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Joining loyalty programs and racking up frequent flier miles for free flights and upgrades can be challenging. But if you know the game and stick with one or two airlines, it can really pay off with some solid perks and savings. While earning elite status is relatively common, buying a lifetime airline pass is pretty unheard of.

But that's precisely what happened back in 1990. A $125,000 splurge Mark Cuban recently reflected on a purchase he made over 30 years ago—a six-figure splurge that earned him a lifetime pass on American Airlines flights. Speaking on the "Club Shay Shay" podcast last week, the billionaire admitted, according to CNBC , that he made the purchase while hungover after selling his first company for $6 million.



Cuban said: "My buddies and I went out and just got destroyed. 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.'" The American Airlines lifetime pass cost Mark Cuban $125,000, but he later upgraded it.

It is worth noting that taking inflation into account, such a pass would cost $300,100 today. "I called them up and just slurred my words, ‘Do you guys sell lifetime passes?’ 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." Can you guess the order of them? .

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