For Donald Trump, the initial plan seemed simple.
By agreeing to an exclusive town hall in New Hampshire with his biggest cable news nemesis—CNN—the 2024 Republican frontrunner was poised for a made-for-primetime clash to delight his followers, set off his critics, and suck up the political oxygen in the critical early primary state.
Just over 24 hours before Trump’s scheduled sit-down, however, whatever hopes he had to ambush CNN turned into what one of his former advisers called “walking into a complete ambush.”
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That’s because on Tuesday, a Manhattan jury found Trump to be liable for sexually abusing, and then defaming, the writer E. Jean Carroll, awarding her $5 million in damages.
Trump is almost certain to be asked about the case and the verdict by moderator Kaitlan Collins, who covered his White House for CNN.
“If I were on his communications team, I would be shitting my pants right now,” said the adviser, who held a senior role on Trump’s 2016 campaign and requested anonymity to speak candidly. The verdict, they said, “could not have come at a worse time for them, so I think this thing takes on a whole new dynamic. Majorly.”
It was unclear following the verdict if his campaign was trying to renegotiate the terms of the programming with CNN. One source close to Trump confirmed to The Daily Beast that he still planned to show. Representatives for CNN did not return a request for comment.
But the legal developments only supercharged the existing tensions and perils—for both parties—in deciding to do the town hall.
The former president hasn’t sat down on camera with a CNN journalist since Wolf Blitzer interviewed him in January 2016, shortly before he won the New Hampshire primary. And he’s done astonishingly few interviews, of any kind, with non-friendly media since his supporters stormed the U.S. Capitol on Jan. 6, 2021, or since he was criminally indicted in Manhattan last month.
Trump is liable to be confronted about it all, on live television, for the first time in years. Just before the Carroll verdict was handed down, he candidly acknowledged that the event was perhaps ill-conceived. In a post on Truth Social, he said it "could turn into a disaster for all, including me. Let’s see what happens?"
Many liberal commentators spent Tuesday afternoon calling for CNN to cancel the event and expressing disbelief that the network would give an exclusive platform to a man just found liable for sexually abusing and defaming a woman. But many also felt the same way when CNN was simply granting airtime to the only president in U.S. history to be criminally indicted or impeached twice.
Privately, CNN seemed to recognize other pitfalls on their end, too. The town hall format, with GOP and independent voters asking the candidate questions directly, was initially seen as much more of a gamble for CNN than for the Trump campaign, according to GOP operatives and sources close to Trump who spoke with The Daily Beast for this story.
One senior Granite State Republican said a representative for CNN tried to convince her to ask a question at the event because “they’re having a bit of an issue with women.”
“I said to her, ‘What do you think that tells you?’ Because they’ve lost a lot of the female vote,” the Republican told The Daily Beast, adding that she wasn’t surprised the bulk of questions submitted were from men.
Trump could have used the event to court the suburban women voters he’s steadily lost, “but he spent 70-some-odd years saying the things he does say about women and to women,” the woman added. “It’s too late for him to walk that back.”
The town hall, then, comes at a pivotal moment for both Trump’s presidential comeback bid and the media tasked with covering it. With an increasing polling lead over his GOP primary rivals, Trump is gaining surprising momentum with the party base, even as top party officials point to news like the Carroll verdict to argue that he’s as unelectable as ever.
What Trump says and does on Wednesday night on air at Saint Anselm College, in Manchester, could help define his relationship to his party as the primary contest gets more serious.
Convinced by top advisers to reappear on the network, Trump has been approaching Wednesday night as an easy way to contrast himself against both President Joe Biden and Florida Gov. Ron DeSantis. It’s also a chance to entertain his supporters.
Those close to the former president said he plans on going after CNN—a network he is still suing over “DEFAMING” and “SLANDERING” him—for their years of adversarial coverage. Since the lawsuit was filed in early October of last year, Trump has sent out countless email blasts fundraising off the suit.
Just as he did in 2016, Trump can generate a multi-day media cycle out of a confrontation with a major news outlet. “The guy is the most shameless PR master in the history of our country,” a GOP strategist without a horse in the 2024 race said. “Whether it’s always good for him, that’s another story. But in terms of generating raw press coverage, no one can do it like he can.”
One Trump operative close to the campaign said Trump has toyed with “flipping the script” on CNN by getting into a back-and-forth with Collins. One Trump adviser, the pastor Mark Burns, agreed, saying the town hall gives Trump the opportunity to “stand his ground” and fire back with his “quick wit” in “not-so-friendly territory” if he’s attacked—all with the understanding that the “hand of God is upon his life.”
Behind the scenes, according to close Trump allies and advisers who spoke to The Daily Beast, Trump has also been eyeing the possibility of attempting to create a “viral moment.”
“I’d tune in if I were you,” Trump campaign spokesperson Steven Cheung told The Daily Beast when asked about that prospect.
“He thrives from confrontation from the media,” founder of Pastors for Trump Jackson Lahmeyer said, citing Trump’s brutal and misogynistic attacks on then-Fox News anchor Megyn Kelly following the first GOP debate of the 2016 primary. The former Trump 2016 campaign adviser also drew parallels to the Kelly row, sympathizing with Collins for being in an even more difficult position following the Carroll verdict.
“I mean, how do you ignore the elephant in the room?” the Trump campaign veteran said. “You finally get this guy on TV, and this is ratings gold. No matter how much that Megyn Kelly moment backfired, those are the moments where somebody who has Trump participating live is gonna drop that kind of bomb.”
Several Republicans who spoke to The Daily Beast said Trump will need to be careful not to get too confrontational with voters who ask unfriendly questions—or with Collins, who cut her teeth at The Daily Caller covering the Trump 2016 campaign before covering his 2020 campaign, and all four years of his presidency, for CNN.
“She’s perceived as someone who’s been traditionally very tough to both Trump and Biden. It’s not like he’s going on Sean Hannity or something,” the GOP strategist said.
Collins was barred from press conferences in the Trump White House in July 2018, but continued lobbing questions at the president after the spat and covered him on myriad foreign trips.
Her presence as a female moderator, the Trump 2016 adviser said, compounds what’s become “a real messaging problem” for the Trump 2024 team. “Because the more they try to say another witch hunt and bullshit like that, especially if you couple it with this abortion thing… women are very turned off by this shit.”
Appearing on a network Trump has spent years deriding also has its risks among the base.
“They will stay fake news but will go up in viewership with our real President appearing!” MyPillow CEO and Trump ally Mike Lindell told The Daily Beast, struggling to square the two things. “Then their ratings will go back down!”
Notably, those close to Trump also see his return to CNN as a great opportunity to stick it to Fox News, now more unpopular than ever among the MAGA base.
"Not for nothing, if Fox hadn't fired Tucker Carlson, maybe we'd be seeing a different platform,” Michael Caputo, an outside adviser and longtime friend of Trump, told The Daily Beast. “I can't imagine anyone in Mar-a-Lago is too pleased with Fox right now. If they could take it off of all the TVs in there, I bet they would."
In the end, Trump’s closest allies—despite any hardcore MAGA blowback that might come their way—had been declaring the town hall as a victory before it even happened.
“President Trump is unafraid to take on the liberal media in order to speak directly to all Americans,” Karoline Leavitt, spokeswoman for Make America Great Again Inc., told The Daily Beast. “In a grassroots-oriented state like New Hampshire, President Trump's direct approach is much appreciated.”
Yet for other Republicans looking toward the general election, the potential for a meltdown over either the abortion issue or the Carroll verdict or anything else Trump could say at a random moment still looms large.
“Our party is already having trouble with women, and if there’s any candidate that’s gonna compound that trouble for us, it’s Trump,” said the New Hampshire Republican woman who declined CNN’s nudge to ask a question.
Those who’ve gotten off the Trump train also couldn’t help but rejoice a bit at the timing of the town hall and the verdict, where the jury found Trump guilty of sexual battery but not rape.
“Apparently,” the Trump 2016 adviser said, “you can’t grab ’em by the pussy."
