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.
“Great,” she said. “They’ve all been great, honestly.”
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.
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.
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.
Copyright 2026 The Associated Press. All rights reserved. This material may not be published, broadcast, rewritten or redistributed.
The Month in Photos: Sept. 2026
