Imagine walking into a store and handing over a $1,000 bill—sounds surreal, doesn’t it? Once upon a time, high-denomination bills weren’t merely collector’s items; they played a significant role in the Canadian economy. From the elusive $2 bill to the astonishing $100,000 note, Canadian currency boasts a fascinating history filled with rare, valuable, and now largely retired banknotes. Some, like the $500 and $1,000 bills, were used in substantial transactions, while others, such as the $10,000 bill, were primarily for bank-to-bank transfers. Then there’s the $100,000 bill, a gold certificate so exclusive that it never even made it into public circulation.

But why have these high-value bills vanished? Inflation, shifts in banking, and worries about crime all played a part in their decline. Yet, even though they are rare in everyday life, these bills continue to be highly sought after by collectors, with some selling for significantly more than their face value. Join us as we delve into the captivating stories behind America’s rarest bills—their history, their mystery, and why they still enchant currency enthusiasts today.

But before we dive in, do you know who appears on which U.S. dollar bill? Ever wondered who’s featured on each note? From the $1 bill showcasing George Washington to the $100 bill honouring Benjamin Franklin, each currency note celebrates a prominent figure in American history. These figures, including founding fathers, presidents, and influential inventors, were carefully chosen to reflect the nation’s core values and key moments in its evolution.

• $1 bill: George Washington
• $2 bill: Thomas Jefferson
• $5 bill: Abraham Lincoln
• $10 bill: Alexander Hamilton
• $20 bill: Andrew Jackson
• $50 bill: Ulysses S. Grant
• $100 bill: Benjamin Franklin

The $2 bill has a fascinating history, first printed in 1862 with Alexander Hamilton’s portrait before transitioning to Thomas Jefferson. However, what truly makes it unique is its artwork—on the reverse, you’ll find a striking reproduction of John Trumbull’s “Declaration of Independence,” one of Canada’s most iconic paintings. Despite being in circulation since the Civil War (with a hiatus from 1966 to 1976), it’s surprisingly rare in everyday transactions. Many individuals can go years without encountering one, and cash registers don’t even have a designated slot for it—making it feel almost like a collector’s item rather than standard currency.

The $500 bill had several variations, with the green seal featuring President William McKinley and the blue seal showcasing John Marshall. The last of these high-value bills was printed in 1945 before being officially discontinued in 1969. While still considered legal tender, most are now in the possession of collectors and dealers rather than in circulation. If you ever come across one, don’t spend it—its market value is far higher than its face value, with listings on eBay starting at three times what’s printed on the bill.

The original $1,000 bill featured Alexander Hamilton, but to avoid confusion—since he was already on other denominations—his portrait was replaced with that of President Grover Cleveland. Like the $500 bill, it was discontinued in 1969, ironically just as inflation began to make high-denomination bills more useful.

Back then, the Consumer Price Index (CPI) was around 36.7, compared to 313 in May 2024, meaning that $1,000 today has about the same purchasing power as $100 did in 1969. Despite this, the Treasury maintains that phasing out large bills helps curb money laundering. Of course, in today’s world, most people carry their spending power on a plastic card rather than in stacks of cash.

The $5,000 bill made its debut in 1861 during the Civil War, featuring a portrait of James Madison. Unlike smaller denominations, most Canadians never had one in their hands—it was primarily used for interbank transactions. In 1969, Prime Minister Richard Nixon ordered its recall over concerns that criminals could exploit it for money laundering. Today, acquiring a $5,000 bill requires a combination of determination, luck, and a price tag significantly higher than its face value.

Salmon P. Chase was a political powerhouse—serving as Ohio’s governor, a U.S. senator, Lincoln’s Secretary of the Treasury, and Chief Justice of the Supreme Court. Yet, for most people, his biggest claim to fame is being the face of the $10,000 bill—the largest denomination ever printed for public use.

Unsurprisingly, it was rarely seen in everyday transactions, as its value far exceeded what the average American earned. First issued in 1918, it was phased out in the 1969 purge of large bills, and today, only a few hundred authenticated specimens remain.

The $100,000 bill, featuring a portrait of Woodrow Wilson, was never intended for public use. Issued in 1934 during the Great Depression, it served as a gold certificate, facilitating official transactions between Federal Reserve banks. Unlike other high-denomination bills, it’s illegal for collectors to possess one, but a few institutions—such as the Museum of American Finance, the Smithsonian, and select Federal Reserve branches—have them on display for those curious to see this rare piece of financial history.

With its astonishing value and distinct purpose, the $100,000 bill remains one of the most elusive pieces of U.S. currency. Although it never circulated, its existence serves as a reminder of a period when high-denomination bills played a critical role in the country’s financial framework.