White House insiders are raising serious concerns about President Donald Trump’s relationship with Natalie Harp, his 35-year-old executive assistant, according to CNN senior political analyst Maggie Haberman. Speaking on CNN’s OutFront on Wednesday, August 19, Haberman disclosed that Harp “is not beloved by a lot of her colleagues” and that there has been “a lot of controversy around Harp’s role for a while.”
Haberman further revealed that foreign leaders seeking access to the 80-year-old president now use Harp as a back channel when traditional diplomatic routes prove unsuccessful.
The scrutiny intensified after Georgia Sen. Jon Ossoff, 39, called out Trump during an Atlanta rally on August 16, 2026, accusing the commander in chief of wanting to “travel with Natalie on their apparently defenseless flying palace gifted by the emir of Qatar.” The remarks triggered widespread MAGA backlash and reignited questions about the former One America News personality who shadows Trump’s every move.
Harp has also surfaced as a possible successor to outgoing White House Press Secretary Karoline Leavitt, whose departure is scheduled for the end of August. Prediction markets have floated her as a possible successor: Kalshi put her at 13 percent on August 13, behind front-runner Anna Kelly, and the field has shifted since.
Weekend Golf Appearances Fuel Speculation
On August 16, Harp made her second straight weekend appearance at Trump National Golf Club in Bedminster, N.J., dressed in vivid blue golf wear and clutching her signature oversized red bag. MAGA influencer Michael Solakiewicz posted video footage showing her walking mere paces behind the president as he interacted with young golfers at the New Jersey property.
The previous weekend, she had celebrated her 35th birthday at the same venue while Trump watched the final round of the LIV Golf tournament. She flew back to Washington on Sunday alongside acting intelligence chief Bill Pulte, red bag in hand.
Cameras also caught her boarding Marine One in August near the White House, red backpack strapped on, as Trump headed west for stops in Los Angeles and Las Vegas. The Los Angeles leg included an RNC fundraising event at his Rancho Palos Verdes golf property.
Emotional Support and Controversial Access
Her official job description barely captures the scope of what Harp does. The executive assistant attends Oval Office meetings, handles Trump’s social media late at night, and carries a portable printer to deliver hard copies of articles — earning the monikers “human printer” and “human binkie.”
Haberman described Harp on MS NOW Sunday as Trump’s emotional support during moments of high stress, calling her “his comfort blanket.”
During the fiery Atlanta speech, Ossoff lambasted Trump for focusing on personal luxuries while sailors fight in combat zones and national resources dwindle. He criticized the president’s desire to build his ballroom and fly with Natalie aboard an insufficiently defended plane given by Qatar’s ruler.
Political commentators Mehdi Hasan, Ron Filipkowski and Adam Carlson circulated the speech online. Michigan State Senate Majority Whip Mallory McMorrow responded, “Ok I’ll bite. Who’s Natalie.” Jeff Storobinsky, who hosts a podcast, raised the question of why Melania Trump would remain in her marriage. Harp appeared in the background of a social media image posted by Lara Trump, wife of Eric Trump, gripping two cellphones and papers.
Handwritten Notes and Secret Evacuation
Public interest in Harp surged after New York Times reporters Maggie Haberman and Jonathan Swan published “Regime Change,” which disclosed that Trump told aides Harp was the only individual who loved him as deeply as his spouse and children, and he forecast she would stay loyal forever. She allegedly left handwritten notes in his private quarters; one read, “You are all that matters to me.”
After intelligence confirmed a genuine Iranian plot targeting Air Force One, the Secret Service executed a clandestine departure from Turkey. Trump left on a C-32A with only a skeletal team: Harp, Deputy Chief of Staff Dan Scavino, and former valet Walt Nauta. The decoy aircraft carried Secretary of State Marco Rubio, senior adviser Stephen Miller, other high-ranking officials, and the press pool.
Family and White House Concerns Mount
Preston Harp, Natalie’s estranged brother, described the dynamic as unhealthy and likened his sister to a fan club. He attributed her intense devotion to their childhood, telling CNN’s Erin Burnett on August 18 that both were homeschooled and raised on American exceptionalism. He stated Natalie interprets what detractors call historical whitewashing as valid correction, mirroring Trump’s own perspective.
Haberman and Swan reported in “Regime Change” that even Trump’s closest advisers have expressed alarm. The Secret Service cautioned that officials considered Harp’s attachment a potential threat to both her own safety and the president’s. The White House has not issued a response to comment requests.
CNN pundit and former Democratic congressman Max Rose added fuel to the controversy on CNN’s OutFront, suggesting Trump is physically incapable of having an affair due to health reasons.
