Inverted JennyNowadays, stamps are just, well, stamps. You buy them in bulk, stick them on the top of envelopes and forget about them. But there are stamps so rare, so sought after that only dozens—or fewer—exist, and those few command incredible price tags.

One of those stamps, the Inverted Jenny No. 58 of 100 and the finest example of the elusive stamp known to exist, recently made headlines for its assumed $1.6 million value.

But this famous headline-making stamp leaves philatelic laymen, aka the non-stamp savvy, asking questions, like: What are Inverted Jennies, why are they “inverted,” why are they numbered to 100 and why do they command such value?

To answer those questions, we’ll revisit the history of the Inverted Jenny and how a printing error flipped the philatelic community upside down.

Some stamps are worth saving, and here’s why.

A Printing Error and a Hunch

It all started back in 1918, when a production mistake snuck past inspectors of a Washington-based printing plant. A sheet of 100 stamps depicting Jenny bi-planes were inadvertently printed upside down, hence the term “Inverted Jenny.”

Inspectors failed to spot the error, and on the sheet went into regular distribution.

The Jenny stamps were already highly anticipated, as they were the first airmail stamps ever printed. So, because of the unprecedented nature of the airmail stamp, and because the stamps were printed with two colors (in those days, printing with two colors involved a simple, error-prone technique that often resulted in inverted images), many collectors expected this inverted printing error and rushed to their local post offices in search of stamp sheets that depicted the Jenny upside down.

William Robey, an avid stamp collector, was one of those curious collectors who searched for the error stamps. But, unlike everyone else, ever, Robey found what he was looking for, a sheet of 100 Jenny stamps printed upside down.

Robey purchased the sheet of 100 Jennies for $24, the original 24-cent-per-stamp price, and quickly sold them for $15,000 to a Philadelphia stamp dealer, who, in turn, sold it for $20,000 to Col. Edward H. Green.

As the new owner of $20,000 worth of stamps, Green wanted to turn an even greater profit, and broke the sheet of 100 stamps up. Fortunately for generations of stamp collectors, he had chronological numbers assigned to each of the 100 stamps.

Green’s foresight allowed for the tracking of each of the 100 stamps. (The whereabouts of all but two of the 100 stamps are known.)

The rest is history, a history full of accidental mailings, mysterious disappearances, rogue vacuum cleaners and thousands upon thousands of dollars realized at auction.

The Million-Dollar Question

Why do Inverted Jennies command such an incredible value? Maybe it’s the fact only 100 were ever known to exist, and since their discovery and initial $15,000 sale, the price has incrementally increased throughout the decades. Maybe it’s due to their tumultuous history. As mentioned above, a stamp was accidentally mailed, one stamp was inadvertently sucked up by a vacuum cleaner and recovered, and a block of four stamps was stolen from a display case in 1955. (Those stamps have all since resurfaced.)

There are multiple possibilities for the immense value of Inverted Jennies, but there is only one certainty: the inverted Jenny is one of, if not the most, famous stamp in the world.