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Ever since the "Inverted Jenny" stamp was erroneously printed in 1918, it’s been a vehicle for collector profits.
When the United States Post Office inaugurated regular mail service by air that year, the occasion called for commemoration. And how else would the USPO commemorate something but by stamp? The patriotic red and blue issue, produced specifically for the egregiously expensive $0.24 air service, depicted a Curtiss Jenny JN-4HM, the plane tapped to become the mail truck of the skies.
The USPO rushed production of the stamp, though. The two-color composition meant the sheets had to be placed on the printing press twice, doubling the potential for error, which was already heightened by a truncated timeline. In this case, the error was an upside-down airplane, and employees discovered at least three botched sheets during production.
In collecting circles, errors often create rarity, rarity breeds desirability, and desirability commands high prices. Somehow, collectors became aware of the error before post offices received sheets for distribution. One such collector, William T. Robey, managed to secure the only known error sheet at his local office, and the market for the Inverted Jenny was born.
The sheet cost Robey $24, which, even by today's standards, seems like a flagrant sum, a postal king's ransom. He near immediately wrote a $15,000 call option on the sheet to Eugene Klein, a Philadelphia stamp dealer, which Klein swiftly exercised. You thought derivatives on collectibles were a thing of the future? Turns out they’re a thing of the past.
One day later, Klein agreed to sell the stamp to Colonel Edward H.R. Green for $20,000. A $24 sheet had increased in value by 833 times in seven days. If Alts & Ends had existed in 1918, it would've been a first-ballot "Flip of the Week" Hall of Famer. But on a price chart that would become a sky-scraping postal peak, the Jenny was still only at base camp.
Green authorized Klein to divide the sheet into single stamps and blocks of multiples for further sales activity. Before dividing it, Klein penciled a number on the back of each stamp representing its position on the sheet. And then many of them went their separate ways, finding new homes in the philatelic community.
Some met perilous fates and were lost, destroyed, or stolen. Others were damaged, with one example sucked through a vacuum cleaner. One was even used as postage and mailed, a blunder on par with Smalls slamming a Babe Ruth-signed baseball over the fence in The Sandlot. But the consistency in theme for those that survived was the progression to higher values as they surfaced on the auction block.
Take Green's plate number block of eight stamps as an example. When he passed, they sold in 1944 for $27,000. That buyer removed four stamps, and in 1954, the remaining four-stamp block sold for just $18,000. Fast forward to 1971, and the same block was worth $150,000. In the ultimate collector's wheel-and-deal, PIMCO legend Bill Gross bought it for $2,790,000 in 2005 and used it to secure a trade for the USA 1c Z Grill, which completed his collection of U.S. 19th-century stamps. Not even Sam Presti could accumulate enough first-round draft picks to strike such a decisive personal victory.
Or consider the well-documented journey of position 58. In 1998, that stamp sold at Siegel Auctions for $192,500. It sold there again in 2005, this time for $577,500, which was a record for a single. By that point, the barely hinged stamp had gained the Professional Stamp Experts (P.S.E.) distinction of an XF-Superb 95 grade. In 2016, it sold at Siegel once again, soaring to a $1,351,250 result. From 1998 to 2016, it had appreciated 11% annually.
The public eye didn't gaze upon one stamp - position 49 - for over 100 years. Klein sold it to a collector in 1918 who kept it in the family and in a safety deposit box for a century. Because of that preservation and its never-hinged status, it's considered the finest example extant, earning an XF-90 grade from the Philatelic Foundation. It sold in 2018 for $1,593,000 with premium
.As a sidenote, collectors in any category not named philately might want to brainstorm a more esteemed moniker for their hobby. “Philately” gently wafts a scent of rich mahogany, leather-bound books, and distinction that attracts wealth in ways that make other less-refined categories seem like they pierce the nostrils with B.O. by comparison.
Smells aside, that same philatelic treasure - position 49 - returned to the block at Siegel last week, selling for $2,006,000 with fees and becoming the first multi-million dollar U.S. stamp. To think it all started with one eager collector staking out the post office with $24 in hand…
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