On May 14, 1918, Mr. William T. Robey paid $24 for a sheet of 100 commemorative stamps at his local post office in Washington, D.C. The stamps pictured the Curtiss JN-4H airplane (which was nicknamed the Jenny), which was to be used the next day in the very first airmail flight. On the sheet that Robey purchased, each of the Jennys was flying upside down.
Eight other 'inverted Jenny' stamp sheets had been produced, by accident, probably when the printer had reversed the plate that printed the planes, but all of the other sheets had been intercepted by the post office. Robey did not know this and decided that he needed to make a quick sale of his "inverts" before any of the others hit the market and devalued his prize; so six days later he sold the sheet of "inverts" to a stamp dealer for $15,000. The dealer already had an offer on the table from a collector for $20,000! Prices rose to more than $300 for each stamp, but this was only the beginning.
In 1933, a block of four "inverted Jennys" fetched $15,000 and by 1959, a single invert was worth $6,400. In 1982 the price for an invert had reached a whopping $198,000. In November 2007, a single inverted Jenny was sold at an auction for $977,500!
In an ironic aside, the very first airmail flight had ended with the real Jenny, bearing the same tail number as the one on the stamp, upside down also....in a field.
The unfortunate pilot of the first leg of the maiden airmail flight, Lt. George Boyle, was not injured when he crashed, but was a little more than embarassed. The historic take-off, which was to be witnessed by President Woodrow Wilson, almost didn't...take off. Boyle sat in the cockpit, shouting "Contact!", while mechanics tried desperately to get the engine to start. Eventually they discovered that the gas tank was empty. Once the plane was fueled, the Jenny rose to the sky, but instead of heading north, Boyle headed south. An hour later, the coordinator of the U.S.Post Office's new airmail service got a phone call from Boyle, confessing that his compass had gotten "mixed up" and that he had crashed in a Maryland cornfield. A car was sent to retrieve the downed pilot and the three sacks of mail.