For Sale: A Stamp So Famous It Appeared on ‘The Simpsons’

Good morning. It’s Tuesday. We’ll look at one of the most famous mistakes ever made — a postage stamp with an upside-down airplane. We’ll also see what the guilty plea by Representative George Santos’s campaign treasurer might mean for Santos himself.

Credit…Chang W. Lee/The New York Times

I don’t usually throw around big numbers here, but just this once, let’s talk percentages — huge percentage gains for a tiny postage stamp.

The first time it was sold, in 1918, the stamp in question cost 24 cents. It was one stamp on a sheet of 100.

The sheet was resold for $15,000 less than a week later, so the value of each stamp would have rocketed to $1,500 — an increase of 624,900 percent. The sheet was sold again the next day for $20,000, putting a value of $2,000 on each stamp — an overnight gain of a further 33.33 percent.

The sheet of 100 was eventually broken up into several blocks of four stamps and many individual stamps. The one in question, No. 49 on the page of 100, apparently spent decades in one safe deposit box or another in the Midwest until it was sold in 2018 for $1.593 million — an increase of 663 million percent from the original 24 cents. Now a Manhattan auctioneer is preparing to sell it again, with a presale estimate of as much as $2 million.

No. 49 is an “Inverted Jenny,” one of the most famous mistakes in stamp history. It is a mistake because on the stamps in this sheet, the little blue airplane in the center, a biplane from the early days of airmail that was known as a Jenny, was printed upside down.

No other sheets of Inverted Jennies are known to exist, and stamp experts say No. 49 is in much better shape than some of the other stamps from the sheet.

This one was not sucked up by a vacuum cleaner, as one Inverted Jenny was. It was not stuffed into a locket, as another was, as a present. This one was never cut and re-perforated, as one was after it was stolen.

Robert A. Siegel Auction Galleries, which will sell No. 49 on Nov. 8, had it graded by two organizations of stamp experts. Each gave it a 95 on a scale of 100, a rating that Scott Trepel, the president of Siegel, said was the highest grade an Inverted Jenny “has ever received or will receive.” Robert Rose, the chairman of the Philatelic Foundation, one of the groups that graded it, said, “It’s really one of a kind.”

The Inverted Jenny is so well known that it figured in a scene in an episode of “The Simpsons” about a community yard sale. “Oooh, five cents each,” Homer says, reaching into a box and pulling out pieces of history like a parchment copy of the Declaration of Independence and the first comic book featuring Superman. He discards both, saying, “Junk.”

Next he pulls out a sheet of Inverted Jennies. “The airplane’s upside down,” he says, throwing the sheet away.

Trepel said the error had happened in the rush to print the stamps in time for the first airmail flight. When the press had been inked for the biplanes and the sheet was fed in, the Jennies came out wrong. Trepel said that any other sheets printed that way had been destroyed.

But the one sheet of 100 stamps went out into the world. A financial clerk named William Robey bought it at a post office during his lunch hour, paying $24, the face value of the 100 stamps.

He did not make the mistake that Homer Simpson made. He hustled out of the post office and later dodged postal inspectors who went looking for him in a frantic effort to get back that single sheet of paper. And with the $14,976 he pocketed when he sold the sheet for $15,000, Robey got himself a car. He might have done well to spend more time learning to drive it. He crashed through the garage that came with the house he also bought.

“I’ve seen everything — the good, the bad and the ugly,” said Trepel, who said he had handled 66 of the Jennies, selling some of them more than once. “This one, hidden away the way it was, the color’s fresh. The paper’s bright. It would be a beautiful stamp even if it didn’t have the invert.”


Enjoy a mostly sunny day in the mid-60s. At night, it will be partly cloudy, with temperatures in the low 50s.


In effect until Nov. 1 (All Saints Day).

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Why a fake loan could be real trouble for Santos

Credit…Kenny Holston/The New York Times

How did Representative George Santos suddenly come up with enough money to lend his campaign $500,000?

The answer, as our Grace Ashford explains, is straightforward: He did not.

That could have ramifications for Santos’s federal criminal case. He has pleaded not guilty to 13 felonies in three unrelated financial schemes.

But last week his campaign treasurer, Nancy Marks, pleaded guilty to one count of conspiracy related to her oversight of Santos’s finances. And it is clear that prosecutors see a connection between Marks’s case and Santos’s. The same team of federal prosecutors brought both cases to court; both proceedings share a court docket number; both went before the same judge, Joanna Seybert.

Santos, a Republican whose district covers parts of Queens and Nassau County, has not been charged with falsifying the loan or with other campaign finance violations, and Marks’s lawyer has said that the treasurer is not cooperating with prosecutors. But Santos’s apparent proximity to the criminal activity acknowledged by Marks would seem to leave him vulnerable to additional charges.

The loan that prosecutors say was fictitious was first listed in the Santos campaign’s quarterly report in April 2022, seven months before the election. It bolstered Santos’s image as a candidate wealthy enough to underwrite his bid for office, dissuading would-be challengers from taking him on in the primary.

Another potential benefit came when he won the seat. As a member of Congress, he would have been able to continue to accept donations once he started running for re-election. If he raised enough, he could “repay” the fictional loan, potentially pocketing $500,000 in contributions.

Santos’s loans to his campaign have long drawn scrutiny. When he ran for the House in 2020 and lost, he reported having lent himself $80,000, although his financial disclosures put his annual salary at only $55,000 and said he had no savings.

But in 2022, he claimed to have made $750,000 in salary, plus more than $1 million a year in dividends from his company, the Devolder Organization — even though the company had no visible footprint or website.

Santos has said nothing about Marks’s guilty plea. His lawyer, Joseph Murray, declined to answer reporters’ questions outside the court last week.

Santos himself, on social media, continued to sound defiant. “I dare anyone to find an elected who engages with the people more than I do,” he said on Friday.


Summer ’22

Dear Diary:

It was summer 2022. I was running with my friends at the time — 10 of them, plus my older brother — from the Museum of Modern Art to Penn Station to catch a 6:30 train back to New Jersey for an 8:30 reservation at Olive Garden.

The air smelled like falafel, and the city around us felt as alive and young as we did. I was about to turn 16. I was in New York, and the only bad thing I could imagine happening to me at that moment was missing the 6:30 train.

The people running along behind me were my best friends, girls I had whispered secrets to at sleepovers and made popcorn with in the microwaves in their kitchens.

It did not occur to me that within a year, I wouldn’t speak to any of them anymore, not a single one, or that precisely a year later, around the time of my 17th birthday party, I would uncap my pen and cross their names off the guest list.

None of that mattered — nothing mattered, except catching the 6:30 train.

I waved my hand in the air and, as the hazy New York sunset swallowed us whole, called out to my friends to follow me because our train was leaving in five minutes.

— Preeya Govil

Illustrated by Agnes Lee. Send submissions here and read more Metropolitan Diary here.

Glad we could get together here. See you tomorrow. — J.B.

P.S. Here’s today’s Mini Crossword and Spelling Bee. You can find all our puzzles here.

Melissa Guerrero and Ed Shanahan contributed to New York Today. You can reach the team at [email protected].


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