Man who cost airline $21,000,000 tried to sue them after he had his lifetime first class ticket removed while travelling

When taking to the skies, the first class experience is one that many of us aspire to enjoy but simply can't afford. So, you can imagine that people would jump at the chance to get a 'lifetime' first class ticket for just a fraction of the price it would cost to take all those flights.

This happened in the 1980s, with American Airlines' botched AAirpass and the now-infamous story of Steven Rothstein.

Although only 66 people shelled out the $250,000 for lifetime membership, it seemed like a lucrative deal to Rothstein, who then spent decades flying high at American Airlines' expense.

However, when the airline stopped Rothstein from boarding a flight with a friend in December 2008, he was shocked to learn American Airlines was revoking his supposedly 'lifetime' ticket. Apparently, his years of using the AAirpass had cost the airline a jaw-dropping $21 million.

Steven Rothstein was one of 66 people who bought the exclusive firstclass pass (Caroline Rothstein)

It didn't take long for a disgruntled Rothstein to mount legal proceedings against American Airlines, but who won the case?

Unfortunately for this one, the little guy didn't win.

American Airlines cited 'fraudulent behavior,' saying that Rothstein would approach fellow passengers at the gate and offer them a free upgrade to his companion seat (something he bought as a $150,000 add-on). He was also accused of purposefully keeping his companion seat empty and using it as a place to put his luggage while booking under a fake name.

Taking American Airlines to the United States District Court for the Northern District of Illinois, Rothstein's team argued: "American waived its rights to enforce the contract by not cracking down on Rothstein sooner." Having made the most of AAirpass for 21 years, it does feel like American Airlines was trying to close the gate after the horse had bolted.

The motion was denied in 2011, while litigation was delayed due to American Airlines filing for Chapter 11 bankruptcy. Both parties had settled out of court by the end of 2012, although Rothstein's appeal was dismissed and the airline's counterclaims dismissed with prejudice.

Another passenger, Jacques E. Vroom Jr. was also handed a letter similar to Rothstein (seng kui Lim/500px/Getty)

Rothstein wasn't the only one to face the wrath of American Airlines over the AAirpass, and in July 2008, Jacques E. Vroom Jr. was handed a letter similar to Rothstein. The airline tried to sue Vroom in 2011 and claimed that he was selling his companion seat, while Vroom countersued by arguing that the rule went into effect after he bought the ticket - as well accusing the airline of slander.

Vroom's case fell apart when American Airlines filed for bankruptcy and the claims went unresolved. Rothstein has since admitted that he was 'generous' with upgrading people he met on planes if they had a good story, and at the end of the day, thinks he got a pretty good deal from American Airlines.