Why a single 'Inverted Jenny' stamp sold for $2 million at auction

By Manuela López Restrepo

Published November 20, 2023 at 2:59 PM CST

An enlarged replica of a block of four rare United States airmail error stamps, known as the Inverted Jenny plate block.

History, intrigue and a misprint combine so that a single stamp has sold for $2 million at auction.

What is it? Well, at the basic level, it is a U.S. postage stamp from 1918. But this stamp's got lore, baby.

The design — which normally shows the "Jenny" Curtiss biplane the right way up — was already important because it was used on the stamps for the world's first regularly-scheduled government airmail service.
What makes this particular stamp noteworthy is that in the glory-induced rush of stamp making at the time, the workers who were printing this sheet accidentally placed the Jenny upside down.
The single sheet of 100 so-called "Inverted Jennys" was sold before anyone caught the mistake, and they have become treasured collector items ever since.

So it's a big deal? It is the "icon of stamp collecting," according to Scott Trepel, the president of Siegel Auction Galleries in New York and an expert in the stamp field.

He says to keep in mind that planes weren't particularly common in 1918: "People weren't familiar with what they looked like, and so the inverted plane on the stamp slipped through the inspectors, slipped through the clerk at the post office. And even he said, you know, 'Look, don't blame me. I don't know what a plane looks like, so I didn't recognize it when I sold it.'"
Trepel says this one is extra special because it's in really good condition after being in storage for decades: "It never was exposed to light. The colors were beautiful. The paper was bright. The back of the stamp, the gum had never been hinged and put into an album."

Want more on history? Listen to Consider This on the uniquely American tradition of hot dog eating contests.

So, what now?

While there are still other inverted Jenny stamps floating out there (one was stolen in the 1950s and has yet to resurface), Trepel says that this recently-sold one, named "Position 49" for its place on the original sheet of 100, is the cream of the crop.
"We grade stamps from one to 100 in terms of the centering of the design with the perforations around it. And this one is a 95, and there is no better. There's no 98. There's no 100. This 95 is the best that any Jenny will ever get."
And if this story has given you FOMS (Fear Of Missing Stamps), there are some delightful Strega Nona-themed ones available for just 66 cents a pop.

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The radio version of this story was produced by Gabriel J. Sánchez, Kat Lonsdorf and William Troop, and reported by Ari Shapiro and Ailsa Chang. contributed to this story