Jon Stewart has turned Donald Trump’s unusually close relationship with Natalie Harp into a punchline with a sharper question underneath. The late-night host focused on whether Trump’s trusted aide should serve as a gatekeeper for information reaching the president.
Jon Stewart trolls Donald Trump and Natalie Harp in new monologue
On Monday, Stewart zeroed in on letters Natalie Harp sent Trump and described them as “love letters.” He then questioned the influence of a presidential aide who reportedly stays close to Trump and helps prepare some of his Truth Social material (via The Daily Beast).
“This is unbelievable,” Stewart said, arguing that information from the “outside world” appears to pass through Harp before reaching Trump. He then raised a more serious concern, saying, “Natalie Harp had repeatedly declined to get security clearances. Can we even trust her?”
Harp earns $150,000 annually as Trump’s executive assistant, according to the report, and Trump has reportedly awarded her gifts worth tens of thousands of dollars. Journalist Michael Wolff also published two letters she wrote to Trump in August. In one 2023 letter, Harp told him, “You are all that matters to me,” before thanking him for being her “Guardian and Protector in this Life.”
Stewart found another way to turn Natalie Harp’s reported “Human Printer” moniker into late-night material. The nickname stems from claims that Harp produces or prints flattering coverage for Trump, a label reportedly embraced by people in the president’s orbit. Ronny Chieng helped sell the gag by bringing an actual printer into the segment.
Stewart then shifted to The Matrix, comparing Harp’s position around Trump to the film’s blue pill: a way of staying insulated from an uncomfortable reality. He also brought Nathan Fielder’s documentary, You Can See Everything, into the routine, using altered footage to draw a tongue-in-cheek parallel with Theranos founder Elizabeth Holmes, who is in jail right now.
Seth Meyers had raised a similar objection in late August on his own late-night program. Meyers argued that Trump could access enormous amounts of information through government resources, yet appeared to rely heavily on Harp as a personal “pipeline to real information.”
