In a fascinating tale of indulgence and a company’s attempts to maintain control, a man found himself banned from flying after causing an airline to lose a staggering amount of money using his lifetime first-class ticket. Many would likely seize the opportunity to acquire such an extraordinary pass for a fraction of its actual value, where no more cramped seats, crying children, or endless queues would spoil their travel experience - truly, a dream come true!

Back in 1981, American Airlines introduced the AAirpass, a prepaid membership offering discounted flights to frequent flyers. For $250,000, passengers could purchase unlimited first-class travel for five years, or they could opt for an even pricier lifetime option that promised eternal luxury in the skies. However, the program didn’t take off as expected, with only 66 people purchasing the original AAirpass.

Rothstein tried to sue American Airlines in 2011 (Kevin Carter / Contributor / Getty)

One of the individuals who bought into the scheme was Steven Rothstein, a financier from Chicago. Rothstein gained notoriety for the lengths he went to in maximizing the deal. In 1987, he upgraded to the lifetime option, and two years later, he added the $150,000 'companion pass' that allowed him to bring a guest along on his travels. Over the years, Rothstein flew incessantly, becoming a well-known figure among flight crews.

As his daughter, Caroline Rothstein, stated in a news article, "A quarter of a million dollars gave him access to fly first class anywhere in the world on American for the rest of his life. He flew so much it paid for itself." Rothstein’s travel habits became legendary, but the airline’s finances couldn’t keep up with his constant flying.

'He flew so much it paid for itself' (Caroline Rothstein)

In 2008, during a period of financial instability, American Airlines launched a 'revenue integrity unit' to investigate whether the AAirpass program was a financial burden on the company. It was revealed that Rothstein, along with another member named Jacques Vroom, was costing the airline about $1 million annually. Without any prior notice, in December 2008, American Airlines terminated Rothstein's pass.

Rothstein was informed of this decision when he was allegedly stranded at Chicago O'Hare International Airport and handed a letter accusing him of 'fraudulent behavior.' However, Rothstein wasn't going to accept this decision quietly. He denied any fraud and attempted to take legal action against American Airlines in 2011. While the court sided with the airline, the case was privately settled in 2012.

In a 2019 interview with Forbes, Rothstein explained his side of the story. "They told me they viewed the AAirpass like a bond, so it was as if I was lending the airline money, and they needed money," he said. "So they gave me a very good deal." Rothstein also emphasized that he used his pass to help others. He shared, “I gave a man in Seattle a ticket to go to his father’s funeral. I gave many people tickets to visit ill family members. I don’t view that as philanthropy, I view that as good deeds."

After the dramatic fallout, Rothstein decided to cut ties with American Airlines for good and switched his allegiance to United Airlines, where he could continue to enjoy the perks of frequent flying without the baggage of a troubled past.