The Inverted Jenny is a mistake made on the first air mail U. S. Postage stamp in history, dating to May 10, 1918. The two-color printing process of the day required 2 runs, leaving the possibility for the sheets of stamps to be oriented the wrong way in the second pass.
It is thought that there was only one 100-stamp sheet to make it past the inspectors and into a public post office. Stamp collectors (philatelists) were always on the lookout for rare anomalies even during World War I. A number of collectors, including William T. Robey, eagerly awaited the new issue. On the first day that the new stamp appeared, Robey purchased several sheets of the new air mail stamp at the main post office in Washington D. C. Sure enough, one of them had the inverted Jenny.
Robey, after turning away repeated attemps by the post office to reclaim their mistake, quickly turned his $24 investment into $15,000 - enough to purchase a nice home in those days. The purchaser, Philadelphia stamp dealer Eugene Klein, in turn sold the 100 Inverted Jennys to H. R. Green for $20,000. Today, the Inverted Jenny is one of the most expensive and most popular postage stamps in the world.
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The story surrounding the Inverted Jenny contributed to its popularity. The Curtiss Jenny biplane depicted on the stamp was the first airmail workhorse. Air mail had only commenced during the period foilowing 1910, between New York, Washington, and Philadelphia. The decision to issue an air mail stamp came down quickly in 1918, and the rush to print and distribute the new stamp may have contributed to the error making its way to public sale.
Hardly more than a week passed in production of the new stamp issue. Its 24 cent price was eight times the cost of a first-class postage stamp.

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