In 1987, a man purchased a lifetime unlimited first-class American Airlines ticket for $250,000. Over the years, he took more than 10,000 flights, reportedly costing the airline around $21 million. The ticket was eventually revoked in 2008. In 1987, Chicago stockbroker Steve Rothstein purchased American Airlines’ “AAirpass” for $250,000, granting him unlimited lifetime first-class travel. Over the next two decades, he used it more than 10,000 times, accumulating over 30 million frequent flyer miles and reportedly costing the airline around $21 million. He became known for treating first-class cabins as a personal transit system, taking spontaneous international trips just for lunch or to attend baseball games. The pass ultimately turned a promotional offer into a major financial liability for the airline. In December 2008, American Airlines revoked the pass at Chicago O’Hare International Airport following an internal investigation into its highest-cost users. The airline argued Rothstein had breached the agreement, citing actions such as booking companion seats under fake names like “Bag Rothstein” to keep adjacent seats empty and gifting flights to strangers. He later filed a breach-of-contract lawsuit to recover the pass, but the case was ultimately dismissed.(Historic Vids)