A Man Bought a $250,000 Lifetime Flight Pass. It Cost American Airlines $21 Million.

In 1981, American Airlines had a cash flow problem. Their solution: sell lifetime unlimited first-class passes for $250,000 each. They called it the AAirpass. It seemed like easy money.

Enter Steven Rothstein

Chicago financier Steven Rothstein bought one in 1987, plus a $150,000 companion pass that let him bring a guest on every flight. Total investment: $400,000.

Then he started flying. And flying. And flying.

Breakfast in London. Lunch in Paris. Dinner in Tokyo. Weekend trips across the country on a whim. He accumulated over 30 million frequent flyer miles and took more than 10,000 flights.

"Bag Rothstein"

American Airlines estimates Rothstein cost them over $21 million. When they investigated, they alleged he'd been booking phantom companions to keep adjacent seats empty. One recurring name on the companion list: "Bag Rothstein."

The Termination Letter at the Gate

In December 2008, Rothstein checked in at O'Hare Airport for a flight to Bosnia. An airline agent walked up and hand-delivered a letter: his pass was permanently revoked.

The two sides eventually settled out of court. American Airlines discontinued the AAirpass program entirely, estimating the roughly 66 passes they'd sold had cost the airline more than $100 million combined.

A $250,000 marketing gimmick turned into one of the most expensive mistakes in aviation history.