The ‘Inverted Jenny’: The story behind the mythical stamp that sold at auction for more than $2 million

Dubbed the “most famous postage stamp in American history”, the century-old ‘Inverted Jenny’ is so sought-after by collectors that one particularly well-preserved specimen recently sold for over $2m.

“The holy grail of postage”

Printed for the opening of the U.S.’s air mail routes in 1918, the red, white and blue stamp features an image of the first airplane used by the country’s postal service: the Curtiss JN-4H, a single-engine biplane nicknamed the ‘Jenny’.

While most of the 24-cent ‘Jenny’ stamps rolled off the press with the plane correctly depicted, a small number were accidentally printed with the JN-4H flying upside-down - hence the name ‘Inverted Jenny’.

The error affected a single sheet of 100 ‘Jennys’, which was bought at face value on the day the stamps became available for purchase. Right away, the sheet was then sold to a collector, before being broken up into singles and blocks.

And in recent years, more than one of these ultra-rare stamps has fetched a seven-figure sum at auction.

Most notably, a single ‘Inverted Jenny’ was bought for $2.006m in November 2023, by a collector who described the stamp as “the holy grail of postage” in an interview with The Washington Post.

The fee is a record outlay for a U.S. stamp. According to the New York auction house that oversaw the sale, this reflects the fact that the ‘Inverted Jenny’ in question is the “finest” known example of the stamp.

“The best that any Jenny will ever get”

Given a preservation rating of 95 out of 100, the stamp is in such good condition that it is a “virtual impossibility” that a better specimen will ever be found, Siegel Auction Galleries said in a statement.

Speaking to NPR, Siegel president Scott Trepel explained: “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.”

He concluded: “This 95 is the best that any Jenny will ever get.”

Trepel also stressed that the printing error on the stamp is understandable, given that airplanes remained a recent invention in 1918.

Indeed, only a decade and a half had passed since the the Wright brothers had pulled off the first powered flight of a heavier-than-air aircraft in 1903.

“People weren’t familiar with what [airplanes] looked like, and so the inverted plane on the stamp slipped through the inspectors, slipped through the clerk at the post office,” Trepel explained.

“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.’”

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