Mark Cuban Drunkenly Bought Lifetime American Airlines Flight Pass
Mark Cuban’s first significant payday came with an equally significant splurge. The billionaire entrepreneur once bought a lifetime flight pass from American Airlines, and the story behind this extravagant purchase is as entertaining as it is surprising.
Back in 1990, Cuban had just sold his first company, MicroSolutions, a software startup, to CompuServe for $6 million. To celebrate this major milestone, the newly wealthy Cuban decided to enjoy a wild night out with friends. During the festivities, a question arose about how he intended to spend his new fortune.
“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,'” Cuban recalled.
In a state of inebriation, Cuban made a bold decision that few could even contemplate. He called American Airlines, slurring his words, inquiring about the possibility of a lifetime pass. To his amazement, the offer was indeed available. This unique AAirpass, introduced in the early 1980s, granted holders unlimited first-class travel for life. The cost was determined by the purchaser’s age at the time of buying.
“I got all that information, hungover as hell, and I signed up,” Cuban shared. “Initially, it was $125,000, and then I upgraded it. I forget how much I paid, but it gave me almost unlimited miles for me and somebody else for the rest of my life.”
At just 32 years old, Cuban was in the prime position to seize this golden opportunity. Although it cost him $125,000 back then, it’s a sum estimated to be around $300,000 today, when adjusted for inflation.
The flight pass didn’t solely benefit Cuban. After enjoying the privilege himself, he eventually transferred the AAirpass to his father. Following his father’s passing, Cuban transferred the pass to a friend, ensuring that others could share in the luxurious experience.
Unfortunately, such lavish benefits from American Airlines are no longer on offer. The airline later discontinued this unlimited pass, transitioning to a flat rate for frequent business travelers. The Airpass program itself stopped accepting new memberships and renewals in 2022 and ultimately closed in March 2024.
This legendary flying pass wasn’t the only significant purchase Cuban made. In 1999, after selling his streaming platform Broadcast.com to Yahoo for $5.7 billion in stock, he made headlines again. This time, he bought a $40 million Gulfstream G5 jet online, a purchase that the Guinness World Records still recognizes as the “largest single e-commerce transaction.”
Despite his tendency to spend massively, Cuban is known for promoting financial responsibility. On the same podcast where he shared his flight pass story, he advised listeners to live like a “college student” and save money, especially athletes, who risk losing income if they become injured.
In 2017, Cuban exemplified his grounded lifestyle during an interview. He shared that despite having immense wealth, he maintained a modest lifestyle, living in the same house for 18 years and driving the same cars. Mark Cuban’s unique financial decisions reflect not just an adventurous spirit but a balance between enjoying wealth and living sensibly.
