Jacksonville Mayor Donna Deegan speaks to a crowd at the Legends Center in Northwest Jacksonville | Casmira Harrison, Jacksonville Today
Published on March 16, 2025 at 9:00 am
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Sometimes I wonder if I’m on the wrong side of the business.
Political commentary has paid most of the bills over the years, but the real money is in consulting.
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And the real money locally – at least in theory – is coming up in the 2027 race for Jacksonville mayor.
Lots of Republicans could be factors, and some are even showing a little leg.
State Rep. Wyman Duggan is term-limited next year, which gives him a logical runway between the 2026 legislative session’s sine die and the March 2027 first municipal election. He’s one of the smartest policy minds in the region and he’s mattered in the House most of his tenure.
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If you drank everytime City Councilman Rory Diamond tweeted “We need a new mayor,” you’d have cirrhosis of the liver. Diamond has made no secret of his desire to continue in politics; he’s term-limited in 2027.
And of course, there’s the Duke of DOGE himself, City Council Finance Chair Ron Salem.
Salem seems to have floated a trial balloon, based on what sources familiar are floating, in the so-called invisible primary. The case he seems to want to make is that the big-ticket budgets and spending he’s voted for every chance he’s gotten the last five years may have gone a bridge too far.
Former Mayor Lenny Curry is not exactly on board with this.
“Your source is talking to a consultant to a career politician or direct to a career politician. This is a bologna sandwich from a political hack amateur that doesn’t know how to win the big game. And this person or their consultant still thinks this individual can be Mayor someday. Laughable,” Curry posted to X.
Meanwhile, there’s incoming City Council President Kevin Carrico, who apparently will look to sideline Salem and other old heads by elevating younger council members to committee head positions. That’s a good way to broker future endorsements, should he want to run.
There’s a problem here, though, and it’s a numbers game.
A group of candidates would necessarily be compelled to frag each other, just as Republicans did in 2023, when the only bad blood of the entire campaign was between the Daniel Davis side and the Al Ferraro and Leanna Cumber camps, while Donna Deegan was able to shrug off anything fellow Democrat Audrey Gibson had to say.
And after it all wrapped up, Davis and Deegan have played in the same sandbox just fine, with that fat Jax Chamber paycheck Davis earns as CEO serving as balm for any post-campaign bruises the 2023 runner-up may have felt.
And just as in 2023, Republicans would be fighting over the donor pie – and it remains to be seen how many slices there will be, given the bad bet made on Davis two years ago.
Deegan wasn’t beatable as a non-incumbent. How do they beat her now that she’s in office?
There is a path, of course. But whether they have the political discipline and the ability to consolidate big money support before things get serious next year is a much more open question.
Because if qualifying week comes around and it’s Donna and the Seven Dwarfs, it’s pretty easy to see how that movie ends.
A smart candidate would look to close the field by creating some strategic alliances, for one thing. Chief of staff, chief administrative officer, and the other big-dollar positions are incredibly smart bargaining chips. If Mayor Alvin Brown, a Democrat, had won re-election in 2015, the buzz was that Republican Bill Bishop would have gotten a key job in his second-term office – and if Bishop’s endorsement actually had legs, it would have been a worthwhile barter.
A smart candidate would have already started putting their political committees to work. Push polls to test messages. Texts and even mail to hit the mayor where she is vulnerable, using blinder committees to hide the source. Florida’s exceedingly forgiving campaign finance laws are excellent news for those who want to obscure where a nasty piece of business is coming from.
Defeating a popular mayor requires playing the margins and angles, and it doesn’t seem anyone currently in the mix understands that.
The best example of that gamesmanship was way back in 2015, when Lenny Curry, Brian Hughes, and Tim Baker found ways to chip away at Brown’s image and defeat the Democrat in May even though their own internal polling said the incumbent had a 55% approval rating.
Deegan presents challenges that Brown didn’t, of course. For one thing, she’s much better at trash talking than any of her opponents. For another thing, her administration’s branding efforts are light years ahead of Brown’s.
Anyone out of the group who wants to win in 2027 will need to start by winning in 2025 and 2026.
