Have you heard of Steve Rothstein? This guy has one of the wildest stories in aviation history, and it’s completely real.

In 1987, Steve Rothstein paid $250,000 for something that no one would believe possible today: a lifetime unlimited flight pass with American Airlines. He also snagged a second pass for companions for $150,000. Sounds crazy? Wait, it gets even better.

Over the next 21 years, Steve Rothstein used this pass like no other. The man booked over 10,000 flights. Not per year — in total! Some days he flew twice in a row. Sometimes just for lunch in another state and back the same day. He traveled approximately 30 million miles, which is nearly 45 million kilometers. American Airlines paid over $21 million for these adventures.

What do you do with such a pass? Steve Rothstein was generous: he took homeless people to see their families, sometimes booked seats for companions who never showed up. He was simultaneously the most eccentric and the most expensive passenger the airline ever had.

In 2008, the company had enough. American Airlines sued Steve Rothstein and demanded the cancellation of his ticket due to alleged abuse. But here’s the twist: a contract is a contract. The courts sided with Steve Rothstein. He won.

Today, fewer than 20 people in the world hold such a lifetime pass. Steve Rothstein has long become a legend — not just as a frequent flyer, but as the living example of how a small clause in a contract can open the whole world to you. A golden ticket that truly paid off.