How Tom Keen won HD 35 and why it’s all Ron DeSantis’ fault

Tom Keen. Ron DeSantis

A Special Election in Central Florida kept consultants in both parties chewing fingernails until officials tabulated the final votes. So how did underdog Tom Keen pull off the win in House District 35?

Democrats credit a solid ground game by state Rep.-elect Tom Keen, who defeated Republican Erika Booth by about 600 votes. But professionals on both sides of the aisle also point at another looming figure, Gov. Ron DeSantis, who offered little assistance to Republicans after effectively setting a Special Election into motion.

Voters in the district elected a Republican by a landslide in November 2022, the only other election since redistricting established new boundaries. But just 14 months after that vote, Democrats won on the same turf, with voters delivering a 12-point net swing from the last time they chose a Representative.

As with any election, experts point to a multitude of factors that can decide any race, especially a low-turnout Special Election. But watching a flood of Florida Republicans flock to Iowa’s Winter instead of Christmas, Florida, left many questioning if the Governor’s floundering Presidential Election bid has the potential to hurt his party down ballot even when he’s not running here, or even because he is running everywhere else.

Considering DeSantis didn’t win a single county in the Iowa caucuses, the HD 35 loss seemed a political insult atop an electoral injury for a one-time political giant whose stature has weakened in Florida as his standing diminishes nationwide.

Brushing a win aside

Since Florida’s last General Election, the House experienced three Special Elections to fill vacancies. This proved to be the first contest Republicans lost, and the only one to date to change the partisan makeup of the chamber.

This was the first such election in a swing district, of course. State Rep. Ryan Chamberlin, a Belleview Republican, didn’t even face a Democrat when he won a House District 24 race last May.

Seven months later, Democrats overperformed in House District 118, holding state Rep. Mike Redondo, a Miami-Dade Republican, to a 6-point win. The outcome in a district DeSantis won by 30 points may never truly have been in doubt, but the race did suggest the DeSantis era of electoral dominance already appeared in jeopardy.

Still, Republicans had reason for optimism in HD 35. While voters there favored Joe Biden in the 2020 Presidential Election by 5 points, Republicans rode DeSantis’ coattails in 2022 to supermajorities in the Legislature, and seemed to gain significant strength in Central Florida.

DeSantis himself had openly wondered at points if the party in 2022 should have pushed harder to defeat Democratic U.S. Rep. Darren Soto or state Sen. Vic Torres, as Osceola County showed a greater Republican tilt.

The party did find success in HD 35, where state Rep. Fred Hawkins, a St. Cloud Republican, clocked Democrat Rishi Bagga in a 10-point landslide. But Hawkins, a close ally of DeSantis who sponsored the legislative overhaul of Disney’s tax district, didn’t serve out his term.

In a move that ultimately set the entire Special Election into motion, calls from the Governor’s Office effectively stopped a search process for a new President at South Florida State College. Three finalists for the job withdrew applications, and a search committee for the college soon announced Hawkins as the lone finalist for the job instead.

The process was closely investigated by The Herald-Advocate; its coverage is no longer available. The reporting was aggregated in detail by the Seeking Rents blog.

That prompted Hawkins to resign his House seat, and the former lawmaker has no regrets, even after seeing his seat flip blue. “I played a role in politics, but from the moment I was in the House, Speaker (Chris) Sprowls and Speaker (Paul) Renner said I’m an education guy and I embraced that,” he said.

“I saw this as an opportunity to continue in that. It’s amazing that in a role like this you launch futures of people you may never meet face-to-face.”

The opening of a Biden district held by Republicans immediately sparked interest on both sides. Ultimately, three Republicans and three Democrats qualified to run for the seat.

Setting the field

State Republicans notably picked a favorite early, with the Florida House Republican Campaign Committee (FHRCC) endorsing Osceola County School Board member Erika Booth over former congressional candidate Scotty Moore and Realtor Ken Davenport, a former candidate Hawkins beat in a Primary in 2022.

On the Democratic side, Keen faced Rishi Bagga, who had defeated him by just 57 votes in a 2022 Primary in the district before losing to Hawkins, and Marucci Guzmán, a Latino Leadership executive and wife of a former Republican lawmaker.

Both parties saw often contentious Primaries. Allies of Moore attacked Booth, wife to Osceola County Commissioner Ricky Booth, as part of a county establishment there. A controversial consultant set up political committees that started endorsing Booth for policies she did not hold, apparently just so other political committees he controlled could attack those positions. Republicans challenged Davenport’s eligibility to run in court.

Booth ultimately won her race with nearly 50% of the vote, but campaign officials acknowledge the contentious Primary made it difficult to unify voters, particularly in Osceola, where she held the strongest levels of support.

The Democratic battle also turned bitter at points. But as the lowest performing fundraiser, Keen somewhat avoided the fray. He did face some criticism for hiring a former Republican campaign consultant, Zane Matter, who once had a falling out with Guzmán’s husband, former state Rep. Rene Plasencia. But he largely avoided an escalating firefight between Bagga and Guzmán before winning the Democratic nomination with under 36% of the vote.

General malaise

Keen at the time cited a head-low strategy and commitment to field work as the secret to his upset victory in the Primary. Democratic leaders, meanwhile, cheered Keen’s work ethic. House Democratic Leader Fentrice Driskell, who intentionally stayed neutral in the Primary, noted to the media that Keen had knocked on more than 3,000 doors just before the August race personally. Keen would triple that number heading into the Jan. 16 Special Election.

Driskell also praised his résumé. “He’s a veteran who dedicated his life to service. It’s a thread throughout his life,” she said of the aerospace engineer.

After the Primary, rumors spread that Republicans had meddled in the race, trying to make Keen the nominee. But on the heels of the loss, sources close to Booth’s campaign said Keen proved the best choice Democrats could make. The businessman seemed clean to the level of boring, but that left opposition researchers coming up empty.

Instead, Republicans tried to exploit the political climate. President Joe Biden is performing historically poorly in the polls as Republican presidential candidates suck up media oxygen.

The top issue listed on Booth’s campaign website was fighting “Joe Biden’s Woke Agenda,” and she posted regularly about the immigration crisis at the border. As a School Board member and former teacher, she similarly promised to deliver on DeSantis’ education agenda.

But DeSantis offered little presence in the race himself. While trying to become the face of the national fight against Biden, DeSantis sightings in the state of Florida became more rare as he campaigned for votes in Iowa and other early presidential states.

Sabotaged from the start

From the moment DeSantis scheduled a Special Election in HD 35, speculation grew that he cared more about his performance in Iowa than the outcome here at home. Despite knowing before anyone that Hawkins would likely be vacating his seat, he set the date for the Special Election on Jan. 16, a month after the HD 118 Special Election and a date after the Jan. 15 Iowa caucuses.

“DeSantis, by my logic, did not want the risk of a flipped seat undermining his electability argument to caucus voters,” wrote Democratic analyst Matt Isbell in his blog Mapping Florida. “Now, since July, the DeSantis campaign became a nightmare, and heading into Monday’s caucuses the HD35 election was the last of their concerns.”

It wasn’t just DeSantis. Dozens of DeSantis political allies and state lawmakers spent the days ahead of caucuses traveling to Iowa to speak to voters and trek through snow in the Midwest.

At the FHRCC, officials swat down notions that the political arm for House Republicans didn’t provide Booth with enough support. Speaker-designate Daniel Perez, a Miami Republican, campaigned in person in HD 35 into the district. So did many Central Florida lawmakers, including Reps. Doug Bankson, Berny Jacques and Jennifer Canady, who also is in line to lead the House in a few years.

“We had many members and the Speaker-designate on the ground helping and walking,” said Sarah Bascom. “The candidate and the campaign were strong and a Caucus in Iowa did not distract our efforts one bit.”

Yet some of the biggest hitters in Florida politics were posting pictures of Iowa snow leading into the election. That included Speaker Paul Renner and another Speaker-to-be, Rep. Sam Garrison. Multiple Republicans in Iowa pushed back on assertions they should be in Kissimmee.

“We also have a big team walking every day in HD 35,” posted state Rep. Will Robinson, a Republican campaigning in Iowa. “Helps to have 80 plus R House members.”

The campaign signals that the FHRCC provided all the support it ever asked for materially, and that leadership provided the manpower to run a solid race.

It could be that Democrats simply provided more. Regardless, whether Republicans spent their energy in the Hawkeye State or in Orange and Osceola, they ended up helping a losing campaign. DeSantis failed to win a single Iowa County and Booth lost by less than 3 percentage points.

Recovery mode

Florida Democratic Party Chair Nikki Fried at a Wednesday press conference couldn’t help but note this had been a terrible week for DeSantis. “This represents Democrats’ first flip of this year, and the second major loss of the week for Ron DeSantis, showing how far he has actually fallen, both nationally and here in our state,” she said.

Keen credited party efforts and the Florida House Democratic Campaign Committee (FHDCC) for helping his campaign on the ground.

“It was really a very encouraging night last night,” he said. “To see the turnout that we got from Democrats, we’re going to see a really good 2024.”

Debbie Mucarsel-Powell, a leading U.S. Senate Democratic candidate, was among the volunteers knocking doors with Keen over the weekend in the district. She cited a Democratic win in Jacksonville, overperformance in HD 118, and the HD 35 outcome as evidence that Democrats in Florida have returned to glory less than two years after DeSantis’ landslide re-election.

She hopes these results have shown national donors that Florida remains a battleground as she prepares to challenge incumbent GOP U.S. Sen. Rick Scott.

“It’s so exciting to see what we saw last night,” she said Wednesday. “The people of Florida, regardless of political affiliation, Democrats and independent voters tired of extremism coming out of Tallahassee. They are tired of politicians like Rick Scott. They are ready for candidates who will lower their cost of living and protect abortion rights.”

Importantly, Scott endorsed Booth, and appears to have provided more help to the campaign than DeSantis.

Democrats overall signaled they intend to run against the property insurance costs under DeSantis’ watch and for a constitutional amendment likely appearing on the ballot that would reverse a six-week abortion ban the Governor signed.

Republicans acknowledge rising insurance rates in the state cost votes at the ballot box. There were actually about 1,700 more registered Republicans who voted in the Special Election than Democrats. That likely means Democrats won a good share of no-party voters in the district, but it also suggests hundreds of disaffected Republicans not only opted against voting for the GOP nominee but went to polls to support Keen.

Some suggest that, more than anything, Democrats simply dumped more resources into the race. The FHRCC poured $207,000 into the race between the Primary and General Election, and spent hundreds of thousands more leading into the Primary to boost Booth’s name ID in the district. But Democrats spent more, with the FHDCC putting in $541,000 over the same time.

The House Republicans’ strategy irked some. Consultant Matt Hurley, who worked with a campaign and dropped out early, noted the party has also been in disarray, with former Republican Party of Florida Chair Christian Ziegler driven out this month amid a sex scandal. But he said problems started before that.

“This is political malpractice at the highest level,” he posted online. “Christian Ziegler’s biggest sin was putting his greasy fingers into the HD 35 Primary. Acted like a mob boss threatening to go after anyone who ran against Booth. Virtually every single state elected official in Florida was knocking on doors for Ron in Iowa this weekend instead of worried about holding serve in Orlando. This is the single biggest political fumble of the year.”

The local GOP downplays that, saying Ziegler didn’t control FHRCC spending, and noting the money spent by House Republicans was massive for a Special Election.

Hawkins said the difference in his last race and the one this week was simply what Democrats were willing to do. “The massive amount of money spent was even shocking to me,” he said. “The Democrats never threw the amount of money at me that they did for this election. I think they saw a chance with just one election going on to raise money and dedicate it to this.”

What now?

That does raise questions about the future. Keen won this race, but by less than 3 points. That’s below Biden’s margin in the district in 2020. He will run again in November as an incumbent, but one who entered office halfway through the Legislative Session and has little opportunity for major accomplishments. And next time, he will run amid Presidential Election year turnout, sharing the ballot with a President trailing in the polls.

“We absolutely believe and plan to win in November,” Bascom said of Republicans. “The fact is we ate into the margin Biden won it by and we will continue that progress throughout this year to get us across the finish line in November.”

Fried, though, feels confident the party now has a blueprint for victory in swing districts. She said Democrats will hold HD 35 and erase Republicans’ supermajority as voters grow increasingly fed up with DeSantis’ agenda and culture wars.

“We are competing everywhere,” she said. “My goal is to fill seats up and down the state. We have a very aggressive campaign strategy, recruiting of candidates all the way from the bottom of the ticket all the way to the top.”

But she also said the only thing that could hurt Republicans more than DeSantis abandoning them to run for President could be him returning to Florida now that country has seen his extremist agenda more vividly and the way the nation has rejected it.

“He hasn’t been here in the state dealing with anything since, virtually, he got sworn in,” Fried said.

“He first had his book tour across the country. He then had his international trade mission and then he went on, then he announced and the entire time he has left our state. You’ve heard and you all know about our property insurance crisis that isn’t being resolved. We have the highest inflation in the nation, almost three times higher than the national average. We have some of the most expensive cities in the country.

“Here in the state of Florida, the fact is voters have gotten to know him and they don’t like him as a person. There is no pathway forward for him.”