Imagine flying anywhere in the world for free, anytime you want, and taking someone with you. Sounds like a dream, right? This dream became a reality for Mark Cuban when he purchased an American Airlines lifetime Airpass for $125,000 at just 29 years old.
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The pass allowed him and a companion to fly first-class anywhere, anytime, for life. But that's not all – if the flight were full, someone else would have to be removed to accommodate Cuban. One day, that "someone else" happened to be basketball legend Magic Johnson.
Cuban shared the unbelievable story in a 2013 interview on The Howard Stern Show. He lived a high life after selling his first company, MicroSolutions, for $6 million. He had just purchased the Airpass on a whim after a night of celebration. This pass was a golden key to spontaneity for Cuban: “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.”
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He also recalled how he once casually decided to go to Barcelona for his 30th birthday just because a friend suggested it. There was no planning, no booking – just walking up to the airport and flying away.
During one flight, the airline needed to make room for Cuban and his companion, and the unlucky person booted off the plane was none other than Magic Johnson. According to Cuban, Johnson had no idea why he was being bumped and likely didn’t realize it was because of Cuban's Airpass– “I’ve said it to him, but he doesn’t remember,” Cuban reflected later when talking to Johnson.
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Although American Airlines eventually realized selling these passes was a financial disaster and discontinued the program, Cuban's lifetime pass, which he later transferred to his dad, is a testament to the crazy, once-in-a-lifetime deals that were possible back then.
Today, with rising fuel costs and tightened airline budgets, the idea of such a pass seems almost too good to be true. But for Cuban, it was a reality that paid off in unforgettable experiences – and some very awkward moments for Magic Johnson.
Mark Cuban wasn't just savvy in the skies; he was also a trailblazer in the digital world. In the late 1990s, he and his business partner, Todd Wagner, founded Broadcast.com, a company that pioneered online streaming long before it became the norm. Their foresight paid off handsomely when Yahoo acquired Broadcast.com for an astounding $5.7 billion in stock in 1999, instantly making Cuban a billionaire.
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