Republican state Rep. Josie Tomkow is trying to advance to the Florida Senate. (Photo via Florida House)
Special legislative elections are taking place Tuesday in three Florida districts previously held by Republicans.
In the Palm Beach County House District 87 race that encompasses Mar-a-Lago (and where Donald Trump voted by mail, even though he calls it “cheating”), Democratic candidate and small business owner Emily Gregory faces Republican financial adviser Jon Maples. It’s a seat formerly held by Rep. Mike Caruso, who was one of Ron DeSantis’ closest allies in the House before he appointed Caruso clerk of the county court last summer.
This seat (as well as the Senate District 14 race) are classic examples of how much the state has shifted from a swing state to a deep red one over the past six years.
Trump won the district by 10 points in 2024 and DeSantis won it by 16 points in 2022.
Caruso won the seat by 19 points in 2024 and 18 points in 2022, but former Democratic Rep. David Silvers won it by more than 25 points in 2020.
Republicans enjoy a 13-point voter registration lead in the district. Yet some observers think Gregory has a shot to pull off the upset.
In the Senate District 14 seat encompassing the western part of Hillsborough County, Republican Rep. Josie Tomkow, term-limited from her House District 51 seat in November, is taking on Democratic union leader Brian Nathan. The seat was held by Republican Jay Collins until he was selected by DeSantis to succeed Jeanette Nuñez as lieutenant governor last summer. Nathan had made an issue about whether Tomkow lives in Polk County, since her husband lives in South Tampa and she has told the Tampa Bay Times that she will move to the district after the election “regardless of whether she wins her race.”
The change in the state party’s demographics over the past several years are also glaring in this former swing district. In 2018, Democrat Janet Cruz defeated Republican Dana Young in a race so close that it went to a recount. Flash forward to 2022, and Cruz lost to Collins by 10 points in a in a race that was expected to be closer. The GOP has a 7-point advantage in the district.
Tomkow has had a huge fundraising advantage lead over Nathan, with a political action committee worth more than $3 million aiding her effort.
Both the HD 87 and SD 14 seats have not had representation in Tallahassee since August.
The third race Tuesday is in House District 51 in Northern Polk County, left vacant because Tomkow left the seat to run for Senate. That’s where Republican Hilary Holley, executive director of an agriculture nonprofit organization, faces Democrat Edwin Edwin Pérez.
This has always been a red-leaning county. Trump won the district by more than 13 points in 2024.
Special thanks to Matt Isbell with MCIMaps.com for his information on voter registration numbers in this story.