'He Had No Idea'—For $125,000, Mark Cuban Could Remove Anyone From A Flight. Magic Johnson Found Out The Hard Way

Mark Cuban is known for his business acumen, but one of his best deals had nothing to do with tech or startups. In his late 20s, he made a move that let him fly first-class for free—whenever he wanted, for life. The cost? Just $125,000.

Back in the 1980s, American Airlines introduced an all-you-can-fly lifetime Airpass. It sounded like a great idea at the time, but the airline later realized it was a financial disaster. Cuban, however, made the most of it, hopping on flights at a moment's notice. The best (or worst) part? If a flight was full, the airline had to bump another passenger to make room for him and his guest.

One of those unlucky passengers? Basketball legend Magic Johnson.

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Cuban shared the story during a 2013 interview on The Howard Stern Show. After selling his first company, MicroSolutions, for $6 million, he celebrated by buying the Airpass on a whim. He used it to live a life of pure spontaneity. "I would walk into clubs, and I’d be, you know, talking to some girl, and I’m like, let’s just go to Vegas. I was having fun,'" he recalled. One time, he even jetted off to Barcelona for his 30th birthday just because a friend suggested it. No planning, no tickets in advance – just walking into the airport and flying away.

Then came the infamous Magic Johnson incident. On one flight, American Airlines had to bump someone to accommodate Cuban and his companion. That someone turned out to be Magic. Johnson never knew why he got kicked off, and Cuban later admitted that when he told him about it, Magic didn't even remember.

Cuban later transferred the pass to his dad, but for years, it was his golden ticket to a jet-setting lifestyle.

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Cuban Today: A Billionaire With a Lesson in Responsibility

While Cuban once lived on impulse and last-minute flights, he's a lot more grounded these days. He made his real fortune in the late ‘90s when he and his business partner, Todd Wagner, launched Broadcast.com, an early streaming service. Yahoo bought it for $5.7 billion in stock in 1999, making Cuban a billionaire overnight.

But despite his massive wealth, Cuban has worked hard to keep his kids from growing up entitled. In a 2023 interview with podcaster Bobbi Althoff, he opened up about how his children struggle with the expectations that come with being his kids. "Sometimes I think [the money] is the part they don't like," he said. "Not that they want to be poor, but it sets an expectation. It’s how other people see them."

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Cuban believes in self-reliance and has made sure his kids understand the value of money. He doesn't hand them blank checks or let them buy whatever they want. "You don't just get a credit card," he said in a 2020 interview. "I tell them, ‘After your health, my No. 1 thing for you all is, I don't want you to be entitled jerks.'"

He encourages them to earn their own success, just like he did. Cuban started out selling garbage bags door-to-door to save money for sneakers, and now one of his kids is following in his footsteps—selling candy bars at school to learn the basics of business.

Disclaimer: Some elements of this story were previously reported by Benzinga and it has been updated.

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