A Rare “Inverted Jenny” Fetches a Record-Breaking $2M at Auction

Sought after by the wealthiest of stamp enthusiasts, these misprints drive million-dollar sales and were the subject of a notable 1955 heist.

Stamps from a specific 1918 batch run have, for more than a century, been considered the holy grail of stamp collecting among affluent philatelists. Earlier this week, one of these misprints, known as “Inverted Jennies,” became the most valuable U.S. stamp to ever come to market when it fetched a record-breaking $2 million at auction.

Square stamp with red border and blue plane pictured upside down
The stamp in question is known as the finest example of the Inverted Jenny. Courtesy Siegel Auction Galleries

Depicting a Curtis JN-4H “Jenny” biplane, the 24-cent stamp was designed by Clair Aubrey Huston to honor the launch of airmail across the nation. In the rush to prepare them in time for the first flight, plate printers inadvertently produced a series of error sheets on which the plane, engraved by Marcus Baldwin, was printed upside down.

While most of the inverts were destroyed, a sheet of 100 stamps made its way to a Washington D.C. post office where it was acquired by seasoned stamp collector William T. Robey. The philatelist, who went to purchase the stamps hoping to find inverts, would later say his “heart stood still” as he paid $24 for the rare batch, which he flipped to dealer Eugene Klein for $15,000. The Inverted Jenny has since become one of the most sought-after prizes among stamp enthusiasts, the subject of million-dollar sales and even the target of a 1955 heist.

Labeled No. 49, the Inverted Jenny recently sold by Siegel Auction Galleries, a Manhattan-based auctioneer specializing in stamps, is the finest example of the prized misprint. It was deemed “Mint Never-Hinged” by several experts, meaning it is in the same condition as when it was first sold to Robey and was never mounted.

“We have tracked each of the stamps and are certain no other example compares to this one,” said Scott Trepel, president of Siegel, in a statement. “I believe that when this stamp comes to market again it will sell for even more than it did today,” added Trepel, who has handled and sold sixty-six Inverted Jennies in his career. The buyer of the $2 million stamp wishes to remain anonymous, according to the auction house.

Who are the high-profile collectors of the Inverted Jenny?

Men stand behind sign advertising four missing stamps
A press conference for the 2016 return of an Inverted Jenny stolen in 1955. Spencer Platt/Getty Images

Over the decades, Inverted Jenny stamps have passed through the hands of several wealthy and powerful enthusiasts. Klein sold the sheet for $20,000 to businessman Colonel Edward “Ned” Green, son of the powerful financier Hetty Green (aka the “Witch of Wall Street”). Numbered and divided by Green, the stamps have since been collected by high-profile philatelists, including billionaire investor Bill Gross, Indeck Companies CEO Gerald Forsythe and late congressman Fred Frelinghuysen.

Even shoe designer Stuart Weitzman got in on the action. In 2021, a Sotheby’s auction offering up Weitzman’s collectibles included a block of four Inverted Jenny stamps that sold for $4.9 million to David Rubenstein, co-founder of the Carlyle Group (CG).

And a misprinted Jenny owned by the late investor Robert Zoellner very nearly became history when it fell out of the stamp enthusiast’s album and was sucked up by a vacuum cleaner. Fortunately, Zoellner was able to recover and repair the stamp, which was later sold by Siegel Auctions.

The enthusiasm for the misprinted stamps is so great that every movement, sale or gift, of an Inverted Jenny is logged on a website dedicated to the rare stamps, which hosts a members-only society for owners. But the location of one stamp, No. 66, remains a mystery to this day. Previously owned by collector Ethel McCoy, an arts patron and the daughter of Dow Jones co-founder Charles Bergstresser, the stamp was exhibited as part of a block of four at an exhibition in Virginia in 1955. The four Jennies were stolen, and though the three others surfaced in 1977, 1981 and 2016, McCoy’s Inverted Jenny has not yet been found.

A Rare “Inverted Jenny” Fetches a Record-Breaking $2M at Auction