American Airlines' Unlimited Lifetime First-Class Pass (1981–2008)
Steven Rothstein flew 30 million miles for free. American Airlines flew into a $21 million hole. Only one of them saw it coming.
In 1987, Chicago businessman Steven Rothstein paid American Airlines $250,000 for an AAirpass: unlimited first-class travel, for life. He later paid another $150,000 to add an unlimited companion pass, so a second seat would always fly free beside him.
He used it. Over the following two decades, Rothstein logged roughly 30 million miles across some 10,000 flights, all free, all first class.
In December 2008, his passport was confiscated at Chicago O'Hare and his pass was pulled. American Airlines alleged Rothstein had been making speculative, often same-day bookings for flights he had no intention of taking, and had at times booked seats under names like "Bag Rothstein" and "Steven Rothstein Jr." The airline said the pattern of use had cost it roughly $21 million.
Rothstein sued for $7 million; American Airlines countersued for breach of contract. Neither case reached a verdict — the two sides settled out of court in 2012, on confidential terms. What is public is simpler: the pass never flew again.
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