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That wasn't before he'd flown with them 10,000 times though, racking up more than 10 million air miles in the process.
Steve Rothstein decided to use his powers for good, by making sure that people got home safely when they were stranded as well as flying a priest to Rome for an audience with the Pope, and even allowing a friend to visit the Louvre.
Other times, he used his ticket to benefit his family, but sometimes he just wanted to get to a baseball game, or have a particular sandwich.
Nowadays, there would be serious concerns about his carbon footprint - and he'd have to live 100 lifetimes to work that off, you'd imagine - but back in 1987 it wasn't something the average person was aware of.
Back then, Rothstein forked over the princely sum of $250,000 for his AAirpass, as well as a companion seat that cost $150,000.
In the end, he got around $21,000,000 worth of flying out of American Airlines, before they eventually cancelled his ticket because of supposedly fraudulent activity.
True, sometimes Steve would put made-up names like 'Bag Rothstein' on his ticket if he didn't know who he was travelling with, but he claims that AA have violated their contract.
In truth, American Airlines is currently trying to review the AAirpass program to get rid of a few of the 66 high-level contracts that are costing them millions every year.
Well, except for maybe last year, but that was different.
For his part, in 2012, Steve told The New York Post: "[I] became a hero at the airline."
He added: "I could just show up and get a seat.
"I could go someplace and I wouldn't even have to think about it.
"Just make the reservation and go."
That's exactly what he did. In July 2004 he travelled 18 times to various destinations around the world. He took an entire business junket to Caracas in Venezuela, and sent his daughter to a posh boarding school in Switzerland.
He'd even head to Rhode Island just to have a certain sandwich - a baloney and Swiss cheese melt - from a favourite shop.
However, that wasn't all he did.
He gave away all 14 million air miles that he accrued over the years, paying for a woman to get a flight back to New York because her children didn't have a sitter, and helping a friend get back to his native Bosnia.
He did those things because he 'felt those random acts of kindness were exactly the sorts of things that we're meant to do as people'.
But that's what eventually saw him caught out.
On that Bosnia excursion, he was told his pass had been terminated because of fraudulent activity.
Rothstein explained: "I feel betrayed.
"They took away my hobby and my life. They essentially destroyed my persona."
"Our country is almost captive to big companies who have incredible power to do whatever they want to do.
"It's hard to fight them."
He concluded: "They signed a contract, and a contract's a contract."
As far as we know, to this day, he hasn't managed to get his 'life' back. However, while it may be scant consolation, he definitely got his money's worth from it.
Needless to say, American Airlines no longer offers such a product.
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