Rosie O’Donnell Goes There With ‘Natalie’ Dig at Trump

‘NIGHTY-NIGHT!’

O’Donnell eviscerated Trump and his devoted 35-year-old assistant.

Rosie O’Donnell didn’t mince her words when it came to Donald Trump and his exceptionally loyal aide, Natalie Harp.

With rumors increasingly swirling about the president and his 35-year-old executive assistant, O’Donnell decided to go there on her third night of hosting Jimmy Kimmel Live!

“A special hello to those of you watching from home and from the White House,” the former host of The View and sworn Trump nemesis began.

“But I do have some bad news for President Petty Roosevelt,” she continued.

“That’s all I’m going to say about you tonight, sweetheart. You got to realize it’s time to hang up your wig and let Natalie tuck you in,” O’Donnell quipped. “Time to go nighty-night!”

Natalie Harp, Donald Trump
"It’s time to hang up your wig and let Natalie tuck you in!" O'Donnell quipped. MANDEL NGAN/AFP via Getty Images

Throughout her week as one of Jimmy Kimmel’s guest hosts, O’Donnell has kept her mentions of the 80-year-old president surprisingly minimal.

O’Donnell and Trump have a longstanding feud that dates back to 2006 and has only intensified in recent years. Kimmel tapped O’Donnell as a “special treat” for Trump. The late-night host himself has become a known adversary of the president, who has repeatedly called for Kimmel to be fired by ABC.

The partnership between O’Donnell and Kimmel was only apt. O’Donnell said she plans on “honoring just how brave and bold” Kimmel has been during her stint as the show’s anchor.

Rosie O’Donnell on Jimmy Kimmel Live
Rosie O'Donnell ripped into Trump in her first monologue, saying, “You know, right now he’s in the White House crying because I haven’t mentioned him.” ABC/Randy Holmes

But O’Donnell has surprised viewers by spending her monologues opening with a dig at the president and spending very little time on him otherwise. She has not even said his name, using creative nicknames instead: on Tuesday night, for example, he was “President Oompa J. Loompa.”

The dig about Natalie Harp is as vicious as O’Donnell has gotten so far.

U.S. Interior Secretary Doug Burgum and Executive assistant to U.S. President Donald Trump Natalie Harp speak with Donald Trump during a visit at a golf course at Hains Point in Washington, D.C., U.S., June 28, 2026.
Harp having a whale of a time with her beloved Trump in June. Ken Cedeno/Reuters

Harp has been ever-present at Trump’s side and is widely known for her devotion to the president, which has not gone unnoticed.

Democratic rising star Sen. Jon Ossoff made headlines for eviscerating Trump and Harp at a rally, saying that the president would much rather “travel with Natalie” and spend his time working on his beloved ballroom than carry out his duties as president.

Harp, who earns $150,000 a year as special assistant and executive assistant to the president, has become Trump’s constant companion just as his third wife, Melania, has slipped away from the public gaze.

Natalie Harp
Natalie Harp, always by Trump's side, has sent letters to the president with the sign-off “With all my heart, Natalie." Daniel Heuer/REUTERS

The first lady has appeared in public just 38 days this year, according to a Daily Beast audit of her calendar.

Melania’s exceptionally low number of public appearances has been offset by Harp being nearly inseparable from Trump at both private and public events, raising eyebrows. Both the president and his middle son, Eric Trump, have jumped to Harp’s defense amid the heightened scrutiny.

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