What is it about the mind of a collector that makes it magnetically, perhaps even maniacally drawn to that which is considered rare? Whether the objects collected are records, dolls, paintings, books, toys or cars, the name of the game is getting your hands on that which is hard to come by.

From the outside, it appears that the collector has such a deep appreciation of the object that the acquisition of it fills what would otherwise be a void in mind, body and soul. I’ve come to realize, however, that in many cases, what is more valuable than the object itself, is the story that the holder of the object can tell.

Think about it. What do you do after you’ve acquired that one piece that you’ve always wanted in your collection? If you’re like me, with a seemingly insatiable desire for music, you swoon over it for a moment, perhaps give it a spin or two and then put it on the shelf with the other albums. But, by acquiring the piece, you’ve joined the club of people who have experienced, and can tell first-hand, the story of that piece. And that, in many instances, is more valuable than the piece itself. I’m thinking here about a rare record, a collectible trading card, or a numbered print; something that is cool to own, and perhaps a bit hard to come by, but not outrageously expensive.

Then there are the items that drive collectors crazy; those pieces whose monetary value goes so far beyond any satisfaction you could possibly glean from bragging rights, that it approaches the absurd: an un-pasted copy of the Beatles “Butcher Cover,” an Action Comics #1 in mint condition, or, the hero of our story: a little stamp with an upside down airplane on it, known affectionately as the Inverted Jenny.

In 1918, the U.S. Postal Service inaugurated its air service. To commemorate the historic event, they released a stamp with the image of a Curtiss Jenny—the bi-plane chosen to transport the mail—on it.

In a twist of fate, the little stamp that may well have gone on to the annals of postal obscurity, has instead inspired multi-million dollar deals, and solidified itself as one of the most famous images in the history of collecting, as a sheet of the commemorative stamps was printed and sold with the image of the plane inverted.

You have to look closely to spot the error, but once you do, it’s obvious that the plane is upside-down; an error that keeps auction-types on their toes, and poor collectors in what can only be a state of resignation, that the coveted piece will, most probably, never be theirs. Single Inverted Jennys regularly fetch nearly a million dollars at auction, and a block of four stamps sold, in 2005, for $2.7 million.

Back in the day, inverted stamps were not terribly uncommon. When two colors were used on a printing press, the paper—in this case a sheet of stamps—had to be fed through twice; once for each color. If you’ve ever tried to make double-sided copies of something, you know that getting it right can be an exercise in trial and error, and that you usually end up sending a couple of trials to the recycling bin. It’s kind of like that.

Printing errors happen. The throwaways are scrapped, and the intended prints are kept. The story of the Inverted Jenny, is that the printers caught their mistake early in the run, and destroyed at least three sheets. But one sheet slipped through, and was purchased, at his local post office, by a collector by the name of W.T. Robey, who, interestingly enough, had mentioned to another collector friend that he should be on the lookout for inverted stamps.

When Robey requested a sheet of the commemorative stamps and spotted the inverts, his “heart stood still” and he asked to see the other sheets, all of which had the intended, right-side-up design. The story gets a bit vague here, as Robey told a few different versions of it, but apparently the next week included contact with journalists, collectors, and the postal inspector, and the hiding of the now-famous sheet, before he sold it for $15,000 to someone who immediately flipped it for $20,000.

The third owner was advised that the stamps would be worth more split up than in a sheet, so a block of eight and several blocks of four were pulled out, and the rest of the stamps pieced off to collectors individually, thus furthering the allure of one of the great stories in postal (and printing) history.

What sets collectible, inverted stamps apart from their printer’s scrap pile counterparts is the fact that they were, at some point, sold to the public; an occurrence that holds a regular spot in postal lore. There are stories from around the world of mis-printed stamps that have slipped past the eye of the printer and out into the public, but none—from what this non-philatelist can tell—more famous than the Inverted Jenny.

This is the kind of tale that collectors live for. The stamp, in and of itself, would not even get your letter from here to there. The entire value of the Inverted Jenny is in its story, and what a great story it is. The question is: would you pay a million dollars to tell it?