Jacksonville Mayor Donna Deegan shocked, for whatever reason, various local Republicans with her endorsement of Kamala Harris for president. 

Deegan has always had a good dynamic with Harris and in fact is the second Jacksonville mayor to meet with her as VP; recall that Lenny Curry and Harris confabbed during the pandemic, as our COVID response was spotlighted. (That all seems like a fever dream now.)

Deegan is a capital-L Liberal Democrat. People were shocked she was with Andrew Gillum early in the 2018 gubernatorial election cycle. But he was the only candidate in the primary race talking about real equity issues. The other Dems came from institutional wealth, and the GOP race was about … other things altogether. 

So no reason to be shocked by her endorsement of Harris.

But does Jacksonville benefit more from Harris or Trump?

Consider this: Deegan has had a strong relationship to the Biden administration, and that will continue if Harris is elected. And the city will need it; recall that soon-to-be state Sen. Randy Fine vowed to keep Jacksonville from getting state funding for projects, though Gov. Ron DeSantis has done a good job of that already in his own right.

Without federal largesse, we won’t have small-gesse or any gesse at all.

And this is a city with problems. We’ve spent up to the cap, with capital obligations. With a mayor who has dropped the shade on the promised transparency window gradually over her time in office, and who has been late and reactive on questions ranging from her London travel costs to stadium spending to a pension deal for cops who shivved her for not going to an officer’s funeral last month, with a city council eager to force her into a defensive posture every possible news cycle.

Jacksonville, like many cash-strapped big cities whose cool hip enclaves are falling into dissolution and disrepair, needs federal help. And this mayor, who has all the name recognition in the world, needs wins. Because though the city council doesn’t have a breakout figure yet for the 2027 race, there are some candidates … including council member Kevin Carrico, who people in the GOP establishment around a certain previous mayor seem to like.

There will be time to talk about 2027 in the future. For now, it makes sense why Deegan is endorsing Harris. Especially given the hundreds of millions of dollars that has come in from Washington during the Biden-Deegan era. “It’s nearly $800 million counting the $647 million to the city,” said Deegan spox Phil Perry, including “the $147 million for the Emerald Trail. These figures don’t include additional federal grants that JEA, JTA, JAXPORT, etc. have received.”

But the remote endorsement is bittersweet for Democrats, including some of this column’s readers, who thought Harris in Jax would have made an Obama 2008-type play to the two-state local media market. Deegan has not traveled for Harris either, a contrast to the many Dems deployed to swing states.

Still, formalizing the alliance and leaving no doubt may be key to some much needed capital — especially given our real estate bubble is bursting, and we will have millage challenges in a Florida where the rent is too damn high and the ROI is too low. 

Speaking of ROI, another figure with a lot on the line Tuesday is America’s Governor – Ronald Dion DeSantis. 

If Trump and Vance win, DeSantis will never be the Republican nominee for President. Vance’s selection was a direct block of DeSantis by Trump, given that the Hillbilly Elegy author is quicker on his feet, more modulated in his tone, and more comfortable in his own skin than a man so awkward that he spent a year in boots and lifts while running for president and winning no counties while spending $168 million. 

But if Harris wins? DeSantis gets to talk smack for four years, two of them on the taxpayer dime, as a lame duck. A Harris victory comes with a Trump collapse, perhaps one cinched with Harris getting a showcase on Saturday Night Live.

For a vastly different outlet, I argued that this was a “vibes” election early this summer. Is that the case today though? More so than it’s been for weeks. Since the ill-fated Trump rally in New York with the catastrophic roast comic Tony Hinchcliffe cooking Trump with Puerto Rico putdowns under the banner and with the sanction of his campaign, Trump has struggled to stay in a proactive mode. While neither Harris nor VP nominee Tim Walz are especially inspired or extemporaneous speakers compared to Trump, the Don Rickles of politics, it seems like the GOP nominee is on a bad beat at the worst possible time. 

So if Trump loses, DeSantis is there to pick up the pieces — a poor man’s imitation of Richard Nixon after Barry Goldwater’s predictable loss in 1964.

The MAGAs will never love robotic Ron, of course, or trust him after he twisted a knife in Trump’s back. But DeSantis can triangulate enough to potentially ward off an actual populist challenger to his right. The governor, after all, is a corporatist, rather than a moral evangelist. A prosecutor, not a prophet.

With this in mind, some thoughts on the constitutional amendments – specifically Amendment 3 (Adult Personal Use of Marijuana) and Amendment 4, which removes state restrictions on abortion to much farther along in the process of gestation.

The governor has worked very hard to kill both, spending at least $16 million in state agency ad money, along with travel and hard costs, to go hither and yon and evangelize against said citizens’ initiatives at “press conferences” where Ron and the first lady don’t take actual questions.

Someone asked me a good question: What if it’s in DeSantis’ interest to lose?

If the weed amendment (which has been endorsed by Donald Trump) passes, he can recalibrate away from that message to something more libertarian and less authoritarian. And if the experiences of pols in other states who abandon prohibition is any indication, he can make some money along the way with savvy investments in the new industry. 

And if the abortion amendment passes, he doesn’t have to defend an abortion law so far to the right that Trump himself can’t stop trashing it. 

In addition to the $168 million, DeSantis spent more state money and resources than you want to think of on the garish performance art spectacle that was his 2024 campaign, an ensemble cast of grifters and the terminally online who delighted in ‘owning the libs’ and ‘whuppin’ the woke.’ It got him nowhere because no one wants a moralistic scolding from a man in platform shoes.

If there’s a Ron 2.0 or 3.0 or 5.0 or whatever the new model is, he needs to move on from the culture wars and find a Reaganesque optimism that doesn’t come naturally to him, as it clashes with the perpetual drone of grievance.