History of the Inverted Jenny, the First $2 Million Dollar United States Stamp

The Inverted Jenny has officially stamped its place in history.

The legendary stamp – aka the upside down airplane – has just made history after selling for $2 million at New York’s Robert A. Siegel Auction Gallery, the most ever paid for an individual United States stamp.

Printed in 1918, the Inverted Jenny is arguably the most iconic U.S. stamp ever and its record-setting history of sales is unprecedented in the philately (stamp collecting) community.

The stamp originally cost $0.24 per and was created to celebrate the United States Postal Services’ first year of regular airmail distribution. It depicted the Curtiss Jenny JN-4HM, colloquially known as the Jenny or the Mail Truck of the Skies.

Due to its multiple colors and a rushed timetable, the print sheets needed to be run twice, thus introducing the potential for errors.

Workers discovered at least three compromised sheets, but by then it was too late. The errors were out and the word spread fast.

Which led collector William T. Robey to procure a sheet from his local post office for just $24.

The philatelist immediately sent the sheet to Philadelphia stamp dealer Eugene Klein for an eye-popping $15,000. Klein, in turn, shipped it to Colonel Edward H.R. Green for $20,000. All told, the sheet was sold three times in less than seven days.

Klein and Green decided that splitting the sheet into individual stamps would help boost its value even further, so they were each numbered and sold off.

Time took out many of the stamps, with legend claiming that one of them was mistakenly used to mail a letter.

Green sold his remaining block of eight Inverted Jenny’s for $27,000 in 1944. That strip was then pared down to four stamps and sold for $18,000. Throughout the years it raised to $150,000 before joining the iconic Bill Gross collection in 2005 for $2.79 million.

Other versions have enjoyed a similar rocket in valuation. The Inverted Jenny Position 58 sold at Siegel in 2016 for $1.35 million, the most ever paid for a single stamp at the time.

That was before Siegel’s record-setting auction in November.

The $2 million version, referred to as “Position 49” is easily the highest graded Inverted Jenny there is and likely will be. Purchased in 1918 by a family, the stamp remained pristine in a vault for more than 100 years, before arriving for auction to wow philatelists worldwide.

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