If you think flying private or charter means you’re immune to travel delays, think again. The New York Yankees learned that lesson this week while traveling to Florida for their American League Division Series against the Tampa Bay Rays.
According to the Associated Press, the Yankees arrived at Westchester County Airport (HPN), just north of New York City, around 2:30 p.m. Thursday expecting to hop aboard their Delta charter and be in Tampa in time for dinner. Instead, a hydraulic problem with the aircraft turned what should have been an easy travel day into an ordeal.
@ShaunMorash Yankees charter was supposed to leave from White Plains but was cancelled and switched to LGA pic.twitter.com/FxT9xYuq6c
— Dan Greenstein (@dg12x) October 2, 2026
And here’s the part that every frequent traveler will appreciate: The problem apparently couldn’t be fixed because they couldn’t find a ladder tall enough. “Hydraulics issue. Didn’t have a tall enough ladder to fix it,” Yankees manager Aaron Boone told reporters. He then joked, “I offered to go get my ladder at home. Declined.” You can’t make this stuff up.
Players and staff spent hours sitting aboard the plane waiting for a solution. Eventually, they gave up on the original aircraft, boarded buses and drove 29 miles to LaGuardia Airport in Queens. Their replacement charter didn’t depart until around 10 p.m., and the team didn’t get to its Tampa hotel until around 1 a.m.
Yankees play-by-play announcer Dave Sims was traveling with the team and shared the play-by-play of his very long travel day on X. According to Sims, he boarded the plane at Westchester County Airport at 3:30 p.m., finally took off from LaGuardia at 9:35 p.m. and didn’t get into his Tampa hotel room until 12:38 a.m. As Sims put it, “Got in safely, albeit late. All good.”
Okay, I know, I know, it’s a First World problem, but I wanted to let ya see this…about my trip with the Yankees to Tampa on Thursday.
Out of bed 11:13
Lyft to Yankee Stadium 1:08
Arrive at Yankee Stadium 1:32
Bus to Westchester Airport 2:17
Arrive at Westchester Airport…
— Dave Sims (@davesims_) October 2, 2026
Gerrit Cole, who is scheduled to start Game 1 against Tampa Bay, summed up the journey perfectly: “We drove further away from Tampa and then we worked our way closer back to Tampa, and then we flew to Tampa.”
So what do multimillionaire professional athletes do when they’re stuck on a broken airplane? Pretty much the same things the rest of us do.
Cole said they passed the time playing cards, talking, teasing each other, playing video games and “doom scrolling.” Some players watched baseball and football while several pitchers reportedly broke out a Nintendo Switch and played Rocket League and Mario Kart. Their planned dinner in Tampa ended up being pizzas delivered to the tarmac at LaGuardia.
There’s a good travel lesson in all of this. I’ve been traveling professionally for three decades and one thing I’ve learned is that it doesn’t matter if you’re sitting in economy, first class or flying on a private or chartered jet. Travel is unpredictable.
Planes have mechanical problems. Weather rolls in. Air traffic control issues pop up. Flights get delayed or canceled. Bags get lost. Roads to airports get jammed. Sometimes there’s simply no ladder tall enough.
Obviously, some travelers have far more comfortable options than others when things go wrong, but no amount of money or status can completely insulate you from travel headaches.
What you can control is how you react to them. Aaron Boone seemed to understand that. He told reporters that everyone handled the situation well and later described their ordeal as “first-world problems,” noting that people have to deal with much worse things. That’s pretty much my travel philosophy, too.
I try to go with the flow because getting angry usually isn’t going to make the plane take off any faster. And whenever I start getting frustrated, I try to remind myself how fortunate I am to be traveling in the first place.
We’re also living in an incredible era for dealing with delays. We have smartphones, high-speed internet, streaming movies, live sports, video games, food delivery, airline apps and countless other ways to stay entertained, informed and connected while we’re stuck. Just make sure your devices are fully charged and carry a portable battery charger so you can recharge if you can’t find a power outlet.
I’m especially grateful when I’m traveling with my family. As long as I’m with them, it really doesn’t matter whether we’re sitting on a beach in Hawaii or stuck on the tarmac at LAX.
Though, for the record, I’ll take the beach in Hawaii.
