TALLAHASSEE — A rematch is underwayin Hillsborough, months after a Democratic newcomer upset a long-time, well-funded Republican.

In March, Democrat Brian Nathan, a first-time candidate, narrowly edged out then-state Rep. Josie Tomkow — an eight-year GOP lawmaker — in a special election for Florida’s 14th Senate District.

Spanning West Tampa, Town ‘N Country and Carrollwood, the area backed President Donald Trump by 7 percentage points in 2024, and leaned even redder by voter registration. But in a low-turnout March special election, triggered when aRepublican incumbent was elevated to lieutenant governor, Nathan won by half apercentage point.

The win was a shock. Tomkow had outspent Nathan 10-to-1 with the full force of Florida’s powerful GOP machine behind her.

It wasn’t enough.

Nathan, a 46-year-old Navy veteran and union leader, thinks he can do it again — even though the stage is larger, the attention more acute, and the GOPis ramping up its efforts to get Tomkow elected.

“Hell yeah I’m confident we will win again!” Nathan said, noting that his campaign strategy in round 2 will be the same: knocking on doors and making phone calls.

“If the Republicans haven’t been able to get it done in the past 27 years, why would they get it done in the next four?” he continued, highlighting a plan to regulate the insurance industry and raise teacher pay. “If my opponent didn’t get it done in 8 years in the House, why would she get it done in the Senate?”

Tomkow, meanwhile, said she’s “working even harder” than she did in March.

“It’s through conversations (with voters) that I feel confident,” she said, adding that her campaign has knockedon “tens of thousands” of doors in the past few months.

“You need someone in the Senate who knows that every issue is a big issue and I’ll be relentless in fighting for my neighbors,” Tomkow said.

Despite being the incumbent, Nathan faces an uphill financial battle — one similar to the dilemma he faced in the special election, but with the added challenge of a more tuned-in audience for the general election.

Across three political committees, Tomkow has nine times more money to spend —over $1.8 million in cash on hand compared to Nathan’s $195,000.

Tomkow, a 30-year-old cattle rancher, has powerful GOP allies. During her eight years in the House, she enjoyed a close relationship with former House Speaker Danny Perez, now the ambassador toBrazil.

Her husband is GOP consultant Tom Piccolo, whose brother served under Gov. Ron DeSantis and whose father is on the board of trustees at the University of South Florida.

Florida Senate District 14 takes up a swath of Hillsborough County. After redistricting in 2022, Jay Collins flipped the seat red by 10 points.

DeSantislast summer picked Collins as his lieutenant governor, leaving the Senate seat open. State rules require the governor to call a special election if a legislative seat is vacated, minimizing how long a district goes unrepresented before the regular elections.

Republicans have long dominated statewide politics. They hold a supermajority in both state legislative chambers and have controlled the Governor’s Mansion for more than two decades as GOP voter registration has exploded compared to Democrats’.

But special election results this year across the country — including Florida Democratic wins by Nathan and Emily Gregory, who flipped a state House seat in Palm Beach County that includes Mar-a-Lago — gave Democrats hope that a bluer midterm was possible.

Nathan was elected after the end of the Legislature’s regular session, butwas involved in three special sessions, which included votes on an AI bill of rights (he voted yes), the proposed property tax amendment (no), and redistricting the state’s congressional seats (no).

The general election is Nov. 3.