore drilling. He was also an early critic of Trump, who was then running for president.
His time in Congress did not last long. He was defeated after one term in 2016 by Charlie Crist, a former Republican who ran for the seat as a Democrat. Jolly found himself in the political wilderness.
He remained there after flirting in 2018 with running as a Republican lieutenant governor on a Unity Ticket with Democrat Patrick Murphy for governor. Later that year, Jolly announced on HBO’s “Real Time with Bill Maher” that he had left the GOP and registered himself with no party affiliation.
As a steadfast anti-Trumper, Jolly continued to pursue a third way in American politics. In 2022, he founded the Forward Party with former Democratic presidential hopeful Andrew Yang and former Republican New Jersey Gov. Christine Todd Whitman. That, too, fizzled.
As his political career stalled, Jolly’s career as a pundit thrived. He was an MSNBC fixture, appearing regularly on “The Rachel Maddow Show,” along with other NBC programs such as “Morning Joe.”
“People want authenticity, their radar is strong,” Jolly said. “TV allowed me to find that gear. I was in people’s homes during some big moments, impeachments, school shootings. That gave me credibility to be considered a candidate.”
He struck up a friendship with another commentator on MSNBC, Democratic strategist and pollster Fernand Amandi.
“David always impressed me as kind of a throwback Florida figure, the type of politician in the mold of (former Florida Gov.) Reubin Askew, who put the state above partisanship,” Amandi said. “I thought he’d be a great candidate.”
But it wasn’t clear when that might happen. As 2024’s election night ended, Jolly told his wife, Laura, they could stop talking about a governor’s run.
Trump had just won Florida by 14 points.
‘Something is changing’
In the dead of winter in early 2025, Jolly spent more time at 30 Rockefeller Plaza in Manhattan as he focused on his TV career. Then something unexpected began to happen. Democrats were winning special elections — in places where Trump had won. Jolly studied the turnout and polling data. He said he concluded that Democratic despair had hardened into resistance.
One day, his friend, Amandi, texted him: Don’t rule out a run.
“He told me, ‘Something is changing,’” Jolly said.
“It was a combination of the moment, the man and the opportunity,” said Amandi, who teaches political science at the University of Miami. “The talents I saw in Jolly I saw taking hold in this environment.”
Amandi said he and Jolly already knew the campaign slogan.
“I told him in late January, ‘Make Florida Affordable Again,’” he said. “He was the first candidate to talk about it, and sure enough, that was the issue.”
Thanks to his name recognition from MSNBC, Jolly was invited to speak all across Florida. Amandi asked Democratic strategist Mark Riddle, who lives in St. Petersburg, to take lunch with Jolly and hear him out. They talked about housing insurance and affordability, which would become tenets of Jolly’s platform.
After that meeting, Riddle checked out one of Jolly’s town hall meetings in Sarasota.
“This wasn’t 30 or 40 people showing up,” Riddle said. “This was 400 to 500 people showing up.”
Before making the run official, Riddle told Jolly he needed to meet with Sink.
“Alex is one of the first calls you make if you’re a Democrat running a statewide campaign,” Riddle said. “She has tentacles that run throughout the state. I thought it was important that they meet so he gets that validation. It was a critical moment.”
Learning curve
As Sink listened to Jolly in Panera, she thought he sounded smart and as eloquent as he was on MSNBC.
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But she had notes.
Jolly obviously needed to register as a Democrat and get in the race before anyone else.
“If he was serious about what he was doing, he needed to introduce himself early and prove himself,” Sink said.
That meant talking convincingly on issues that were problematic for him. The main one: abortion, which he had opposed when he was in Congress. Sink urged him to speak to policy experts and be transparent about how his ideas evolved.
Sink had another concern. Jolly needed to convince Democrats that they weren’t in for a repeat of 2014 and 2022, when another former Republican from Pinellas ran for governor and lost.
“Democrats are going to say that you’re just Charlie Crist warmed over,” Sink said she told him.
The learning curve was steep. Jolly had virtually no contacts in the Florida Democratic Party.
On the road
Jolly registered as a Democrat in April and filed to run in June. With his ties to MS NOW (formerly MSNBC), he figured he could shake loose $20 million or so.
“Our small donors were OK, but big donors?” Jolly said. “Nobody would take my call.”
So Jolly barnstormed the state. In less than a year, Jolly and his team held more than 300 town halls, often visiting counties that were overwhelmingly Republican.
“We hit the road,” Riddle said. “It was David’s idea. Let’s go to places where Democrats don’t usually go. Let’s go north, south, anywhere we could talk to voters, and not just show up once, but go back, over and over.”
Panhandle residents couldn’t believe that a Democrat was spending so much time in their deep-red part of the state.
“David came to Pensacola multiple times without fanfare or media attention,” said Lumon May, an Escambia County commissioner. “This was the first time I saw a Democratic or a Republican candidate for governor open an office in northwest Florida.”
It wasn’t until Halloween that another prominent Democrat, Orange County Mayor Jerry Demings, filed to run against Jolly.
“We stepped on the gas pedal,” Riddle recalled.
In it to win it
Demings said Jolly’s early start didn’t scare him. He said he got into the race knowing he could beat Jolly.
“I’m not a talking head,” Demings told the Times. “I’m someone who got stuff done.”
Demings was a fearsome opponent to face in the Democratic primary.
Orlando’s first Black police chief in 1998. The first Black Orange County sheriff a decade later. Finally, the county’s first Black mayor in 2018 overseeing a $7 billion budget and 8,000 employees.
His wife, former U.S. Rep. Val Demings, made the couple a dynasty. She gained national attention for serving as a House impeachment manager in the first Senate trial of Trump in 2020. Afterward, she was considered a possible running mate for Joe Biden until he chose Kamala Harris. She skipped reelection to run for the U.S. Senate, which she lost to Marco Rubio in 2022.
But Jerry Demings had the same problem Jolly did. There was no money.
He said donors told him they couldn’t give and risk retribution if they bet on the wrong candidate.
Though polls showed a close race weeks after Demings got in, Jolly by February had widened his lead to 8 percentage points, which only grew in the coming weeks.
“He was a full-time mayor of Orange County, and he didn’t have time to hit the road like I did,” Jolly said. “And we had already locked up much of the state.”
Demings, though, said much of the state was still in play and that he was traveling quite a bit. But he withdrew from the race in June after he was diagnosed with prostate cancer.
Though he said he still thinks he could have won the primary, Demings gave credit to Jolly’s campaign.
“He had the courage to get in early,” Demings said. “He campaigned as well as any Democrat in Florida.”
Five days after Demings dropped out, Jolly named former U.S. Rep. Gwen Graham, the daughter of former Democratic Gov. Bob Graham, as his running mate.
Jolly continued touring, winning over Democrats with his energy.
“One of the reasons I’m a proud Florida Democrat is because there’s a fundamental truth we all believe in: that absolutely everybody’s rights should be protected and their dignity celebrated, regardless of the color of your skin, where you are born, who you are, or who you worship,” Jolly told Hillsborough County Democrats with an almost religious fervor close to the primary. “Culture wars have victims.”
Competing in November’s general election will be different. Registered Republicans far outnumber registered Democrats in Florida, and the winner of the GOP primary, U.S. Rep. Byron Donalds, has raised more than 11 times what Jolly has in the race to succeed Gov. Ron DeSantis.
Still, Democrats say they have reason to be optimistic.
“This is the best chance to win that Democrats have had in a long time,” Sink said.
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©2026 Tampa Bay Times. Visit tampabay.com. Distributed by Tribune Content Agency, LLC.
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