Politics

Why Trump’s Got Reasons to Slip Natalie Harp Cash: Author

HUMAN MONEY PRINTER

Trump’s suspicious gift may have come with a condition, his biographer said.

Donald Trump’s eyebrow-raising cash gift to his fawning aide could have come with strings attached, his longtime biographer suggested.

Appearing on the Inside Trump’s Head podcast, author Michael Wolff theorized that the president’s $45,000 “Cash Gift for Holidays” to his 35-year-old assistant Natalie Harp was not just out of the goodness of his heart.

“Why are they getting this money? It’s the classic rhetorical question,” Wolff told host Joanna Coles. “There isn’t an answer, except that I think I have an answer.”

“I know that in the past, in other situations, Trump has come up with amounts of money at certain moments when he felt that he was not... covered enough by the NDAs in place,” he continued, referring to nondisclosure agreements. “So essentially, he is buying a further NDA.”

Trump
Trump has used his money to make others stay quiet before, Wolff said. Eric Lee/REUTERS

“This is commonplace in business. You... sign an NDA because you’ve been given something,” the author added. “As a matter of fact, it’s hard to enforce an NDA when you have not been given something. It’s a transaction.”

Harp, who makes $150,000 a year as the president’s special and executive assistant, received a cash gift worth nearly a third of her salary, The Washington Post reported late Tuesday, citing financial disclosures released by the government.

natalie harp
Government documents revealed Harp accepted a $45,000 cash gift from her boss. Nathan Howard/REUTERS

Trump, 80, also paid out large sums to two other young aides: Margo Martin, 31, and Chamberlain Harris, 26. His director of Oval Office Operations, Walt Nauta, also received a $20,000 holiday gift.

White House spokesperson Davis Ingle told the Post that Trump “has a longstanding practice of giving Christmas gifts to people in his orbit,” but experts say a sitting president giving gifts of this magnitude to employees is unprecedented.

Donald Trump and Margo Martin at Trump National Bedminster.
Donald Trump and Margo Martin at Trump National Bedminster. Vincent Carchietta/USA TODAY Sports via Reuters Con

Wolff said Trump has used the NDA route before with others who had inside access to his “very small bubble,” and that Harp was no different. However, he said Trump’s presence in the White House complicated things.

The author said that though NDAs are common in government work, enforcing the contracts is “very problematic.”

Natalie Harp, aide to US President Donald Trump, looks on as President Trump visits the Mission Control Center at NASA Lyndon B. Johnson Space Center in Houston, Texas, on August 28, 2026.
Wherever Trump goes, Harp is not far behind. KENT NISHIMURA/AFP via Getty Images

“How do you enforce an NDA when you’re in a political situation?” he asked. “You’re essentially on the payroll of the United States government—the people’s payroll, you might say.”

Wolff added that he doesn’t know whether or not the cash gifts were paid out with taxpayer money.

“If this were a matter of getting... a transaction that got you an NDA, that would probably be relevant where the money comes from,” he said. “But I don’t know... This is my theory... of the case based on what he has done in the past.”

The Daily Beast has reached out to the White House for comment.

Find and subscribe to Inside Trump’s Head with Michael Wolff and Joanna Coles on YouTube and wherever you get your podcasts. New episodes of incomparable insight into the psyche of the world’s most talked-about man drop every Tuesday, Thursday, and Saturday evening on YouTube and Wednesday, Friday, and Sunday mornings on other podcast platforms.