You pull a twenty out of your wallet to pay for a coffee. You see that familiar, wild-haired face staring back at you. It’s Andrew Jackson. But if you’ve ever stopped to look at him and wondered, Wait, why this guy?—you’re not alone.
In fact, the more you learn about the guy, the weirder it gets.
There is a massive historical irony sitting in your pocket. Andrew Jackson actually hated paper money. He didn't just dislike it; he spent a good chunk of his presidency trying to kill the very system that now prints his face on linen-and-cotton bills every single day.
Honestly, if Jackson could see a modern Federal Reserve Note with his portrait on it, he’d probably lose his mind. He’d likely consider it a personal insult.
The Mystery of 1928: How He Got There
Believe it or not, the U.S. Treasury doesn't actually have a clear, written record that says, "We picked Jackson because of X, Y, and Z."
Before 1928, Grover Cleveland was the face of the twenty. When the Treasury Department decided to standardize the size of our bills and update the look, they swapped Cleveland for Jackson.
When people asked why, the official line from the Treasury was basically: "He's famous."
In a 1929 New York Times article, officials claimed they chose certain statesmen because their faces were "most familiar" to the public. They basically did a 1920s version of a brand recognition study. Jackson was a war hero. He was the "People’s President." Even a hundred years after his time in office, he was a celebrity.
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But there’s a deeper theory. Some historians think it was a bit of a political jab.
See, 1928 was the 100th anniversary of Jackson’s first presidential election. Putting the man who tried to destroy central banking onto a central bank note is the ultimate "we won" move by the banking establishment. It's like putting a famous vegan on a steakhouse menu.
The Bank War: Why Jackson Would Hate Your Wallet
To understand why this is so funny (or tragic, depending on your view), you have to look at the Bank War of 1832.
Jackson was a "hard money" guy. He believed that the only real money was gold and silver—what they called "specie." He thought paper money was a scam used by rich bankers to cheat regular people. He famously said that the Second Bank of the United States was a "monster" that threatened the liberty of the American people.
He didn't just talk. He acted.
- He vetoed the bill to renew the National Bank's charter.
- He pulled all the government’s deposits out of the bank.
- He issued the "Specie Circular," which required people to buy government land with actual gold or silver instead of paper.
He basically set fire to the precursor of the Federal Reserve. And yet, here we are, nearly 200 years later, using his face to represent the very "imaginary" paper value he loathed.
The Darker Side of the $20 Legacy
It’s not just the banking stuff that makes people tilt their heads at Jackson’s portrait.
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Over the last few decades, the conversation has shifted toward his actual record as a leader. While he was the champion of the "common man" (specifically white men who didn't own land, who got the vote because of his movement), he was also the architect of the Indian Removal Act.
This led directly to the Trail of Tears.
For many Americans, especially within Native communities, seeing Jackson on the most circulated bill in the country isn't just an "ironic" historical quirk. It’s a reminder of state-sponsored forced migration and tragedy.
Then there’s the fact that he was a wealthy enslaver. When you add all that up, you start to see why there’s been such a massive push to change the face of the twenty.
Is Harriet Tubman Still Replacing Him?
You’ve probably heard the rumors that Jackson is on his way out.
The plan to put Harriet Tubman on the $20 bill has been a bit of a rollercoaster. It was first announced back in 2016 under the Obama administration. Then it got delayed. Then it got fast-tracked again.
As of right now, here is the deal:
The Treasury is still working on it, but you won't see Tubman in your ATM for a while. Redesigning currency is a logistical nightmare because of anti-counterfeiting tech.
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The current timeline suggests:
- The new $10 bill (featuring women from the suffrage movement) arrives around 2026.
- The $5 bill follows in 2028.
- The Harriet Tubman $20 bill is currently slated for a 2030 release.
When it finally drops, it’ll be a historic moment—the first time a Black woman has ever been the face of U.S. paper currency.
What You Can Do Now
So, what does this mean for you?
Next time you’re at a bar or a grocery store and you hand over a twenty, you’ve got a great trivia card in your hand. You’re holding a piece of paper that represents a system the guy on the front tried to destroy.
If you're interested in the future of the bill, you can actually track the progress of the "New 20" through the U.S. Currency Education Program. They post updates on security features and design reveals.
If you're a history nerd, I'd highly recommend looking into the "Specie Circular" or the "Panic of 1837." It explains a lot about why our economy looks the way it does today. Jackson might have lost his war against paper money, but his influence on how we think about "the little guy" vs. "big banks" is still very much alive.
Keep an eye on your change. By 2030, the "Jackson" might just become a collector's item while the "Tubman" takes over the streets. For now, we're stuck with the irony.
Check your wallet. See if you have any "Series 2017" or "Series 2013" bills. Those are the ones where Jackson's face is slightly off-center—a design choice made in the 90s to make room for a watermark and a security thread. Even the way he’s framed on the bill has changed, even if the man himself hasn't.