Mark Cuban Drunkenly Buys Lifetime American Airlines Pass

In 1990, entrepreneur and investor Mark Cuban made a legendary purchase that would set the course for countless flights to come—a lifetime flight pass from American Airlines.

At the age of 32, Cuban had just hit the jackpot by selling his software startup, MicroSolutions, to CompuServe for a cool $6 million. Flush with cash and celebrating with friends, he decided to invest in something that aligned with his frequent travel needs.

During an appearance on the “Club Shay Shay” podcast, Cuban recounted the moment that led to his impulsive purchase. “My buddies and I went out and just got destroyed,” he said, reflecting on the celebration. When friends questioned him about what he planned to do with his newfound wealth, Cuban replied, “I don’t care about cars or houses, but boy, you know, I fly a lot for work.”

In a bold and somewhat drunken move, Cuban picked up a corded phone—a nostalgic reminder of the pre-cellphone era—and dialed American Airlines, hoping to inquire about a lifetime flight pass. “I called them up and just slurred my words, ‘Do you guys sell lifetime passes?’” Cuban recalled. To his surprise, he was transferred to the AAirpass department, where he discovered that such a product did indeed exist.

While the exact amount he paid has been lost to time, Cuban revealed that it was around $125,000. The pass granted him and a companion nearly unlimited first-class travel for life. Cuban later joked, “And then I upgraded it,” hinting at the additional perks he secured for his travels.

American Airlines had initially introduced the AAirpass in 1981, providing unlimited first-class travel for members. Back then, the pass was available for $250,000, but by 1993, the price skyrocketed to $1 million.

Despite offering fixed-rate flights for frequent fliers in later years, the AAirpass program ultimately came to an end in 2022. However, those with existing contracts can still use their passes until they expire.