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Everybody makes mistakes, and remember, corporations are people too, therefore they too make mistakes—Blockbuster

turned down the chance to buy Netflix, KFC opened in China and mistranslated, “it's

finger-licking good,” to, “eat your fingers off,” and American Airlines, well, American

Airlines sold the infamous unlimited lifetime…

Ahye-airpass?

Ah-Airpass?

Ay-yerpass?

You know what, let's just call it the airpass.

See, in the 1980s, American Airlines had a problem—they didn't have any money.

At the time, the airline crucially needed money as years of research, trial, and error

had concluded that the Pratt & Whitney JT3D, JT8D, and JT9D turbofan engines used in their

aircraft would not function without fuel… which costs money.

Now, people respond to not having money in all kinds of different ways.

Some file for bankruptcy, some steal a loaf of bread, some start a semi-satirical educational

YouTube channel—but American Airlines decided to respond with something truly drastic: offering

this unlimited lifetime AAirpass.

The idea was simple.

When the pass was first offered in 1981, it cost $250,000, and you could spend an additional

$150,000 for a companion pass.

So, if you bought both, you were looking at a total of $400,000—with inflation, today

that would be around $1.2 million.

In exchange, you got unlimited, free first-class travel to anywhere in the world, on any American

Airlines flight, for life and with the companion pass, you could take anyone you wanted with

you: it could be your friend, your spouse, your friend's spouse, a stranger, a stranger's

spouse, a stranger's friend's spouse, or Bill Clinton.

28 people took American Airlines up on the offer.

Now $400,000 may sound like a lot of money—especially for 1981—and to be fair, it was.

With inflation, it's enough to buy 138,771 Chipotle burritos with guac, or 32,875 years

of CuriosityStream, or to buy just under 0.9% of this weird drippy, swirly painting of nothing.

But even though $400,000 is a lot of money, soon American Airlines discovered that they

had made a terrible mistake in their pricing: they had offered people far too good of a

deal.

See, the unlimited passes were like an all-you-can-eat buffet.

All-you-can-eat buffets make money because even though people could eat 50 lamb chops

in one sitting, eating up all the buffet's money, the buffet assumes that nobody will

actually do that, because it would be… you know… gross.

American Airlines did the same thing—they assumed people wouldn't use the pass too

much, but they failed to consider the supertravelers: supertravelers like this guy, Steven Rothstein,

who did the flying equivalent of going to an all-you-can-eat buffet and eating fifty

lamb chops, eighty steaks, and an entire trashcan full of mashed potatoes.

Steven Rothstein, a Chicago investment banker, bought the unlimited Airpass in 1987.

Over the next 25 years, he would use his pass to book more than 10,000 flights.

That's an average of more than a flight a day.

He would fly to London to get lunch with a friend or to Boston for a baseball game, then

back home for dinner.

Sometimes he would fly to Providence, Rhode Island, just to get his favorite sandwich—a

bologna-and-swiss melt from a restaurant called Geoff's.

This meant that whenever Steven Rothstein got hungry, American Airlines had to pay hundreds

or thousands of dollars in fuel, taxes, and other costs—not to mention lost ticket sales—to

fly him to his bologna-and-Swiss melt—which is a lot of money, especially for a sandwich

with bologna, a meat so bad that its name literally means nonsense.

I mean come on, if you're gonna fly across the country, at least get salami?

And it wasn't just Rothstein—a lot of people used their passes much more than expected.

One pass-holder, Mike Joyce, once used his pass to fly round-trip to London 16 times—in

25 days.

Keep in mind, too, that back in the 80s, when the pass was first offered, flying cost a

lot more than it does now.

When you adjust for an inflation, the cost of flying is now about 50% less than it was

in 1980.

Soon, American Airlines realized they had made a terrible mistake.

They estimated that supertravelers like Rothstein were costing them over $1 million a year,

each, which made sense.

By 2008, Rothstein had traveled over 10 million miles or 16 million kilometers, enough to

go to the moon and back 20 times.

Now, of course, Rothstein didn't actually fly to the moon; but it turns out he had flown

too close to the sun—and he was about to get burned.

It turned out that Rothstein and others would often use their passes to help out complete

strangers, giving them unexpected first-class upgrades, or helping them get home when their

flights were cancelled.

That wouldn't normally be a problem—except that in order to have the option to do it,

the pass-holders would regularly book their companion pass seat under a fake name, as

they didn't yet know who might be traveling with them—silly, made-up names like Bag

Rothstein, or Benedict Cumberbatch, you know, names that no real human being would ever

have.

In 2008, American Airlines accused Rothstein and two others of fraud, and said by booking

under false names, they had broken their contract.

Security agents cornered them at airports, revoked their passes, and told them that they

would never fly on American Airlines again.

Just like any red-blooded American would, they all sued, but for Rothstein's case,

at least, the outcome wasn't clear as it was settled privately out-of-court.

American Airlines stopped regularly offering the unlimited lifetime pass in 1994, though

they did offer it once in 2004, for $3 million, plus $2 million for a companion pass—for

a total of $5 million, or $6.8 million today with inflation.

That time, though, there were no takers.

After all, with $5 million, you might as well just buy your own plane—or you could buy

7% of this other painting of this drippy swirly painting of nothing.

25 people, though, still have lifetime unlimited passes including Michael Dell, who you might

know from Dell computers, and Mark Cuban, who you might know from Shark Tank and yelling

at referees at Dallas Mavericks games.

They can still fly anywhere, anytime, first-class on any American Airlines flight and so long

as they don't break the rules, they can do it for the rest of their lives, but let's

hope they don't start craving too many bologna-and-swiss sandwiches, lest they meet Steven Rothstein's

same sad fate.

Who will never sell you a lifetime subscription, panic, and then take it away from you is Audible.

Don't tell them this, though, but Audible's, like, a really good deal.

They should probably panic.

You see, with a free trial, you can get an audiobook for $0.00.

That audiobook can be anything—even a 56 hour-long odyssey like Infinite Jest which

might not be the best choice.

I genuinely don't know because neither I not anyone has ever finished it —so I'll

actually recommend The Hitchhikers Guide to the Galaxy.

It's read by Stephen Fry and its one of these things where there's a reason you

keep hearing about it—because it's fantastic.

Audible is the place to get Audiobooks which, since you can listen whenever,

can make anything more entertaining, and, once again, by signing up at audible.com/hai

or texting hai to 500-500, you will get one audiobook plus two audible originals for free.