Mark Cuban dishes on his best drunk American Airlines purchase

Saturday, 5 October 2024

Mark Cuban dishes on his best drunk American Airlines purchase

by BD Banks

Aviation fans and longtime travel junkies will remember the brief stretch in airline history when there was a truly unlimited all-you-can-fly pass.

In 1981, American Airlines (AAL) launched an AAPass that let customers pay $250,000 and fly for free as well as access Admirals Lounges for years. The broad nature of the rules were, for the few who had the free time and could shell out that much money in one go, open to being milked for all its worth.

The most famous case is of investment banker Steven Rothstein buying it in 1987 and spending the next 25 years using it for nonstop travel (American Airlines eventually cut him off in 2008 long after phasing out the pass in 1994.)

Another person who had the chance to snap up the AAPass back when American Airlines was still selling it is investor and “Shark Tank” personality Mark Cuban.

Cuban in 1990: ‘You know, I fly a lot for work’

As he explained to former NFL tight end Shannon Sharpe on his “Club Shay Shay” podcast, Cuban was celebrating the sale of his first company MicroSolutions to software giant CompuServe for $6 million by getting drunk with friends.

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“They’re like, ‘What do you think you’re going to do with all this money?’” Cuban described to Sharpe. “And I’m like, ‘I don’t care about cars or houses, but boy, you know, I fly a lot for work.’”

Cuban, who was 32 at the time, said he paid $125,000 for a basic version of the pass and later upgraded it. Some passes were available for five years while others were for a lifetime subscription but Cuban admitted that he has forgotten the exact conditions all these years later.

‘I got all that information hungover as hell and I signed up’

“I called them up and just slurred my words, ‘Do you guys sell lifetime passes?’” Cuban continued. “I got all that information, hungover as hell, and I signed up. 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.”

Until the AAPass was discontinued in 1994 and those who had it used it until the remaining validity expired (Rothstein being a notable exception who slipped under the cracks), Cuban used it quite frequently.

“I’d be like ‘Want to go on a road trip? Let’s call American Airlines and see if they got any flights tonight,’” he described further on the podcast.

A professed plane junkie, Cuban did not miss out on the end of the pass as his career and prominence as an investor skyrocketed. Today, he owns three private jets — a Gulfstream G550 and Boeings 767 and 757 (BA) . The latter is customized for the Dallas Mavericks NBA team, of which Cuban is minority owner, while others are also chartered out to various corporate clients.

The $40 million purchase of the Gulfstream G550 also earned Cuban a spot in the Guinness Book Of World Records for the largest internet sale at the time (this was in 1999 and much biggest purchases have taken place online since then).