“Let’s move a whole population… what could go wrong?”

Andrew Jackson, America’s favorite populist tough guy, decided that the best way to show Native Americans some frontier hospitality was to shove them out of their ancestral lands at gunpoint. The result? One of the most shameful and avoidable humanitarian disasters in U.S. history — the Trail of Tears.

In 1830, Jackson signed the Indian Removal Act, which might sound like a quirky real estate law if it weren’t for the fact that it led to the forced relocation of tens of thousands of Indigenous people from the southeastern U.S. to what’s now Oklahoma. Spoiler: many didn’t make it. The trip was long, brutal, and utterly unnecessary (Remini, 1981).

But Jackson was a man of conviction — unfortunately, that conviction included the belief that Native American land belonged to white farmers. When the Supreme Court actually ruled in favor of the Cherokee Nation’s sovereignty in Worcester v. Georgia, Jackson reportedly said, “John Marshall has made his decision; now let him enforce it.” Translation: I do what I want.

And do it he did. With military backing and political bluster, Jackson paved the way for a forced march of death, disease, and despair. Somewhere between 4,000 and 6,000 Cherokee died along the Trail of Tears, a grim footnote to Jackson’s “tough love” presidency.

To this day, Jackson’s face graces the $20 bill — a dark little reminder that American currency has never been allergic to irony.

Yes, Jackson restructured the presidency. Yes, he beat up a would-be assassin with his cane. But those colorful flourishes can’t — and shouldn’t — wash away the reality that he knowingly and proudly engineered ethnic cleansing, and wore it as a badge of honor.

When it comes to sheer moral failure and callous disregard for human life, this one isn’t just a blunder. It’s a national sin.

And, yes, this is a second mention.

Why revisit this? Because some failures are so vast, so morally bankrupt, and so permanently scarring that they deserve more than a single line in the hall of shame. The Indian Removal Act (May 3) was the paper; the Trail of Tears (May 6) was the blood. Jackson didn’t just sign a bill — he followed through with brutal efficiency, turning policy into atrocity. We’re mentioning it twice not by accident, but by necessity. Some presidential failures echo so loudly they can’t — and shouldn’t — be ignored after one entry.