He used his pass to catch all of his son’s football games on the East Coast. Over the next 2 decades, Vroom flew an average of 2m miles per year. “But I took out a loan for 12% for 5 years and did it, because I thought it would give me a competitive advantage for life.” “I had never bought anything for $400k in my life,” he tells us.

Over in Texas, a direct marketing catalog consultant by the name of Jacques Vroom also decided to shell out the $400k for an AAirpass and companion pass. “The contract was truly unlimited,” he says. On occasion, he’d offer his companion pass to a complete stranger at the airport. He flew up to Ontario just for a sandwich. He went to London - sometimes a dozen times per month. He took hundreds of trips to NYC, LA, and SF. Rothstein)įor a total of $383k, Rothstein purchased both the AAirpass and companion pass - and over the next 25 years, he proceeded to book more than 10k flights. They needed cash, and they could pay me in miles.” Signatures on Steve Rothstein’s original AAirpass contract (via Mr.

“It was like a bond: instead of paying me dividends in cash, they were paying dividends in air travel. “American Airlines contacted me and said that, based on the amount I traveled, the AAirpass would be a great purchase,” Rothstein tells us. Steve Rothstein, then an investment banker in Chicago, was already one of American Airlines’ top fliers when he was approached to buy the AAirpass in the early ‘80s. People immediately figured out we’d made a mistake pricing-wise.”īy 1994, American had discontinued the unlimited AAirpass - but not before 28 people got the deal of a lifetime. “But as usual, the public is way smarter than any corporation. “The idea was that firms would buy this for their top performers,” Crandall tells us over the phone. So, they came up with a different plan: they’d raise capital from their own customer base by selling its wealthiest customers the “ultimate travel perk” - an unlimited first-class ticket for life. Robert Crandall (right) duels with former Southwest CEO, Herb Kelleher (via the Dallas Morning News)Īmerican needed cash, but interest rates were at a record-high. The airline’s newly-elected president, Robert Crandall, was on a mission to “cut American down to the bone” and lead a massive expansion from the ground up. They’d posted a $76m loss in 1980, and were grappling with new competition, reduced ticket prices, and a changing industry that threatened to sink them into irrelevancy. It was 1981, and American Airlines was in deep sh*t…Īmerican had been hit hard by the Airline Deregulation Act of 1978. Mark Cuban, an early AAirpasser, tells us it was “one of the best purchases ever made.”īut the unlimited AAirpass had a fatal flaw: it was such a good deal that it ended up costing American Airlines millions of dollars per year - and the company set out to revoke the contracts of its top customers by any means necessary. A companion pass could be purchased for an additional $150k, allowing the pass holder to bring along anyone for the ride. It was dubbed the “unlimited AAirpass.įor a one-time fee of $250k ($560k in 2018 dollars), this pass gave a buyer unlimited first-class travel for life. Three decades ago, 28 lucky bastards managed to snag the greatest travel deal in history, courtesy of American Airlines.

Airpass tickets