To Be or Not to Be: Trump’s Big 2024 Question

Donald Trump at the Evander Holyfield fight
Photo by Douglas P. DeFelice/Getty Images
Tina Nguyen
September 13, 2021

It was entirely predictable that Donald Trump would engineer a telenovela-style storyline to sustain interest in his will-he-or-won’t-he plot to potentially re-assume power in 2024. For every move that he makes demonstrably indicating another run for president—holding campaign-style rallies, for instance, or uttering coy remarks in interviews, or even dropping thinly-veiled smoke bombs in super PAC email blasts to put ambitious Republicans on notice—Trump also makes dramatic zags away from campaign politics, yawing towards a more lucrative post-presidential life. Such is the nature, of course, of a supremely undisciplined superego reaching for the levers of power and attention in a post-Twitter and post-White House existence. And it’s also the result of neutered, powerless Republican establishment fearfully overthinking a political moment rather than defining it. Again, it was entirely predictable. But what comes next?

Trump, to his credit, has not made the parlor game surrounding his future easy to surmise. One week, his former chief of staff is telling Fox News about a “shadow cabinet” within Mar-a-Lago; the next, Trump convenes a dinner of election fraud conspiracists. Trump began the somber anniversary of 9/11 at a fire and police station in New York, where he teased another presidential run—“I think you’re gonna be very happy”—before flying down to a South Florida casino to oversee the “comeback,” and eventual drubbing, of 58-year-old boxing legend Evander Holyfield. In between, he appeared in a taped video to address the Korean “Moonies cult,” known for its mass weddings and support for right-wing political groups.

It was a delirious sequence of events, beneath the dignity of a former president and yet totally, authentically Trump. Could it be that he has already decided, deep down, that he will trade in another run at the White House for a return to showbiz or a litany of who-gives-a-fuck bucket list fantasies like hanging with the guy who had his ear chewed off by Mike Tyson? Or, by the dialectic of Trumpian self-promotion, are they one and the same? 

These tactics are not unfamiliar in Hollywood. Call me a Marvel nerd, but I was reminded this week of the rumors that Tobey Maguire and Andrew Garfield might appear with Tom Holland in Marvel Studios’ upcoming Spider-Man movie. Three Peter Parkers in one film would be an ambitious cross-over cinematic event. Marvel has denied it. The actors have denied it strenuously in interviews. But a slow drip of gossip leaking into celebrity blogs, and blurry photos of the former Spider-Men tooling around an Atlanta sound stage, have built sky-high hype over the possibility. Regardless of whether Maguire and Garfield show up, the media buzz will have done its job—and Marvel Studios should continue printing money.

I believe that’s what’s happening here, too. And I’ve seen it in my travels across the country, and in conversations with dozens of sources in Trump’s orbit. Although Trump was never known as a savvy geopolitical mind or legislative operator during his time in the White House, the interregnum before the deadline to register for the New Hampshire primaries, likely sometime in November 2023, has opened a new chapter of the Trump Show, one that plays directly to his strengths: fueling outrage, filling his cup, and keeping his brand alive, ready for whatever he decides to do at the very last minute.

Trump has a number of perfectly viable reasons to run, according to everyone I’ve spoken to. He enjoys combat as much as he relishes winning, and would welcome a rematch against Joe Biden, these people say. He’s also the overwhelming favorite of the Republican base; and, according to these people, he misses the rallies and requires adoring crowds to keep his political groups (and legal funds) full of cash. The rejoinders, and his obvious political weaknesses, can all be answered with some creative MAGA magical thinking: Sure, he would be 78 by the time he was hypothetically sworn in—but that’s how old Biden was when he ran. Trump could be entangled in the various investigations into the Trump Organization—but the accusations could be leveraged by forces on the fringe right to turbocharge a potential campaign against the “deep state,” aligning Trump with the January 6 rioters, in the view of his supporters, as an oppressed political class. (Representatives for Trump did not return a request for comment.)

Anything Trump does in between now and Iowa, in the meantime, can best be described as brand maintenance. Even, yes, his decision to join the Pay-Per-View broadcast of an insensitively-timed boxing match full of has-been fighters. “If you’re looking at it through the lens of what a normal politician does to get ready for a political campaign, you’d look at it and say, this person is clearly not running for office,” a close Trumpworld advisor told me. “Why is he color commentating a celebrity boxing event?” 

But, the advisor added, there was a subtle, if Trumpian, logic at play. Trump’s trek to celebrity wound directly through combat sports—Wrestlemania, celebrity boxing matches, Atlantic City—and the Holyfield match also featured UFC talents Vitor Belfort, Anderson Silva, and Tito Ortiz. Not only is Trump close to UFC president Dana White, but the combat sports audience generously overlaps with his base. “I wouldn’t say this is proof positive that he is running,” this insider continued, “but connecting at a cultural level has always been the secret sauce of Donald Trump, and events like boxing, UFC, and pro wrestling—all these things have something in common, which is that it’s often looked down at by the smart set.” 

Trump’s other extracurricular maneuvers, too, might veer back and forth between the political and personal, but that was always the Trump brand. This is, after all, a man who openly told foreign dignitaries to stay at his Trump-branded properties, whose officials hawked Ivanka Trump clothing in press conferences, and whose Twitter account literally posted an advertisement of Goya canned foods on the Resolute Desk. So a dip into something lowbrow and commercial is neither a sign that he is giving himself over to red state prurient delights nor that he is playing Vulcan chess with the electorate. It’s just more of the same power-equivocating that led the man down the golden escalator and to the White House in the first place.

The Trump calculation would obviously be different if his potential challengers weren’t waiting on the sidelines to see what he does next: Kristi Noem, Ted Cruz, Marco Rubio, Tom Cotton, and yes, Ron DeSantis, have been spotted at fundraisers and swing states across the country, meeting with the party’s movers and shakers. And with increasing reports of 2024 hopefuls sniffing out pockets of support in early voting states, Trump’s Save America PAC—an organization whose email blast has replaced his Twitter feed—has begun to build a moat around the base. The organization recently sent an email to supporters pointedly alerting them to an Emerson poll that showed Trump winning a commanding 67 percent of potential G.O.P. primary voters. DeSantis, who sat atop six other challengers, only received 10 percent of the vote. 

Already, however, the narrative groundwork is being laid for a death match between Trump and DeSantis, the Florida governor who many in the party view as a potential Trump alternative: younger and with less baggage, a never-masker who has a strong fandom among MAGA supporters on his own. Though DeSantis’ star shot up dramatically after Trump endorsed him, numerous reports have recently started chronicling the gossip leaking out of Florida about their growing feud, and Trump has begun publicly suggesting that DeSantis’s career would be nowhere without him. (DeSantis has denied the beef.)

Alex Breusewitz, a political consultant who works primarily with far-right candidates and the Stop The Steal movement (the group that organized a rather unruly rally for Trump on January 6th), quickly swatted down the idea that DeSantis could take on a fully-engaged Trump. “Ron is very beloved among Trump voters and the Trump base. But there is a loyalty among Trump voters in the Trump base, to Trump,” he told me. “And so if they become opponents, DeSantis is going to quickly realize that those people that promote him all across the country right now, that are waving Trump/DeSantis 2024 flags, they’re gonna go right back towards Trump. And it’s not going to be a competitive matchup.” 

That observation could apply to every potential Trump opponent within the party, and demonstrates the power that his brand loyalty commands among the core of the G.O.P. these days. And frankly, it would be hard to imagine DeSantis shooting someone on South Beach in broad daylight and not losing a single vote.

There are, of course, some black swan events that could occur between now and the deadline to file for the primaries. Trump could fall into ill health, or see his legal jeopardy exacerbate—both possibilities that would automatically take him out of the race. But it is undeniable that Trump’s current activities are all focused on bolstering the Trump political brand, which was always, and continues to be, a singularly bizarre mashup of political nativism and unapologetic commercialism. 

In my conversations with people in Trump’s current political orbit, no one thought that this path would harm his political viability in any way. And some keyed in on a quickly forgotten political dynamic of 2020 that will likely change in 2024. Biden has tepid support, at best among, Democratic voters. His campaign was laggard until South Carolina, and benefitted both from a once-in-a-generation Pax Democratica in the general election, plus a phenomenal surge in mail-in balloting among liberals. Absent that constellation of events, Biden may be uniquely vulnerable to a contest of enthusiasm, even against a legally challenged amateur boxing commentator with a side hustle fueling insurrectionist conspiracy theories. “If [Biden] runs without Covid and mail balloting, how do you get the turnout that they need?” one G.O.P. pollster rhetorically asked me, reminding me that despite Covid restrictions, Trump was able to turn out a record-setting 74 million voters, the majority of whom voted in person. 

“Never forget this: the entire cycle of 2020, we were tracking the lack of intensity of support behind Joe Biden,” the pollster added. “His positive intensity was always a full 10 points less than Trump’s positive intensity. So the mail balloting and all of the extraordinary means in which you can get people to vote—if those are not permanent fixes for the Dems, they’re going to have a hard time getting Dems off their asses to vote for that old man.”

In the meantime, Trump’s brand has meant that he can do whatever he damn well pleases, and he seems to be reveling in it. Just look at how he made out from Saturday’s boxing match: he  made “millions and millions” of dollars to commentate that fight, if you believe what anonymous sources tell TMZ, and, more important for his ego, he walked out into a crowd chanting “We want Trump!” and “Fuck Joe Biden!” The entire time, he was grinning like a jack-o-lantern.