Billionaire Mark Cuban once bought a $125K American Airlines lifetime pass on a whim after a night out

Mark Cuban once made one of the wildest impulse purchases in travel history: an American Airlines lifetime pass, also known as the AAirpass.

It was 1990, and the 32-year-old had just sold his first company, MicroSolutions, for $6 million.

While most new millionaires might splurge on cars or mansions, Cuban’s late-night decision was fueled by his love of flying.

And yes, he sealed the deal while still hungover from celebrating.

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You can’t get the American Airlines lifetime pass anymore

On the Club Shay Shay podcast hosted by former NFL player Shannon Sharpe, Cuban explained how it happened.

“My buddies and I went out and just got destroyed,” he said.

“They’re like, ‘What do you think you’re going to do with all this money?’ And I’m like, ‘I don’t care about cars or houses, but boy, you know, I fly a lot for work.’”

This seems pretty in-character for Cuban, given the fact that he paid a surprisingly tiny sum for his first car.

Half-drunk and half-joking, he called American Airlines and slurred:

“Do you guys sell lifetime passes?”

Turns out, they did.

For $125,000, which is roughly $300,000 in today’s dollars, Cuban scored the AAirpass, which granted him virtually unlimited first-class flights for life, plus a companion ticket.

He later upgraded the package for even more perks, though he admits he can’t remember the exact total cost.

Cuban made the most of his golden ticket, often inviting friends on spontaneous trips.

Suffice to say, like this other man who got his hands on the AAirpass, Cuban must have racked up plenty of miles.

Eventually, he transferred the pass to his dad, and later to a friend after his father’s death.

The AAirpass itself has since become legend.

Introduced in the 1980s, it was eventually replaced by Airpass in 1994, which offered fixed-rate flights instead of unlimited travel.

American stopped selling new memberships in 2022 and ended the unlimited perks entirely in March 2024.

In fact, an individual even got his American Airlines lifetime pass revoked by the airline after he cost the airline $21 million.

Mark Cuban values the time he saves from flying private

Of course, Cuban’s relationship with air travel didn’t end with American Airlines.

In 1999, after selling Broadcast.com to Yahoo for $5.7 billion in stock, he upgraded in the biggest way possible: a $40 million Gulfstream G5 jet.

That purchase still holds a Guinness World Record as the most expensive e-commerce transaction ever.

Reflecting on the splurge, Mark Cuban said in 2017 that buying a plane was always his ‘all-time goal’ because the asset he values most is time.

This makes a lot of sense, given that private jet flying is basically the most visible marker of real wealth.

Still, that spur-of-the-moment phone call in 1990 gave him plenty of flights before he got his hands on his private jet, and an awesome story for the rest of his life.

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