Stephen Colbert said he leaned into current events on The Late Show after initially planning to be less political after leaving The Colbert Report. Speaking to The New York Times this week, Colbert explained that when he took over for David Letterman in 2015 CBS discouraged him from “being topical.”
“It was my instinct to be less topical, because I didn’t want to have to engage with what I saw was an increasingly contentious public discourse,” Colbert said. “And I thought, aren’t there other ways to have fun with the audience?”
After a few months, though, he began introducing more political jokes. “I was like Clint Eastwood in Unforgiven, or is it some other movie? He buried his guns,” Colbert recalled. “And I’m like, you know, I buried those damn guns. I was talking to Paul Dinello — he’s one of my oldest friends and one of my producers here — and he’s like, ‘You’re having fun, and people love to see that.’ And I said, ‘But that means I got to go dig up the guns.’ And he says, ‘Buddy, that’s the part the audience wants to see.'”
Being political has, of course, drawn the ire of the Trump administration. Colbert said that he believes that’s because “authoritarians don’t like anybody who doesn’t give them undue dignity.”
“Comedians are anti-authoritarian by nature,” the host noted. “And authoritarians are never going to like anybody to laugh at them. The number of newspeople who have said to me or Jon Stewart or any of the guys who do this, ‘God, I wish I could say what you say on air.’ And we can. I think that upsets them. I think it might be upsetting that we really do not live in their world of principalities and powers.”
He added, “I don’t have any problem with Trump being a Republican. I have a problem with Trump being a complete narcissist who is only working for his own interest and does not appear to care if the entire world burns. That’s not a partisan position.”
Last year, CBS announced it was cancelling The Late Show, citing the decision as a “financial” one. The final episode will air on May 21. It’s been speculated that CBS’s parent company Paramount pulled the plug to curry favor with Donald Trump and the FCC to ensure a merger between Paramount and Skydance would go through.
“I do not dispute their rationale,” Colbert said about CBS. “I do make jokes about it. But I also completely understand why people would say (a) that doesn’t make sense to me and (b) that seems fishy to me, because the network did it to themselves by bending the knee to the Trump administration over a $20 billion, settled for $16 million, completely frivolous lawsuit.”
He added, “It’s possible that two things can be true. Broadcast can be in trouble. They cannot monetize because of things like YouTube, because of the competition of streaming. They’ve got the books, and I do not have any desire to debate them over what they say their business model is and how it does not work for them anymore. But less than two years before they called to say it’s over, they were very eager for me to be signed for a long time. So, something changed.”
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Natalie Harp with Donald Trump on July 22, 2026.
Nothing About Trump and Natalie Harp Is Normal
In early 2024, while reporting a story on New York’s boisterous, controversial Young Republican Club, one of my sources told me they had a pretty direct line to Donald Trump himself.
At the time, Trump wasn’t president again — yet. But he was campaigning, and in order to get something in front of his eyes you had to first get the attention of someone else: his assistant and right-hand woman, Natalie Harp.
Harp, 35, is now at the center of a major media frenzy, as Democrats like Georgia Senator Jon Ossoff have seized upon her unusual relationship with her boss: part assistant, part hype-man, part gatekeeper. On Sunday night, Ossoff made a comment that many interpreted as an insinuation that Harp had a more personal relationship to the president.
“The president sleeps through his meetings. He golfs and trades stocks,” Ossoff said at a campaign event in Georgia. “See he doesn’t want to do the job. He wants to build his ballroom and travel with Natalie on their apparently defenseless flying palace gifted by the Emir of Qatar.”
Ossoff’s comments set off a firestorm both in Democratic circles and the GOP’s reactionary messaging apparatus.
“Jon Jackoff has to be the biggest cuck loser in politics,” Steven Cheung, the White House communications director, posted on Monday morning. By Tuesday, the entire media ecosystem had weighed in — with some coming right out and saying what they thought Ossoff was implying in his joke, and detailing why it was out of bounds.
“Ossoff was clearly implying that Trump was having an affair with his staffer,” Megyn Kelly wrote on X. Florida Congresswoman Anna Paulina Luna called him a “sexist arrogant jerk.” Pundit Robby Starbuck wrote that “Ossoff is a vile coward for insinuating they’re having an affair.” The flood of backlash poured out of just about every conservative commentator you could think of.
The White House joined the fray after CNN posed a question about Harp to Trump, asking him to respond to Ossoff’s comments directly. “You mean Pee-Wee Herman?” Trump quipped in the moment, referring to Ossoff. His comms team went for a full broadside later online. “Someday, your children will come across your disgusting and inhumane question,” Trump’s rapid response account posted at CNN reporter Kristen Holmes. “They will be sickened and embarrassed to have a parent be so callous and vindictive. It’s quite troubling.”
Ossoff, meanwhile, tried to soften the blow of his joke, redirecting it — sort of — away from Harp herself to make it more of a comment on the president’s relationship to his staff in general. “I’ve heard this particular aide referred to as his security blanket,” he told Jen Psaki on MS NOW. “And I think we could say that about any number of the senior aides in the White House.”
But the damage was done, and it’s hard to believe Ossoff didn’t know exactly what he was doing. In recent years, some Democrats have occasionally flirted with the type of mud-slinging that Trump and his imitators became known for, but they’ve rarely landed a hit that provoked this much of a reaction.
“What a coward. Own your sexist joke, bro,” right-wing commentator Scott Jennings posted.
Harp’s history — and her relationship to the president — give some clues as to why the Republican beehive is so agitated.
Harp began her career in the public eye as an anchor for One America News, a right-wing propaganda outlet that was founded in 2013 and became something of a mouthpiece for the Trump administration and then the MAGA movement during the Biden administration. Democrats and liberal commentators have pointed out that Harp was often fawning over Trump during her segments.
While these clips have been used as more evidence that Trump and Harp have a strange dynamic, it’s hard to say that this kind of content is outside of the norm for OAN’s programming at the time. But that doesn’t mean Harp’s history with Trump isn’t strange — even by MAGA supplicant standards.
At the 2020 Republican National Convention, she said she was a bone cancer survivor and credited her survival to a “Right to Try” policy pushed by Trump in 2018 that allowed patients to use experimental drugs.
“When I failed the chemotherapies that were on the market, no one wanted me in their clinical trials,” Harp said at the RNC. “They didn’t give me the right to try experimental treatments, Mr. President. You did, and without you, I’d have died waiting for them to be approved.”
The Washington Post, however, notes that the drug Harp used was already approved by the FDA — which would have meant that the “Right to Try” law wouldn’t have applied.
Still, it’s clear that Harp feels a close personal connection to Trump. After her short stint at OAN, the Post cited her as a Trump employee as early as 2022. In 2024, The New York Times reported that Harp’s primary role on Trump’s staff was what other aides called “the human printer” — following Trump around with a battery powered printer so she could give him physical copies of social media posts, missives, text messages, and positive, often conspiratorial news stories. The Post story in 2022 also detailed her in this role, noting that other aides were “particularly distressed” by her access to and influence with the president.
“She is indicative of the people around him who just love him,” one anonymous adviser told the Post in 2022. “Love him too much.”
The Times’ reporting also noted that Harp’s esteem for Trump was particularly fervent, describing how she wrote him a series of what the newspaper called “devotional letters,” one of which said: “You are all that matters to me.” The Times described her running behind Trump’s golf cart, reading him social media posts and news articles. Following one of those instances, the Times reports that she wrote him another letter, apologizing for being “an embarrassment” while on the golf course in Scotland. “I want things to always be right between us,” she wrote. “I also know I’ve been distracted all week (forgetting to eat throughout the days, and even forgetting to sleep, and only catching a couple hours at a time).” Harp signed the letter, “With all my heart, Natalie.”
Harp’s family have acknowledged that her relationship to Trump is not that of a traditional staffer. In an interview with CNN on Tuesday night, Harp’s estranged brother Preston Harp said that “Since she was 16 she’s had an obsession with – she’s written letters to other presidents, let me put it that way,” Preston Harp said, mentioning “George Bush during the Iraq War” and that “her dream came true finally.”
These details are certainly odd, but so is basically everything about the particularities of Trump’s inner circle. Ossoff’s comment, however, likely came at least partially in response to another outlandish story that broke earlier this month.
On August 10, the Post reported that Trump had covertly switched planes during a trip to Turkey, hiding in an airline catering truck with a tiny group of aides in order to dodge a potential attack on Air Force One by Iranian proxies. The White House press corps and several key government figures — including Secretary of State Marco Rubio — stayed on board the “decoy plane.” Harp did not. She was reportedly in the food truck with Trump.
It’s impossible to know the exact nature of Harp’s relationship with Trump. Ossoff did not specifically mention an affair, though it’s hard to interpret his familiar comment as anything else — and the right-wing media is reacting to it as such, trying to take a moral high ground on behalf of a president who has, at least in civil court, been found liable for sexual abuse on at least one count, and routinely makes sexist comments toward female reporters and others.
Jesse Watters of Fox News was one of the only right-wing commentators to recognize the hypocrisy of bashing Ossoff’s comment while supporting Trump: “Am I fazed by this comment? No. Has Trump said so much worse, so much more sleazy things against other people? Yes. Have I defended those things? Absolutely. So, I’m not going to pretend to be all hot and bothered by it.”
Watters is an outlier, though. No matter what the charges, Trump will always have his protectors in the GOP, some more loyal than others. In recent years, Natalie Harp has been more loyal than anyone else.