What is it about stamps that captivates so many? These small pieces of paper, often adorned with iconic figures and historical moments, hold a unique allure. They are miniature works of art, fragments of history, and intriguing collectibles, sometimes even acting as a form of currency. For philatelists, those deeply passionate about stamp collecting, the upcoming auction of William H. Gross’s U.S. stamp collection is a monumental event. Cheryl Ganz, curator emerita of the Smithsonian National Postal Museum, describes Gross’s collection as unparalleled in private American stamp collecting history. As the world of philately anticipates this significant reveal, we delve into the captivating realm of Stamps Worth Money, exploring 10 of the most exceptionally rare and valuable stamps in American history.
1. The Enigmatic Inverted Jenny
The Inverted Jenny, a legendary printing error considered one of the most valuable stamps due to its rarity and unique upside-down airplane image.
The Inverted Jenny stands as arguably the most celebrated stamp error in U.S. postal history, shrouded in myth and highly sought after by collectors. The stamp features the Curtiss JN-4HM biplane, a significant aircraft as 95% of U.S. pilots trained on JN-4s during World War I. Adding to its appeal for philatelists, this plane was the pioneering aircraft used for delivering mail.
The source of the Inverted Jenny’s fame and value is a dramatic printing mishap. During production, the blue vignette depicting the airplane and surrounding sky was accidentally printed upside down within the correctly printed red border. This error was confined to a single sheet of 100 stamps, which was subsequently divided, resulting in mostly individual stamps circulating today, although two blocks of four remain intact. The desirability of these stamps is undeniable; in 2016, a solitary Inverted Jenny fetched a staggering $1,351,250 at auction, highlighting just how much stamps can be worth money.
The Curtiss Jenny biplanes, initially designed for military use, were adapted for airmail service with modifications including larger fuel tanks, a different engine, and a mail hopper. Interestingly, these early airmail flights were not without peril. The inaugural U.S. Post Office Department airmail flight on May 15, 1918, ended abruptly when the pilot lost his way and crash-landed in a farmer’s field, ironically adjacent to property owned by Otto Praeger, the very postmaster official overseeing airmail. Scott Trepel, president of Siegel Auction House, notes the humorous irony: “None of the first day’s mail made it. They had to send it the next day.” This mishap only adds to the lore surrounding the era of early airmail and the iconic Inverted Jenny stamp.
2. The Historic 1847 Issue Block of Ben Franklin
A block of 1847 Ben Franklin stamps, representing the first postage stamps issued by the U.S. government, highly valuable for their historical significance and pristine condition.
The year 1847 marks a pivotal moment in postal history as it was the first year the U.S. government issued postage stamps for public purchase. This legislation, passed in 1845, revolutionized mail delivery, allowing senders to prepay for postage by affixing stamps. These 1847 stamps are not just stamps; they are tangible artifacts representing the dawn of the U.S. federal postage system. Prior to 1847, while the United States Post Office Department had been established since 1792, mail delivery was primarily paid for by the recipient upon delivery.
The inaugural stamps featured two iconic figures: Benjamin Franklin and George Washington. Benjamin Franklin’s connection to the postal service is particularly rich and intriguing. In 1775, after returning from England, Franklin was appointed postmaster general of the independent colonies by the Continental Congress. However, his postal career began much earlier when the British Crown appointed him postmaster general of the American colonies in 1753, a position he shared with William Hunter. Franklin’s tenure wasn’t without controversy. He was dismissed from his Crown post in 1774 after being caught opening mail between English authorities and sharing the contents with his rebel allies – an incident known as the Hutchinson Affair. This fascinating backstory further elevates the historical and collectible value of these early Ben Franklin stamps, demonstrating how stamps worth money often carry significant historical narratives.
3. The Taxing Almanac Stamp of 1765 or 1766
An example of a Stamp Act stamp, representing a tax levied by the British Parliament on the American colonies and a significant artifact of pre-Revolutionary War tensions.
The Stamp Act, enacted by the British Parliament in 1765, is widely recognized as a key catalyst leading to the American Revolution. This act imposed a tax on various types of American paper used for legal, official, and everyday documents, including ship’s papers, business licenses, calendars, declarations, inventories, and even playing cards. The “stamp” itself was applied to the paper to signify that the required tax had been paid. While the financial burden of the Stamp Act was relatively small, and it was repealed the following year, its impact was profound and far-reaching.
The American colonies vehemently opposed the Stamp Act, viewing it as taxation without representation – a fundamental challenge to their rights and autonomy. The act ignited widespread colonial outrage, leading to mob violence and intimidation tactics that forced stamp tax collectors to resign and prevented ships carrying stamped papers from docking in seaports. Colonial figures like Patrick Henry and newspapers effectively used the Stamp Act as a rallying cry, highlighting perceived English tyranny and fueling the growing movement towards revolution. This stamp, though not a postage stamp in the modern sense, is a powerful historical artifact that speaks volumes about the pre-Revolutionary era and the burgeoning sentiment against British rule, making it a valuable piece of history for collectors interested in stamps worth money with significant historical context.
4. The Rare ‘Blue Boy’ Alexandria Postmaster’s Provisional
The ‘Blue Boy’ stamp, a unique and exceptionally rare provisional stamp from Alexandria, Virginia, known for its distinctive blue color and historical significance.
In the realm of U.S. stamp collecting, the “Blue Boy” holds an almost mythical status, often compared to the iconic Mona Lisa in terms of its rarity and allure. Between 1845, when Congress established standardized postage rates, and 1847, when the first federal postage stamps were introduced, postmasters in various counties and cities across the 29 states issued their own provisional stamps. These postmasters displayed considerable creativity in their designs. For instance, the St. Louis provisional stamps famously feature two bears flanking the United States coat of arms.
Provisional stamps from Alexandria, Virginia, are particularly noteworthy, especially considering Alexandria’s unique historical context of being retroceded to Virginia from the District of Columbia during this period. Only seven Alexandria provisional stamps are known to exist today, with the majority being “buff” or brownish-yellow in color. The “Blue Boy” stands alone as the only known example in a vibrant blue hue. This exceptional stamp was discovered on a love letter sent in 1847, a letter that was originally intended to be burned by the recipient. Its distinctive color and romantic origin story earned it the moniker “Blue Boy,” drawing a parallel to the famous portrait of a boy in blue attire by English painter Thomas Gainsborough. The “Blue Boy” exemplifies how stamps worth money can possess not only monetary value but also captivating stories and unique historical connections.
5. The Inverted Center Errors of the 1869 Pictorials
An inverted 1869 pictorial stamp featuring an upside-down image of the Signing of the Declaration of Independence, a sought-after error from the first U.S. bicolor stamps.
Stamp collectors are drawn to rarities, historical firsts, and errors – and the 1869 Pictorial stamps embody all three, intertwined with a dash of political intrigue. While issued during President Ulysses S. Grant’s administration, the concept for these stamps originated in 1868, a politically charged period following Andrew Johnson’s impeachment. These stamps, highly controversial and discontinued after just one year of production, marked several firsts for U.S. postage. They were the first to be printed in two colors and the first to depict scenes rather than solely portraits, such as Columbus’s arrival in America.
The 1869 Pictorials also represent the first instance of a printing error by the Post Office Department. The two-color printing process required each color to be applied separately. Careless handling led to several sheets being placed upside down in the press, resulting in the first American invert errors. Among these errors, a four-stamp block of the 24-cent inverts, featuring John Trumbull’s painting Declaration of Independence, gained international notoriety when it was auctioned in London in 1938. This auction was groundbreaking as it marked the first time a transatlantic telephone line was used to purchase a lot at an auction, underscoring the global appeal and significant value associated with these stamps worth money.
6. The Precious Two-Cent Blue Hawaiian Missionary
A Blue Hawaiian Missionary stamp, considered exceptionally valuable due to its rarity and historical context as one of the earliest stamps issued in Hawaii.
In 1963, Life magazine famously declared this stamp to be “Pound for pound, the most valuable substance on earth,” a testament to its incredible rarity and desirability among collectors. The Blue Hawaiian Missionary stamp dates back to 1851 when Hawaii was an independent kingdom and a popular destination for American missionaries spreading Christianity. Despite Hawaii’s sovereignty, its postal system was surprisingly well-connected to the U.S., with an American postmaster in Honolulu and strong ties to the San Francisco post office. Collectors treasure these stamps not only for their scarcity but also for their distinctive, almost whimsical numerals.
Interestingly, the 2-cent denomination had limited practical use. Its primary purpose was for postage on newspapers or for the captain’s fee – ship captains received 2 cents for each letter they carried. Fans of Audrey Hepburn might recognize a stamp resembling this one from the 1963 film Charade, where a Hawaiian Missionary stamp plays a crucial role in the plot. However, the film contains a slight inaccuracy: the stamp in Charade is depicted as a 3-cent stamp, while no 3-cent Missionary stamp actually existed. The Missionary series only included 2-cent, 5-cent, and 13-cent denominations, a minor detail that doesn’t diminish the real-world value and historical fascination surrounding these stamps worth money.
7. The Tale of the 1860 Stolen Pony Cover
The 1860 Stolen Pony Cover, a rare postal artifact that tells a story of the Pony Express and the dangers faced by riders in the American West.
This unique postal cover provides a glimpse into the romanticized yet often perilous world of the American West and the legendary Pony Express. Established in 1860, the Pony Express was a private mail service that employed a network of young riders and relay stations to deliver mail across the country in approximately 10 days – a significant speed advantage over stagecoach or ship. The cover is stamped with the name of its parent company, Central Overland California and Pike’s Peak Express Company. The story behind this particular cover is both dramatic and historically significant. In 1860, a Pony Express rider traveling eastward through Nevada vanished. His mailbag was recovered two years later, and two covers from that bag survived, bearing the handwritten inscription: “Recovered from a mail stolen by the Indians in 1860.”
Despite the enduring legends surrounding the Pony Express, including claims of riders like Buffalo Bill Cody and Wild Bill Hickok (neither of which are substantiated), the service itself was short-lived, lasting only 19 months. It was, in essence, a publicity venture by three businessmen seeking to secure a lucrative government mail contract. The “Stolen Pony Cover” is a tangible piece of this brief but captivating chapter in American history, making it a valuable collectible for those interested in stamps worth money with a Wild West narrative.
8. The Pan-American Inverts and Presidential Tragedy
A Pan-American invert stamp, a sought-after error from the commemorative series for the Pan-American Exposition, linked to the historical event of President McKinley’s assassination.
Transportation served as the central theme for the six commemorative stamps issued in 1901 to celebrate the Pan-American Exposition held in Buffalo, New York. The series featured images of engineering marvels like the bridge at Niagara Falls and the steam engine. Due to their bicolor printing process, these stamps were susceptible to errors, and inverts occurred on the 1-cent, 2-cent, and 4-cent denominations.
The Pan-American Exposition is now perhaps less remembered for its stamps or even for Jumbo, a massive 9-ton elephant with a dramatic history, and more for the tragic assassination of President William McKinley on September 6th. President McKinley was fatally shot by anarchist Leon Czolgosz while greeting the public at the exposition. He succumbed to his injuries eight days later. Vice President Teddy Roosevelt, initially confident in the president’s recovery, had even gone on a camping trip in the Adirondacks. The Pan-American Inverts, therefore, are not just philatelic errors but also poignant reminders of a significant and somber moment in American history, adding another layer of value to these stamps worth money.
9. The Intriguing CIA Invert
The CIA invert stamp, a relatively modern error stamp with a fascinating story involving CIA agents and a subsequent scandal, adding to its collector’s value.
The world of espionage and stamp collecting surprisingly intersect with the story of the CIA Invert. Between 1975 and 1981, the Post Office released a series of Americana stamps, four of which depicted light sources. Among these, a $1 stamp featuring a colonial rush lamp and candle holder was printed as an invert on a single sheet of 100 stamps. In a plot twist worthy of a spy novel, nine CIA agents stationed in McLean, Virginia, discovered the error in 1986 and purchased the pane containing the 95 remaining stamps (five had unknowingly been sold and used as regular postage).
The agents discreetly replaced the rare stamps with regular $1 stamps and later sold a pane of 85 inverted rush lamp stamps (along with one damaged stamp) to a collector for $25,000. Each agent kept one stamp for themselves as a memento. However, their clandestine acquisition soon led to a scandal. The agency demanded the agents return the stamps, arguing they were purchased with taxpayer funds, or face termination. Four agents returned their stamps, four resigned or were fired, and one agent claimed to have lost their stamp, managing to keep their job. This cloak-and-dagger tale adds a unique layer of intrigue and modern history to the CIA Invert, making it a particularly captivating and valuable stamp for collectors interested in stamps worth money with a story.
10. The Final Invert: Stock Exchange Invert
The Stock Exchange invert stamp, the most recent invert error from the US Post Office, commemorating the New York Stock Exchange and valued for its modern rarity.
The Stock Exchange Invert holds a unique distinction as the last invert error produced by the United States Post Office, occurring in 1992. This error appeared on a stamp commemorating the 200th anniversary of the New York Stock Exchange (NYSE). Only 56 of these invert stamps are known to exist, making them exceptionally rare in the modern era of stamp production. The stamp features a green border with red numerals and includes two inverted images: a scene of contemporary traders in the bustling stock exchange and an exterior view of the NYSE’s neoclassical building at 11 Wall Street.
The New York Stock Exchange’s origins trace back to May 17, 1792, when 24 stockbrokers signed the Buttonwood Agreement. This agreement stipulated that these brokers would exclusively trade with each other and set a commission rate of 0.25 percent. The signing took place outdoors at 68 Wall Street, under a buttonwood tree. The agreement was forged in response to a financial panic triggered by William Duer’s excessive borrowing and subsequent defaults earlier that year. The Stock Exchange Invert, as the most recent US invert error and a commemoration of a vital financial institution, holds a special place in philatelic history, representing a valuable and relatively modern example of stamps worth money.
Exploring these ten exceptional stamps reveals not only their monetary worth but also the rich tapestry of history, human error, and captivating stories that they encapsulate. For collectors and enthusiasts alike, stamps worth money are more than just adhesive postage; they are miniature portals to the past, each with a unique narrative waiting to be discovered.
