Trump Keeping Close Eye on DeSantis, Has Reportedly Identified a Key Weakness


While the field is theoretically wide open, the presidential nomination for the GOP in 2024 thus far has seemed like a two-horse race between former President Donald Trump and Florida Gov. Ron DeSantis.

Now, a Washington Post report says Trump’s advisers have identified a key weakness in DeSantis’ chances: While his act may work in Florida, he’s never undertaken a campaign on the national stage and could wither once he’s tested.

“Trump’s advisers said they see weaknesses in DeSantis that could inform their strategy against him, should they be pitted against each other in 2024,” the paper reported Saturday.

“They argue that he’s not tested on a national stage and that he is not a compelling speaker. Some people who have met DeSantis earlier this year described the governor as a poor conversationalist with donors.”

What’s clear is that the two are now de facto competitors. When Trump endorsed DeSantis for governor in 2018, he called the Harvard Law grad and Navy vet a “tough, brilliant cookie” and a “great friend.”

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However, the former president — now officially a Florida resident, it’s worth noting — has yet to endorse DeSantis as he runs for a second term as governor. For his part, DeSantis has not asked Trump to campaign, according to the Post.

A Trump adviser told the Post that although the two had spoken regularly, “those days are gone” and the two top GOP dogs haven’t spoken since early in the summer.

Unnamed sources, according to the Post, said Trump has also called DeSantis ungrateful, telling advisers, “I made him.”

“I knew him from watching Fox, and he’d done a good job about me and other things. He’s an Ivy League baseball player,” Trump said, according to the Post, which cited “a person who has visited his Mar-a-Lago Club and heard him talk about DeSantis.”

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“I don’t understand what happened here,” Trump reportedly said. “I don’t understand why he doesn’t appreciate me more.”

The general consensus, the Post’s Hannah Knowles and Josh Dawsey found, was that the Republican base was enthusiastic about DeSantis’ agenda — particularly his opposition to COVID restrictions and indoctrination in public schools — but that most still leaned toward Trump in 2024.

DeSantis donor Don Tapia, an ambassador to Jamaica under the Trump administration, told the Post that while the Florida governor “is building a base with the Trump people,” the fact remains that “right now the Republican base is Donald Trump’s base.”

However, Trump has the complication of several legal cases or criminal investigations with him at the center of them — politically motivated though they may be — and little social media access aside from his own Truth Social. The Post also reported that “Trump advisers said DeSantis has tapped into the conservative zeitgeist on cultural issues in a way that Trump did in 2016 but has struggled to do since leaving office.”

“In recently flying migrants from Texas to a liberal enclave, Martha’s Vineyard, DeSantis took a polarizing step that Trump considered as president but eventually scuttled,” the Post noted.

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“It drew attention and outrage from Democrats and human rights advocates and delighted the conservative base on an issue core to Trump’s political identity: immigration.”

At least for the moment, DeSantis seems to best fill the role of a candidate who would represent what many have been fond of calling “Trumpism without Trump”: The populist appeal of the former president and ability to successfully fight cultural battles while moving the GOP beyond the empty, libertarian-lite free-market orthodoxy of the early 2010s, but without the baggage and distractions Trump would bring to the table, particularly after the Capitol incursion that Democrats are still flogging as an “insurrection.”

However, the concept of “Trumpism without Trump” is a double-edged sword — because as much as Trump’s personality engenders a love-or-loathe reaction, it’s still a personality that has dominated American politics since Trump declared for the presidency back in 2015.

Even if the former president no longer has access to mainstream social media platforms thanks to a blanket ban, he’s spoken frequently at campaign events for other GOP candidates, racking up coverage that way. If and when his 2024 campaign commences, the stem-winders are going to get longer and more colorful — and the mainstream media can’t help but to lap it all up, even if just to condemn it.

Meanwhile, while I know The New Yorker isn’t known for its political even-handedness, this passage from a June profile of the Florida governor by former New York Times reporter Dexter Filkins might capture a side of DeSantis that isn’t visible when he’s speaking on stage:

  “People who work closely with him describe a man so aloof that he sometimes finds it difficult to carry on a conversation. ‘He’s not comfortable engaging other people,’ a political leader who sees him often told me. ‘He walks into the meeting and doesn’t acknowledge the rest of us. There’s no eye contact and little or no interaction. The moment I start to ask him a question, his head twitches. You can tell he doesn’t want to be there.’

“Nearly everyone I talked to who knew DeSantis commented on his affect: his lack of curiosity about others, his indifferent table manners, his aversion to the political rituals of dispensing handshakes and questions about the kids. One former associate told me that his demeanor stems from a conviction that others have advantages that were denied to him. “’The anger comes more easily to him because he has a chip on his shoulder,’ she said. ‘He is a serious guy. Driven.'”

In a straight-up personality contest with a former president whose speeches often come across as improvisational political comedy, DeSantis is running behind even before the race starts.

Of course, personality isn’t everything. The “who would you rather have a beer with?” test is oft overrated; while both Trump and Biden are teetotalers, I can imagine most of America would rather have a beer with someone who is coherent.

That’s not Joe Biden, yet Biden is the one in the White House — thanks in large part to the massive influence of bias in the mainstream media and Big Tech that marked the 2020 presidential campaign.

Furthermore, we’ve yet to see how a Trump campaign without social media access will play out, or whether DeSantis can convince voters they should have a beer with someone who, while “aloof” and “indifferent,” has racked up an impressive record while the former president has been sidelined.

Nevertheless, don’t forget how easily top Republican contenders on the 2016 campaign trail wilted and died after a particularly mordant remark from Trump. Remember how the pejorative “Little Marco” ended up defining Florida Sen. Marco Rubio for the remainder of the campaign, or how “Low-Energy Jeb” managed to tar one-time 2016 GOP frontrunner Jeb Bush.

There are ways to counter this kind of thing, of course. None of them involve being “aloof” or “indifferent.” Trump is right to be worried about DeSantis, but his team certainly seems to have zeroed in on one of the governor’s major weaknesses. Whether it ends up being a fatal flaw, only time will tell.

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C. Douglas Golden is a writer who splits his time between the United States and Southeast Asia. Specializing in political commentary and world affairs, he's written for Conservative Tribune and The Western Journal since 2014.
C. Douglas Golden is a writer who splits his time between the United States and Southeast Asia. Specializing in political commentary and world affairs, he's written for Conservative Tribune and The Western Journal since 2014. Aside from politics, he enjoys spending time with his wife, literature (especially British comic novels and modern Japanese lit), indie rock, coffee, Formula One and football (of both American and world varieties).
Morristown, New Jersey
Catholic University of America
Languages Spoken
English, Spanish
Topics of Expertise
American Politics, World Politics, Culture