Drunken Mark Cuban Made $125,000 Lifetime Flight Pass Purchase

Mark Cuban, the billionaire entrepreneur and star of “Shark Tank,” made a significant purchase shortly after selling his first company, MicroSolutions, to CompuServe for $6 million in 1990. During a recent interview on the “Club Shay Shay” podcast, Cuban revealed that he bought a lifetime flight pass from American Airlines for six figures while celebrating his newfound wealth.

Cuban’s decision to buy the pass came after a night of revelry with friends. When asked what he planned to do with his earnings, Cuban, who frequently traveled for work, expressed his lack of interest in cars or houses. Instead, he decided to invest in a lifetime of air travel. Despite being inebriated, he contacted American Airlines to inquire about a lifetime pass, which they confirmed was available.

The next day, nursing a hangover, Cuban signed up for the pass. The initial cost was $125,000, but he later upgraded it. The exact amount he paid for the upgrade remains unclear, but the pass provided him with nearly unlimited miles for himself and a companion for life.

The pass, known as the AAirpass, was introduced in the early 1980s. It offered buyers unlimited first-class travel for life, with the price determined by the buyer’s age at the time of purchase. Cuban was only 32 when he bought the pass, which would be equivalent to approximately $300,000 today, adjusted for inflation.

Cuban later transferred the pass to his father, and after his father’s death, he passed it on to a friend. Unfortunately, American Airlines no longer offers the unlimited pass. The airline discontinued the offer and began charging a flat rate for frequent business travelers. In 2022, they stopped accepting new Airpass memberships and renewals, and the program was officially closed in March 2024.

This wasn’t Cuban’s only extravagant purchase. In 1999, after selling his streaming platform Broadcast.com to Yahoo for $5.7 billion in stock, he bought a $40 million Gulfstream G5 jet online. This transaction is still listed on the Guinness World Records’ website as the “largest single e-commerce transaction.”

Despite his lavish spending, Cuban advises others, particularly athletes, to live frugally, like a “college student,” and save their money. He also maintains a modest lifestyle, living in the same house for 18 years and driving the same cars.