In 1990, a man named John Smith made what seemed like a brilliant deal of a lifetime. He purchased a “Gold Membership” from a luxury hotel chain for $100,000, which gave him free stays at any of their properties worldwide for the rest of his life. At the time, the hotel chain was looking for quick cash to fund a major expansion, and they introduced this offer, believing that most people would use it only a few times a year.

But John wasn’t most people. A retired businessman with a love for travel, he started using the membership in ways the hotel could never have imagined. He would spend months at a time in luxurious suites, hopping between properties in cities like Paris, Tokyo, and Dubai. His routine became legendary: New Year’s Eve in New York, summers on the Italian Riviera, and weekends at beachfront villas in Hawaii. John even began booking rooms for friends, hosting lavish gatherings at no extra cost.

Over the next two decades, he stayed in the hotel chain’s properties for over 7,500 nights. What the hotel thought would be a rare indulgence became John’s everyday life. The company estimated that his free stays cost them over $3 million, far exceeding the initial $100,000 he paid.

By the early 2000s, the hotel chain was facing financial difficulties, and John’s membership became a topic of heated internal discussions. They attempted to negotiate a buyout, offering him large sums of money to forfeit his lifetime membership, but John declined every time. He had gotten too used to his jet-set lifestyle.

Finally, in 2010, the hotel chain revoked John’s membership, citing “misuse of the benefits” and accusing him of violating the terms of the agreement by allowing others to stay under his name. John fought the decision in court, claiming that he had done nothing wrong, but the chain stood firm.

Despite the lawsuit, John’s legendary use of the “Gold Membership” became an enduring story in the world of luxury travel. What started as a bold financial move by the hotel had turned into one of the most costly mistakes in their history.