Trump's Air Force One Entourage Reflects Inner Circle for Midterms

President Donald Trump has spent approximately 70 hours aboard Air Force One this month, traveling to numerous rallies across the United States in support of Republican candidates in the midterm elections. The composition of his travel companions offers insight into who has the president's ear.

"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."

Among the frequent travelers is White House chief of staff Susie Wiles, who recently concluded treatment for breast cancer. Wiles, who co-managed Trump's 2024 campaign, has been called by Trump "the most powerful woman in the world."

Other key figures accompanying the president have included special envoy Steve Witkoff, who has been involved in diplomatic efforts concerning Iran; deputy chief of staff Stephen Miller, known for his role in shaping immigration policy; Housing and Urban Development Secretary Scott Turner; Treasury Secretary Scott Bessent; and Agriculture Secretary Brooke Rollins.

Commerce Secretary Howard Lutnick, a billionaire and long-time associate of Trump, has been a regular presence, often highlighting new factory investments as evidence of economic strength. Bill Pulte, director of the Federal Housing Finance Agency and a friend of Trump's, has also been on multiple trips. Pulte has previously been involved in policy discussions, including a proposal to extend the 30-year mortgage term.

Federal Communications Commission Chairman Brendan Carr has also flown with the president, using his regulatory authority to critique media coverage of Trump. Executive assistant Natalie Harp is a consistent presence on most trips, along with Walt Nauta, director of Oval Office Operations, and his deputy, Chamberlain Harris.

Speechwriting director Ross Worthington has repeatedly joined Trump on the plane, as has communications adviser Margo Martin and White House communications director Steven Cheung. Katie Zacharia, who briefly served as White House press secretary, accompanied the president on trips to Alaska, Nevada, Arizona, and Montana.

Strategic advisors on midterm efforts, such as political director Matt Brasseaux, have also been on board. Johnny DeStefano, a former top aide, rejoined the White House this summer to focus on midterm strategy and has traveled with Trump, as has former White House deputy chief of staff James Blair.

The president's entourage has also included notable figures from the boxing world, including Mike Tyson, Floyd Mayweather Jr., and Evander Holyfield. Retired NASCAR champion Richard Petty, former NFL coach Jon Gruden, and former NFL running back Todd Gurley have also made appearances at rallies, sometimes traveling with Trump.

Lawmakers traveling with the president have included House liaison Jeff Freeland, Representatives William Timmons, Beth Van Duyne, Brandon Gill, Brian Jack, Tim Moore, and Anna Paulina Luna. Senators John Barrasso and Ted Cruz have also flown with Trump on multiple occasions this month.