Winner and Loser of the Week in Florida politics — Week of 10.29.23

Ron DeSantis got embarrassed this week by Republicans in his own state, and all the heel lifts in the world may not get him out of this hole.

As Ron DeSantis continues to struggle in the 2024 Primary (more on that later), his camp is moving more aggressively than ever to lampoon former President Donald Trump.

Team DeSantis is incredibly late to the party on this one, having seen his poll numbers fall into the abyss even before launching his bid as he let Trump savage him publicly for months. But while the strategy may be too little, too late, Trump is giving DeSantis’ camp plenty to work with recently.

Trump himself tries to make President Joe Biden out to be a doddering old fool (again, not a difficult task given the President’s age and frequent gaffes). But Trump appears to be slipping up more often as well.

Appearing in Sioux City, Iowa, this week, Trump flubbed the name of the city and called it Sioux Falls. After being corrected by a state lawmaker there, Trump tried to save face by re-approaching the microphone and saying the name correctly.

Speaking in New Hampshire last week, Trump incorrectly identified Hungarian Prime Minister Viktor Orbán as the leader of Turkey. Then early this week in Sioux City, he was able to pinpoint Orbán as the leader of Hungary but improperly stated the country borders Russia.

Trump has also been caught in recent weeks warning about the possibility of World War II (instead of World War III), stating he defeated Barack Obama in 2016, and misidentifying George W. Bush as Jeb Bush.

To Trump supporters: If Biden made those repeated mistakes, you’d be having a field day, no? Well it does appear as if former President Trump (also a very old man!) does appear to be losing the zip on his fastball, as DeSantis put it.

But while Biden’s gaffes have become a relentless source of mockery for Republicans and many voters, Trump hasn’t yet been effectively painted as the aging fountain of errors he appears to now be.

That may change with DeSantis and others pressing this messaging more. But Team Trump needs to be wary of going after Biden so viciously for his mistakes if Trump can’t even pronounce “Hamas.”

Now, it’s on to our weekly game of winners and losers.


Honorable mention: New law enforcement recruits. A DeSantis-backed push to recruit more out-of-state law enforcement officers to Florida appears to be working.

The Governor announced this week that more than 3,350 bonuses have been doled out under the Law Enforcement Recruitment Bonus Program, adding up to more than $22.5 million. Of those who received bonuses, 915 have relocated to Florida from out-of-state. The program has attracted law enforcement officers from all 50 states and two U.S. territories, according to the Governor.

“With a national lack of support for the important work law enforcement officers do daily, Florida has stood up for what is right,” DeSantis said.

“We will continue to support law and order and make investments in the people that keep our communities safe.”

The program is targeted at new recruits inside Florida as well as individuals looking to move to Florida from elsewhere to work in law enforcement. Those who utilize the program can earn a bonus of $5,000.

DeSantis has sought to showcase himself as a law-and-order Governor, and it appears that messaging is resonating within the law enforcement community.

Almost (but not quite) the biggest winner: Vern Buchanan. This week it was announced that Buchanan would host the first major fundraiser for new Speaker Mike Johnson of Louisiana, a significant get for Buchanan as he attempts to build ties to the new GOP conference leader.

The bad blood between Buchanan and now-former Speaker Kevin McCarthy is well-documented.

After McCarthy barely secured the gavel in January, Buchanan thought he’d be in line for Ways & Means Chair, and with good reason. Buchanan was the party’s best fundraiser outside of leadership, and he and McCarthy entered Congress in the same class.

But when was passed over for the gavel in favor of U.S. Rep. Jason Smith of Missouri, he reportedly cursed out McCarthy, accusing the then-Speaker of whipping votes against him.

Well, with McCarthy out, Buchanan is attempting to avoid a repeat by building strong ties with Johnson. The fundraiser will take place on Nov. 27, where the Longboat Key Republican will show Republicans once again that he’s one of the best fundraisers in the party. Maybe they could return the favor by not screwing him over next time a coveted Chair position comes open.

The biggest winner: Gamblers. We told you last week to get your bankroll ready after the U.S. Supreme Court cleared aside a federal challenge to the Gaming Compact between the Seminole Tribe of Florida and the state that would open the door to craps, roulette and sports betting. Well, that time is coming sooner than we thought.

The Seminole Tribe of Florida announced this week a Dec. 7 launch date for those games at the Tribe’s South Florida outfits: Seminole Hard Rock Hotel & Casino Hollywood, Seminole Classic Casino in Hollywood and Seminole Casino Coconut Creek.

The new games will come to Seminole Hard Rock Hotel & Casino Tampa on Dec. 8 and will arrive at Seminole Casino Immokalee and Seminole Brighton Casino on Dec. 11.

Yes, there is still a challenge to the Gaming Compact in state court pending. So far, that is keeping in limbo an expansion of the mobile betting app that would allow sports fans to wager on games from their own home. But the Seminole Tribe of Florida is plowing forward on the other expanded offerings allowed under the Compact.

Next month’s launch will feature “star-studded” events to help bring attention to the new gaming opportunities. But something tells me this is going to be a boon to their properties — and the state of Florida — with or without the flashy promotion.


Dishonorable mention: Keith Gross. Look, it’s unlikely any Republican is seizing the GOP nomination from U.S. Sen. Rick Scott as Scott runs for re-election. But Gross is making it far too easy given his background, per a report this week.

Matt Dixon of NBC News reported that Gross was previously kicked off the ballot due to concerns he lied about being eligible to run for a Georgia legislative seat as a Democrat.

If you’re keeping score at home, those are allegations that Gross is:

— A former Democrat.

— A carpetbagger.

— Someone who was accused of fraudulently running for office by lying about meeting the state’s residency requirements (accusations which a judge agreed with).

Gross has said he’s willing to put up big cash to challenge Scott — up to $30 million. Throwing that much cash at a race is what propelled Scott into the Governor’s Mansion in 2010, when he defeated party favorite Bill McCollum in the Primary.

But McCollum, then the Attorney General, was not the incumbent Governor. Scott has been serving in prominent roles in Florida government for more than a decade now. And while his record is not above criticism, it’s hard to argue that a guy with Gross’ background is the one to unseat a sitting Senator.

Almost (but not quite) the biggest loser: DeSantis’ Disney district. DeSantis may be doing a bang-up job accomplishing his goal of recruiting law enforcement officers to Florida. But another major focus of his tenure, his ill-advised war against one of Florida’s largest economic engines, continues to look more foolish by the day.

This week saw reports that more than 30 employees have quit the district amid concerns that new leaders of the Central Florida Tourism Oversight District (CFTOD) are, according to one now-departed employee, “unqualified and incompetent.”

Having long-standing employees working behind the scenes to make the massive region home to Disney’s theme parks click is bad enough. But this week also saw district leaders reveal they had canceled a controversial no-bid contract connected to the area’s 911 network.

According to Shannon Butler of WFTV, the DeSantis-installed district board awarded a $242,500 contract to Figgers Communication without accepting other bids.

Who runs Figgers Communication? Well that happens to be Freddie Figgers, who DeSantis appointed to the Florida Commission on Ethics. Figgers, by the way, served on that body with now-CFTOD District Administrator Glen Gilzean.

Facing questions surrounding the process, that contract will now go up for a bid — which should have happened in the first place.

Maybe if they didn’t have employees abandoning ship left and right, the board members could have gotten some guidance on how to run this search correctly from the start.

The biggest loser: DeSantis. Alright, where to begin?

We dubbed DeSantis a loser last week after state Rep. Randy Fine flipped his endorsement from DeSantis to Trump and former DeSantis backer Ken Griffin spoke effusively about 2024 rival Nikki Haley as the GOP world continues weighing Haley as the potential non-Trump option in the Republican field.

We noted, however, that DeSantis could rebound with a strong showing in the Des Moines Register poll of the Iowa GOP Primary, released Monday.

Instead, DeSantis was tied with Haley for second. Plenty of voters are still weighing DeSantis as an option, according to the poll. But the topline numbers show DeSantis now even with Haley and still 27 points behind Trump.

That’s in addition to Haley now doubling up DeSantis’ support in South Carolina and moving into second in New Hampshire, with Haley seemingly nearing an endorsement from that state’s Governor, Chris Sununu.

Polling woes are nothing new for the Governor, however (though these are particularly pronounced). This week, though, may stand out as the most embarrassing yet during DeSantis’ 2024 run.

Exhibit A: Bootgate. It’s a jab at the Governor that’s been floating around for months now. Is he insecure about his height and wearing lifts in his boots to compensate? That was the question posed on social media to jab at DeSantis, but it hadn’t really blown up as a story.

That is, until DeSantis for some reason went on the PBD Podcast, an outlet no presidential candidate would have ever even entertained visiting in cycles past. There, DeSantis faced questions about the memes regarding his boost. DeSantis gave an awkward answer, and we were off to the races.

The talk resulted in a POLITICO piece where three “expert shoemakers” argued he is wearing boosters. And later in the week, DeSantis was still giving this airtime during a Newsmax hit. Yes, he was pushing back on the story, but giving it oxygen at all only made his critics cackle even louder. The loudest among them are members of Team Trump, but even Haley got in on the action.

And then there’s the Florida Freedom Summit, an event where DeSantis should have been the superstar after rocketing to national notoriety given his leadership of the state.

Instead, DeSantis was relegated to a 1:30 p.m. speaking spot. U.S. Sen. Tim Scott and Vivek Ramaswamy got later speaking slots than Florida’s Governor. State Rep. Fine nabbed a spot right after DeSantis on a panel regarding the situation in Israel. And Trump was pegged as the event’s keynote speaker.

Days before the event, U.S. Sen. Rick Scott endorsed Trump over DeSantis, a move away from previous statements that he wouldn’t pick sides in the GOP Primary. And the Freedom Summit featured several state lawmakers joining Fine in swapping their support from DeSantis and Trump.

It is hard to overstate what a fall from grace this Governor has had, from serving as the next conservative superstar to seeing lawmakers in his own state abandon ship and the state’s Republican Party shaft him at its signature event of the year.

If members of the GOP from DeSantis’ own home don’t have faith in his bid, why should the rest of the country?

Ryan Nicol

Ryan Nicol covers news out of South Florida for Florida Politics. Ryan is a native Floridian who attended undergrad at Nova Southeastern University before moving on to law school at Florida State. After graduating with a law degree he moved into the news industry, working in TV News as a writer and producer, along with some freelance writing work. If you'd like to contact him, send an email to [email protected].


  • PeterH

    November 5, 2023 at 5:55 am

    Good article! I must make a note to self. The difference between Biden and his apparent 2024 presidential contender Donald Trump, is the fact that Joe Biden has surrounded his administration with highly qualified advisers who manage the day to day challenges of government. Donald Trump on the other hand wanders the political landscape thinking only he has the knowledge and ability to make decisions.

  • S. "Tory" Tellun

    November 5, 2023 at 8:16 am

    It was some time ago that Paul Krugman, one of the most leftish of Manhattan commenters, complained of conservative columnists that they wouldn’t pull their feet out of the snark and stick to issues. I wonder what he would say about FLA POL, which has given up on real reporting and descended into a cesspool of sarcasm, so emblematic of St. Petersburg storytelling.

  • Michael K

    November 5, 2023 at 9:47 am

    More sunshine, please! The Disney oversight board mess demonstrates how cronyism, corruption, and complete disregard for the state procurement process are exposing DeSantis’ hubris and vengeance.

    I can only hope that state Republicans are learning their lesson and will stop kowtowing to a failing governor. Meanwhile, the destruction of our public education system has become a toxic stain on Florida that will take years to correct.

Comments are closed.


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