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What To Make Of The Dual Legacies Of The Dueling Andrew Jackson

He remains a complex figure in American history — a war hero, a president, a man of the people to some, and a villain to others.

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Andrew Jackson’s place on the $20 bill has about six years remaining until his image is scheduled to be replaced by Harriet Tubman, the pistol-packing Underground Railroad operator. Tubman’s bravery continued with her direct participation in the Civil War.

But before Jackson fades into obscurity, it would be fitting to recognize a remarkable man.

Foremost, Jackson was a populist. He took on the Washington insiders. Known as the “People’s President,” he ended the Federal Reserve of the day (the Second Bank of the United States) and ignored the Supreme Court. President Donald Trump even hung a portrait of Jackson in the Oval Office as one of his first acts, calling Jackson “an amazing figure in American history — very unique so many ways.”

January marks the 209th anniversary of Andrew Jackson’s improbable and crushing defeat of the British in the Battle of New Orleans. Fighting outnumbered against a better-equipped and trained force, Jackson won his victory 15 days after the War of 1812 ended with the Treaty of Ghent.

In the grand annals of American presidential history, few figures are as simultaneously awe-inspiring and confounding as Jackson. With a life story that reads more like a legend than a biography, Jackson was a man who, among other things, dueled an astonishing 103 times without earning himself a permanent residence six feet under (unlike that poor soul Alexander Hamilton who only made it to a $10 bill). Old Hickory didn’t just flirt with danger — he took it out for a candlelight dinner and then challenged it to a duel.

But let’s delve deeper into the colorful tapestry that is Old Hickory’s legacy. Picture him on the dueling field, possibly checking off another duel from his lengthy list. One wonders if he had some sort of loyalty program going on — “Survive 10 duels, get a free bullet removal!” The fact that he survived all these encounters suggests either an incredible skill or an absurd amount of luck. Either way, it earned him a spot on the $20 bill, doubling Hamilton’s currency value — perhaps a sly nod from history to Jackson’s superior dueling stamina.

Through all of this, it’s fascinating to imagine how Jackson would fare today. Would he be a viral internet sensation, known for his outrageous dueling challenges posted on social media? “Swipe right for my next duel.” Or perhaps he’d be a star on reality TV, a judge on “America’s Next Top Duelist.” And imagine him handling Twitter trolls — with his track record, they’d probably think twice before hitting “send.”

Jackson’s flair for the dramatic wasn’t confined to the dueling field. He famously teamed up with an actual pirate, Jean Lafitte, to outmaneuver the British in the Battle of New Orleans. It’s the kind of story that makes one consider the missed opportunity of a “Pirates of the Caribbean: President’s Treasure.”

However, Jackson’s life wasn’t all about swordplay and swashbuckling. His presidency was marked by actions and statements that were, to put it mildly, controversial. Take, for instance, his famous defiance of the U.S. Supreme Court. When the court ruled against his policies regarding Native American removal, Jackson allegedly responded with, “John Marshall has made his decision, now let him enforce it.” It’s the kind of brazen attitude that today might result in a flurry of opinion pieces and a trending hashtag.

Today’s Interpretation of Jackson

This brings us to the modern interpretation of Jackson. In recent years, the Democratic Party, the very institution that once celebrated him as a founding figure, has largely moved away from honoring him in their traditional “Jefferson-Jackson” dinners. Colorado’s Democratic Party renamed its event after Barack Obama, which seems a rather sedate downgrade. It seems that even his own party, which Jackson helped shape and define, has decided to give Old Hickory the cold shoulder. It’s a bit like being unfriended on Facebook by your own fan club.

And who could forget the assassination attempt on Jackson? When both pistols of his assailant misfired, Jackson, in a display of elderly badassery, proceeded to beat the would-be assassin with his cane. One can imagine Jackson’s foes thinking twice before messing with him. “Remember what happened to that guy who tried to shoot him? Yeah, he got a taste of Hickory’s walking stick. Maybe let’s not.” It’s the sort of thing you’d expect in a Quentin Tarantino film, not from a U.S. president.

In a modern context, Jackson is a figure who would be canceled today. His actions and attitudes, particularly those regarding Native American policies, would lead to a storm of Twitter threads and probably a few documentaries questioning his legacy. Yet he remains a complex figure in American history — a war hero, a president, a man of the people to some, and a villain to others.

But Jackson’s life was nothing short of a rollercoaster written by a particularly imaginative historian. He was more than just a president; he was a duelist, a pirate ally, a Supreme Court antagonist, and a man who wouldn’t let a couple of misfired pistols ruin his day. His story is a reminder that history is painted in shades of gray — and brilliant colors — rather than black and white, and the heroes of yesterday become problematic when considered with modern sensibilities.

So the next time you see a $20 bill, remember Old Hickory — a man who lived life like a character out of a tall tale, proving that sometimes truth really is stranger (and more amusing) than fiction.


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