Congress has seen plenty of firebrands and confrontational lawmakers — especially from Florida. But Washington still might be in for a shock when it comes to Randy Fine.
Over his nine years in the Florida Legislature, he gained a reputation for his bare-knuckle style of politics and spats with local officials. Now the former gambling executive will be going national with last week’s special election win in a deep-red district on Florida’s northeast coast.
Three years ago, Fine called a school-board member a “whore” in a text. During Covid, he got sanctioned by Facebook after he wrote a post alerting constituents to a school-board meeting on masking that included the school-board member’s phone number. A judge sent Fine to anger management after pictures surfaced that appeared to show him giving the middle finger during a virtual hearing. (He insisted he was scratching his forehead.)
He recently became irritated with a pro-Palestinian activist who was testifying at a hearing and dismissed the man with, “Enjoy your terrorist rag.” When people began to protest, he threatened to empty the room.
“I’m the chairman, I can say what I want,” he said. “If you don’t like it, you can leave.”
And most eye-popping of all, he’s been a frequent foil of Gov. Ron DeSantis ever since he swapped his 2024 presidential endorsement from the governor to Donald Trump, even topping it with a scathing Washington Times op-ed that accused the governor of not doing enough to fight antisemitism in Florida in the wake of the Israel-Hamas war.
Though it’s been more than a year since that fallout, DeSantis has made it clear all is not forgiven. “He repels people,” DeSantis said about Fine in the middle of a 10-minute rant after the election. He then dumped on Fine as someone who had underperformed in the race and argued he was only able to pull off a 14-point victory after the president helped “bail him out in the end.”
Fine’s response: To needle DeSantis over how he has less than two years left in office, with no clear path for where his political career is headed next. “A dying star burns hottest before it fades into oblivion,” Fine wrote on X before taking that same message into his first national interview with FOX Business Network’s “Mornings with Maria.”
Fine has some enemies. But to his allies, his personal style makes him a good lawmaker. “The guy is destined for stardom,” said Florida state Sen. Joe Gruters, another GOP DeSantis antagonist who was Fine’s roommate when they served in the Legislature and is his closest friend. He praised Fine’s “ability to throw the hardest right hook in the business.”
“Somebody punches him, he throws the biggest haymaker that’s around at his opponents,” Gruters said, “and that goes for Republicans and Democrats.”
The ordeal between DeSantis and Fine has been a dramatic U-turn. Fine was once DeSantis’ Jewish outreach chair. He even introduced or co-sponsored many of the policies DeSantis became known for nationally, including measures to limit race-related trainings in classrooms and to punish businesses that allow minors into “adult live performances” — seen by many as targeting drag shows. He was also a key player in the law to give parents more say about what happens in schools, the bill critics like Walt Disney World dubbed the “Don’t Say Gay” law.
And when Disney protested, Fine introduced legislation that aimed to dissolve the theme park’s special tax district. He rejoiced after the feud ended, saying he couldn’t wait to once again enjoy Disney’s cruises and parks with his family.
Chris Sprowls, the former speaker of the Florida House, said he often turned to Fine to ask him to do “really difficult things,” in part because he thought he was smart and could articulate the policy in ways people could easily understand, but also because he could get up and debate against anyone.
“He’s the guy who wants the ball,” Sprowls said. “Every coach wants the guy who wants the ball, and Randy wants the ball for people all the time.”
Gruters agreed. “If you want a bill to pass in the Legislature, the first guy I always recommend is Randy Fine, because he will beat the crap out of his colleagues to try to make sure that that bill passes,” he said. “There’s nobody with the personality and the willingness to get in the mud and make things happen like Randy Fine.”
Nicknamed the “Hebrew Hammer” by Gruters — a title he embraces — Fine was the only Jewish Republican for most of his time in state government.
He has said a key reason he’s in politics is to support pro-Israel causes. But he has also lashed out against Muslims, referring to Josh Weil, his Democratic opponent in the special election who is a convert to Islam, as “Jihad Josh.”
The Florida chapter of the Council on American-Islamic Relations has called for Fine to be censured, including for comments he made on social media saying, “Gaza must be destroyed.” Fine also posted on X that Democratic Reps. Rashida Tlaib of Michigan and Ilhan Omar of Minnesota “might consider leaving before I get there. #BombsAway.”
But the Republican Jewish Coalition endorsed Fine early in his campaign, and his allies defend him as someone passionate about pro-Israel causes and fighting antisemitism.
“He is unapologetic about fighting for Israel,” said Sprowls, who joined Trump and Fine on a trade mission to Israel. He pointed to Hamas’ acts of terrorism and said of Fine: “He’s not going to equivocate on these issues. He’s going to be strong, and I think that is really important to have members like Randy who can fight for the moral imperative that is protecting Israel and their right to live and thrive in the Middle East.”
Trump endorsed Fine over Truth Social before he got into the race and later called him a “tremendous Voice for MAGA.” The race ended up tighter than expected in the closing weeks, with Fine’s opponent polling close to him and estimating he raised $14 million.
Fine was thought to be a shoo-in for the seat previously held by Trump’s national security adviser, Mike Waltz, who has been in hot water recently over accidentally adding The Atlantic’s editor in chief to a messaging group with other top officials. (In an ironic twist, the seat is also the one DeSantis held when he was in Congress.)
Fine said in an interview that he had been interested in going to Congress “when I was a kid.” But when he worked for a congressman one summer, the representative told him, “Don’t do this job until you know how you’ll pay your mortgage. Don’t be like me.” So Fine became a gambling executive whose millions allowed him to mostly retire by age 40. (His state financial disclosure counts his net worth at just over $30 million.)
He didn’t think politics was in his future at that point, but then, he said, “I got mad about my kid’s school.” His son was in first grade and he told the school he didn’t like how they were teaching common core math.
“I got told I wasn’t qualified to have an opinion about it, because I don’t have a degree in academic administration. And look, my degrees from Harvard aren’t worth that much, but I ought to be able to handle first-grade math,” he said, referring to his undergraduate and business graduate degrees from the storied Ivy League school. “We got upset, and so I decided I would go and fix it. And I did: We got out of common core math then I helped pass a law that said you can’t tell a parent they’re not qualified to have an opinion about their kids’ education.”
In January, the Legislature had its first big standoff with DeSantis over illegal immigration, after years of complying to his demands. After a state Senate floor session, many Republicans in the Legislature scattered to avoid talking to any reporters about the tension with the governor. But Fine came out of the chamber ready to discuss what had just gone down and why the Legislature disagreed with the governor’s proposals.
Looking toward the group of journalists, a senior Democratic aide who has described Fine as a “mean-spirited asshole” leaned over to a reporter and whispered, “I disagree with him on almost every issue, but he is very good at what he does.”
Most Democrats in Florida agree with DeSantis on Fine, with state Democratic Party Chair Nikki Fried calling him an “asshole” as well as a “bad politician and a bad person.”
“For the first time in almost six years,” she said, “I agree with Ron DeSantis.”
Jennifer Jenkins, the former school-board member Fine insulted, called him a “piece of shit” and a “bully.” The two have fought over mask mandates and LGBTQ+ policies in schools. Fine also raged at a city councilmember in a text over the fact that county police had invited Jenkins and not him to an event, saying it would jeopardize funding for the Special Olympics and the county, texts obtained by Florida Today showed.
“Randy Fine’s behavior speaks for itself,” Jenkins said. “He is divisive, disrespectful, and entirely untrustworthy. He’s not a leader, he’s a cautionary tale that Florida is about to serve up to the rest of the country on what happens when you let a clown hold office.”
When asked about what his style in Congress would be, Fine said it took him a couple of years to break out in the Legislature. In Congress, he said, it’ll be similar because he’ll be so new and will still have to learn the process and learn from others.
Pressed about it, he said: “I do think that my style will work well in Washington. I mean, I’m an aggressive guy.”