Who’s on Air Force One? Trump’s midterms entourage includes strategists, aides and aging athletes
Oct 25, 2026, 5:31 AM
White House chief of staff Susie Wiles and White House aide Natalie Harp walk to board Air Force One, Friday, Oct. 16, 2026, at Joint Base Andrews, Md. (AP Photo/Mark Schiefelbein)
Credit: AP Photo/Mark Schiefelbein
(AP Photo/Mark Schiefelbein)
ABOARD AIR FORCE ONE (AP) — President Donald Trump has clocked about 70 hours aboard Air Force One so far this month, racing from rally to rally across the United States to try to bolster his Republican Party in the midterm elections.
Also along for the ride: an entourage ranging from aging boxing champions to Cabinet members to relatively unknown aides who help craft Trump’s words and ideas. The passenger list for Trump’s marathon through the sky signals who has the ear of the president.
“It can say what his priorities are,” said David Cohen, a professor of political science at the University of Akron. “Who he surrounds himself with are the people he is going to be listening to. They’re the ones who are going to be whispering in his ear and talking softly in private quarters to the president of the United States.”
Here’s a look at who has had access to power in the confines of Trump’s plane this month.
White House chief of staff Susie Wiles, who recently finished treatment for breast cancer, is a frequent flyer. Trump has called Wiles, who co-managed his 2024 campaign, the “most powerful woman in the world.” As Air Force One ascended from Greenville, North Carolina, after Trump’s 15th rally in 20 days, Wiles gave reporters her take on how it went as she walked up the aisle.
“Great,” she said. “They’ve all been great, honestly.”
Other insiders who’ve made the manifest: special envoy Steve Witkoff, who has been trying to negotiate an end to the Iran war that has weighed on Republicans’ midterm fortunes; deputy chief of staff Stephen Miller, the architect of Trump’s immigration crackdown; Housing and Urban Development Secretary Scott Turner; Treasury Secretary Scott Bessent and Agriculture Secretary Brooke Rollins.
The most frequent Cabinet member aboard has been Commerce Secretary Howard Lutnick, a billionaire who previously ran the financial services firm Cantor Fitzgerald. A Trump buddy going back to the 1990s, Lutnick can often be heard laughing at the president’s jokes. His role at Trump’s rallies has been to highlight new factory investments that Trump uses to try to convince his supporters that the economy is doing well.
Bill Pulte has joined Trump for at least five legs of the midterm marathon so far, a sign that his status inside the administration is far higher than his title — director of the Federal Housing Finance Agency — would suggest.
The scion of a homebuilding company, Pulte is a Trump pal who was for a brief period also the acting director of national intelligence and oversaw layoffs in that office. He has led pressure campaigns on Federal Reserve officials such as Jerome Powell and Lisa Cook. Pulte has also passed along policy ideas such as changing the 30-year mortgage to 50 years, an idea that has since been abandoned.
Federal Communications Commission Chairman Brendan Carr has also flown with the president, notably on Oct. 13 and Oct. 14 on a lengthy West Coast swing. Carr has sought to use his regulatory powers over broadcast networks to chastise them over their coverage of the president.
Chief among the retinue of assistants around the president is Natalie Harp, an executive assistant who is on most of Trump’s trips. Walt Nauta, the director of Oval Office Operations, is not far behind her in air miles. Chamberlain Harris, Nauta’s deputy, is another frequent traveler. She also serves as a member of the Commission of Fine Arts, one of the government bodies with a role in reviewing the White House ballroom and other Trump construction projects.
Although Trump likes to ad-lib, the speechwriting director, Ross Worthington, has joined him repeatedly on the plane this month. The president’s stump speech features a promise of $5,000 checks if Republicans keep their House and Senate majorities after the Nov. 3 election. He also tends to highlight new factory projects and investments in the communities he visits.
Margo Martin, a communications adviser who posts videos of Trump on social media, has joined the tour, as has White House communications director Steven Cheung. Katie Zacharia, who was the White House press secretary for five days, spent two of them with the president on a trip to Alaska, Nevada, Arizona and Montana.
Trump is surrounded on these trips by White House and external consultants making strategic choices for the midterms, including Matt Brasseaux, his political director, who previously worked at the Republican National Committee.
Johnny DeStefano, who was a top aide in Trump’s first term, temporarily rejoined the White House this summer to work on midterm strategy and has been seen on Air Force One, as has former White House deputy chief of staff James Blair.
Going into what could be some rough midterm races, Trump has brought aboard with him some of the biggest names in boxing: Mike Tyson,Floyd Mayweather Jr. and Evander Holyfield. In a 1997 heavyweight championship bout, Tyson bit off a piece of Holyfield’s right ear. They did not fly on Air Force One at the same time.
Towson University professor Martha Kumar said that presidential travel during a campaign can be intense and that presidents often have passengers who can keep the environment relaxed even as the work continues. “You want to have people around you that make you feel comfortable,” Kumar said. “When you think about it, it is really stressful. You want some relief.”
Who else has hitched a ride with Trump? Retired NASCAR champion Richard Petty went to North Carolina, former NFL coach Jon Gruden to Ohio, and retired NFL running back Todd Gurley to Georgia. Influencer-turned-boxer Jake Paul also traveled with the president. The celebrities have had cameos in Trump’s rallies.
The goal of Trump’s travel over the past month has been to help Republicans keep control of Congress.
As the White House’s liaison with the House, Jeff Freeland has been on Air Force One with multiple lawmakers. Rep. William Timmons of South Carolina flew with the president, as have multiple Texas House members, including Reps. Beth Van Duyne and Brandon Gill, as well as Reps. Brian Jack of Georgia, Tim Moore of North Carolina and Anna Paulina Luna of Florida.
John Barrasso of Wyoming, the second-ranking Republican senator, has flown multiple times with the president this month, as has Texas Sen. Ted Cruz, who is considering a presidential bid in 2028.
