Who's on Air Force One? Trump's midterms entourage includes strategists, aides and aging athletes

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Cite

Boak, J. (2026, October 25). Who's on Air Force One? Trump's midterms entourage includes strategists, aides and aging athletes. Toronto Star. https://www.thestar.com/news/world/united-states/who-s-on-air-force-one-trump-s-midterms-entourage-includes-strategists-aides-and-aging-athletes/article_9ca2eb6e-a881-5bec-9879-28fef4c0144b.html

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Toronto Star · collected 2026-10-25 · by Josh Boak

Quick Summary

President Donald Trump has been using Air Force One extensively this month to travel across the United States for midterm election rallies, clocking about 70 hours in the air so far. The article details the diverse entourage accompanying him, including White House chief of staff Susie Wiles and other key figures like Steve Witkoff, Stephen Miller, Howard Lutnick, Bill Pulte, and Brendan Carr, highlighting their influence on Trump’s policy decisions and campaign messaging.
Written locally by qwen2.5:14b on 2026-10-25, using this article's own text rather than the other coverage of the same event (that is the story summary below).

AI analysis runs on qwen2.5:14b, locally

Story summary

As of October 25, 2026, President Donald Trump is spending approximately 70 hours aboard Air Force One to attend numerous rallies across the United States ahead of the midterm elections. This extensive travel includes a diverse entourage that ranges from Cabinet members and strategic aides to notable figures like aging athletes. Among these passengers are individuals with less public recognition but significant influence, such as Bill Pulte, who despite holding the title of director at the Federal Housing Finance Agency, has been seen on multiple legs of Trump's campaign tour, indicating his elevated status within the administration. Additionally, key figures like White House Chief of Staff Susie Wiles, recently recovered from breast cancer treatment and considered by Trump to be "the most powerful woman in the world," are frequent companions during these trips, highlighting their importance to the president’s decision-making process.

Written for “Trump's Midterms Entourage” on 2026-10-25, grounded in this article and the 0 other(s) covering the same event.
Why this leaning score
This article does not take a side on a contested political question, so it has no leaning score. That is an answer rather than a gap: a match report or a rescue can be warmly or critically written without being left or right, and scoring it anyway is how approval of a subject gets recorded as a political position.
No political leaning scored for article 106160 · logged 2026-10-25

Story

📰 Trump's Midterms Entourage
Politics · 1 article(s) covering the same event.

Compared with similar articles

Nothing to compare against. No article is close enough to this one for the pipeline to have linked or judged the pair.
How this article was measured signals, leaning charts, publisher record, byline, topics and claims

Signals How these are calculated →

Claims extracted
44
sentences that state something as happening or true
Uncertain
2%
1 of 44 hedged ("reportedly", "may", "according to")
Leaning
not political
takes no side on a contested political question
Publisher signals
64/100
Toronto Star's corrections and hedging, across everything collected from it. Not a measure of accuracy.
Outlets on this story
1
Politics
Same framing elsewhere
1
articles that frame the event the way this one does
Analyzed 2026-10-25 · how these are computed

How this is being covered How these are calculated →

Article leaning vs. publisher reliability
Source leaning vs. consistency

Publisher

Toronto Star · 9798 article(s) · 26 correction(s) detected
Running correction rate · 26 correction(s)
2026-10-24
Correction
2026-10-07
Correction
2026-09-24
Correction

Who wrote this

Josh Boak
12 article(s) here · 1 carrying a prediction
🔮 Punching above their weight 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.
🔮 PERRY, Ga. (AP) — President Donald Trump on Saturday announced that Audi will build an automobile plant in Georgia as he tries to deliver on his promise to bolster American manufacturing in the final days before the midterm elections.
🔮 President Donald Trump on Friday told a rally for candidates in South Florida that U.S. warships returning from the Middle East could stop over in Cuba on their way back from the Iran war, his latest suggestion of taking an interventionist approach to the nearby country.
🔮 In his inaugural address last year, the Republican pledged: “I will direct all members of my Cabinet to marshal the vast powers at their disposal to defeat what was record inflation and rapidly bring down costs and prices.”
🔮 The outcome will be decided in places like Dayton, which once sprouted factories because it led America in patents per capita.
🔮 Ohio Republican Party Chairman Alex Triantafilou recently told The Associated Press that he hoped Trump would visit his state, where he won by 11 percentage points in 2024.
🔮 The biggest policy announcement of the visit was modest: an agreement to extend by two months a trade truce that had been set to expire in November.
🔮 That tough talk helped Trump get to the White House a decade ago, but since then, he increasingly speaks in glowing terms about Chinese President Xi Jinping, the geopolitical rival Trump will fete on Thursday with a state dinner.
🔮 Vance will be the headliner Friday at a midterm rally in Council Bluffs, on the western edge of the once-Republican stronghold state, which has found itself with competitive races for the Senate and the governor’s mansion this year.
🔮 President Donald Trump said Monday that he would be a sufficient guardrail against rogue artificial intelligence, claiming that any efforts to limit the technology was part of a “SICK conspiracy.”
Also by Josh Boak
Nothing else under this byline is closely related to this article, so these are simply their most recent.
All 12 articles by Josh Boak →

Topics

AIR FORCE ONE Cabinet Republican Party the United States the University of Akron

Subjects

Trump PERSON · 15× Cabinet ORG · 2× Pulte PERSON · 2× Republicans NORP · 2× Wiles PERSON · 2× the United States GPE · 2× David Cohen PERSON · 1× Donald Trump PERSON · 1× Republican Party ORG · 1× the University of Akron ORG · 1×

Narrative

Punching above their weight 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.
framing: assertive · carried by 1 article(s) · first seen 2026-10-25
🔮 Punching above their weight 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.

Claims (44 extracted, 1 hedged)

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. asserted
Trump → clock → 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. asserted
who → range → words
The passenger list for Trump’s marathon through the sky signals who has the ear of the president. asserted
who → signal → president
“It can say what his priorities are,” said David Cohen, a professor of political science at the University of Akron. asserted
Cohen → say → Akron
“Who he surrounds himself with are the people he is going to be listening to. asserted
he → surround → himself
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. asserted
who → ’re → States
Here’s a look at who has had access to power in the confines of Trump’s plane this month. asserted
who → ’ → plane
The inner circle White House chief of staff Susie Wiles, who recently finished treatment for breast cancer, is a frequent flyer. asserted
who → finish → cancer
Trump has called Wiles, who co-managed his 2024 campaign, the “most powerful woman in the world.” asserted
who → call → 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. asserted
she → ascend → aisle
“Great,” she said. asserted
she → say → ?
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. asserted
that → make → crackdown
The most frequent Cabinet member aboard has been Commerce Secretary Howard Lutnick, a billionaire who previously ran the financial services firm Cantor Fitzgerald. asserted
who → run → firm
A Trump buddy going back to the 1990s, Lutnick can often be heard laughing at the president’s jokes. asserted
Lutnick → go → 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. asserted
economy → highlight → supporters
Punching above their weight 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. asserted
who → punch → office
He has led pressure campaigns on Federal Reserve officials such as Jerome Powell and Lisa Cook. asserted
He → lead → Powell
Pulte has also passed along policy ideas such as changing the 30-year mortgage to 50 years, an idea that has since been abandoned. asserted
that → pass → idea
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. asserted
Carr → fly → swing
Carr has sought to use his regulatory powers over broadcast networks to chastise them over their coverage of the president. asserted
Carr → seek → president
Personal aides who keep Trump going Chief among the retinue of assistants around the president is Natalie Harp, an executive assistant who is on most of Trump’s trips. asserted
who → keep → trips
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. asserted
She → serve → ballroom
Although Trump likes to ad-lib, the speechwriting director, Ross Worthington, has joined him repeatedly on the plane this month. asserted
director → like → plane
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. asserted
Republicans → feature → election
He also tends to highlight new factory projects and investments in the communities he visits. asserted
he → tend → communities
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. asserted
Cheung → post → tour
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. asserted
who → spend → Alaska
Plenty of political strategists 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. asserted
who → surround → 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. asserted
Blair → rejoin → staff
Celebrities hitch a ride asserted
Celebrities → hitch → ride
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. uncertain
Trump → go → boxing
In a 1997 heavyweight championship bout, Tyson bit off a piece of Holyfield’s right ear. asserted
Tyson → bite → ear
They did not fly on Air Force One at the same time. asserted
They → fly → 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. asserted
work → say → environment
“You want to have people around you that make you feel comfortable,” Kumar said. asserted
Kumar → want → you
“When you think about it, it is really stressful. asserted
it → think → it
You want some relief.” asserted
You → want → relief
Who else has hitched a ride with Trump? asserted
Who → hitch → 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. asserted
Petty → go → Georgia
Influencer-turned-boxer Jake Paul also traveled with the president. asserted
Paul → turn → president
…and 4 more, not listed.
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