Trump's terrible week, explained
His endorsements flopped, Republicans turned on him, and DeSantis emerged as a serious rival. Tired of winning yet?
Just a few days ago, Donald Trump was the undisputed frontrunner for the 2024 Republican presidential nomination. What a difference a dud of a midterm cycle can make.
Trump views himself as a kingmaker of sorts, but his endorsements didn’t amount to much Tuesday. He threw his support behind obviously flawed candidates like Mehmet Oz and Doug Mastriano only to watch them lose winnable general elections. He’s been trying to save face by touting successful endorsements he made in safe districts and states, but as the New York Times put it Thursday, "in 36 House races that the Cook Political Report rated as tossups, Mr. Trump endorsed just five Republicans. Each one lost on Tuesday." Oof.
Instead of providing momentum, Trump’s underwhelming showing suddenly has him on the ropes. Republican elites started turning on him as soon it became clear the red wave wasn’t materializing. In a remarkable turn of events, Murdoch-owned media outlets, including Fox News, the Wall Street Journal, and the New York Post, each published highly critical Trump pieces in recent days with brutal headlines like the one below.
Trump’s own advisers are going on TV and urging him to postpone the official announcement of his 2024 campaign, which he planned to do next Tuesday. Elected Republicans who used to support him are publicly saying they won’t do so again. Even Trump’s preposterous attempts to twist the midterm results into a victory for him have a whiff of weakness.
And while Trump’s star fades, a rival has emerged. Ron DeSantis’s blowout reelection victory stood in contrast to Trump’s struggles. Republican elites and right-wing media are rallying around him, and the mainstream press is pumping him up too.
In short, the prospect of a Trump-DeSantis primary is not only looming, but it seems more possible than ever that Trump could actually lose.
To get some expert perspective on the fall of Trump and rise of DeSantis, I talked to Ron Filipkowski. Filipkowski is a Florida-based lawyer and former Republican who was actually appointed by DeSantis to a panel that picks judges. He resigned from that role in December 2020, and since then has gained a large online following tirelessly tweeting videos of Trumpworld events and media appearances. He now describes himself as a Democrat.
Filipkowski told me that he never thought DeSantis would actually run against Trump — until Tuesday, which he described as a “game changer.”
But Filipkowski cautioned that liberals shouldn’t get overly excited about the prospect of DeSantis supplanting Trump atop the GOP ticket.
“I do believe in some ways DeSantis would be way more dangerous than Trump,” he said.
A transcript of our conversation, lightly edited for length and clarity, follows.
How much trouble is Trump in right now?
You really have to go back to what Lindsay Graham was talking about in 2016 when he said, ‘If we nominate Trump, we will get destroyed.’
I think what Graham was talking about is what's happening right now. I took his tweet as saying, ‘over the long term, he's gonna destroy our party.’
The Republican Party has been a 46 percent party for a long time now. Trump alienated three to five percent of that base and drove them out, including people like me, Lincoln Project guys, Bill Kristol — that whole crew of people. We’re representative of a sliver of the Republican Party that left because of Trump, and they can't afford to lose anybody.
But what Trump did was he brought in this big chunk of people that are now part of the party that never voted before 2016 and never contributed to any candidates. These are the people that you typically see at his rallies. And the problem with that chunk is that the Republicans now cannot win elections without that 20 percent of the party, and those people are loyal to Trump.
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The conundrum for the elite class of the Republican Party is how do they get rid of Trump and hang on to the 20 percent of the party that are Trump loyalists? That's the big trick for them. And that's why they're fixated on DeSantis. Not because he would be their first choice — I think they'd be more comfortable with a Pompeo, or Mike Pence, or somebody like that — but because they view DeSantis as the only viable option who could hang on to those Trump people.
And so the question is, is DeSantis capable of doing that, and will Trump allow that to happen? There’s only one scenario where I think they could pull it off — to get Trump to step aside for DeSantis.
Let’s hear it.
If I was advising them, which of course I'm not, here’s what I would do. I would wait until he’s indicted, which I think is gonna happen. I have always believed it was gonna happen after the 2022 midterms. I always believed it was gonna happen in December 2022. I still believe that. I don't know who's gonna be first, if it's gonna be Georgia, if it's gonna be the documents case, but it's coming. So I would wait until that.
He's probably gonna announce his presidential run next week — whatever, fine. But when he’s indicted, that's the game changer. And then at that point, Republican elites could call a meeting under the guise that they’re rallying around Trump to defend him against this unjust persecution. But in that meeting, you'd have to have a variety of heavy hitters, people like Rick Scott, Ronna McDaniel, Kevin McCarthy, Lachlan Murdoch, Sean Hannity, Matt Schlapp — people he listens to, respects, even has a little bit of fear of — presenting a united front. And they’d say to him, ‘Look, we're gonna stand by you. You're still the spiritual leader of the party. We're gonna pay your legal bills, we're gonna fight the DOJ. We're gonna have oversight hearings and go after them, and we're gonna let your PAC continue to raise money and you're still gonna be able to do all your endorsements. We still want you to do the rallies for our people, but you need to focus on staying out of prison. We really need you to step aside and be the kingmaker for us and get behind Ron.’
Presenting Trump with a united front like this would let him know that they’re done with him and would send the message he can’t win without their support. I see no other scenario to get Trump out of the picture.
DeSantis’s 2018 gubernatorial campaign was about the Trump cult of personality almost to an absurd degree. Who can forget the campaign ad showing his son building the border wall with toy blocks?
But it feels like DeSantis has successfully gotten out of Trump’s shadow since then. How has his political brand evolved?
DeSantis was very keenly aware that he absolutely owed his election to Trump in ‘18. There's no question that he would've lost the primary by 30 points without the Trump endorsement. But DeSantis doesn't like that fact. He knows it's true, but he hates that it’s true. And I think he’s spent every waking moment since 2018 distancing himself from Trump, trying to show he’s his own man and doesn't need him. It's why he didn't ask for his endorsement. It's why he’s never talked about January 6. It's why he has never talked about the 2020 election being stolen. This is also why the Republican establishment likes Ron DeSantis as an alternative.
What they care about more than anything else is winning — acquiring power. Not only can DeSantis possibly hang onto those Trump MAGA voters, but he's also not tainted like so many members of Congress — Ted Cruz, for example — by all of the Trump mania. Even on Covid, he distanced himself from Trump on the vaccine. So I think all of that was done in a very calculated way to try to separate himself from Trump.
We could go back and play all of DeSantis’s press conferences and speeches for the last year. I don't know that he's used the word ‘Trump’ ever. I don't remember hearing that name come out of DeSantis’s mouth. And Trump doesn’t say his name either.
Although Trump did refer to him as “Ron DeSanctimonious” the other day.
Yeah. It was always subtle slights before that, but now of course we've seen a couple overt shots. And I'll tell you what, I was watching MAGA online traffic when Trump said that and they were not happy about “DeSanctimonious.” They were pretty pissed. They didn’t like it because it was just so unnecessary and gratuitous. There was no reason for it. He just went out of his way to take a shot at him.
(Note from Aaron: As I was wrapping up this post Thursday evening, Trump upped the ante by publishing a string of Truth Social posts savaging DeSantis. Notably, in one of the posts, Trump seemed to brag about using his power as president to rig the 2018 gubernatorial election in DeSantis’s favor — which, if true, seems like a pretty big deal.)
Let’s assume for a minute that the Republican intervention you outlined earlier doesn’t work, and Trump ends up running against DeSantis in a primary. Do you think DeSantis would have a shot of winning, and what would that primary look like?
I've been saying for about the last two years that there's no way DeSantis would run against Trump in a primary, but I think the midterms just completely changed that. They were a game changer.