🗓️ Mid-Month Reminder Preface:

By now you’ve probably noticed we’re not exactly handing out gold stars to the men who’ve held the highest office in the land. If you thought we were doing this just to beat up on Harry Truman, calm down — we’re equal opportunity critics. And while it’s true the editorial team wouldn’t invite Truman to poker night, this whole series isn’t about slandering reputations for sport.

It’s about perspective.

You see, Donald J. Trump, the orange hurricane of chaos, didn’t invent presidential failure. He just modernized it with social media, high-definition delusion, and a flair for self-promotion that makes P.T. Barnum look modest. But even Trump, for all his blunders, isn’t the first president to bungle the job with reckless confidence and historical consequences.

America has survived slaveholders, warmongers, incompetents, paranoids, puppets, and even a guy who couldn’t pronounce “nuclear” correctly but had the launch codes. If nothing else, this series proves that the United States — for better or worse — is remarkably resilient when it comes to surviving the men we elect to lead it.

So, as we cross the halfway mark, let’s keep looking back at the monumental messes these presidents left behind. Not to gloat, not to groan, but to remind ourselves that we’ve been here before… and, God help us, we’ll probably be here again.

📰 May 15 – James Madison and the War of 1812

James Madison, Father of the Constitution, brilliant political theorist… and the guy who got us into the dumbest war this side of Vietnam.

The War of 1812 was like Madison woke up one morning and thought, “Let’s fight the biggest empire on Earth again, but this time without an army, navy, or plan.” And just to keep things spicy, let’s pick a fight over vague maritime rights and wounded national pride.

It was supposed to be a quick “defend our honor” type of war. Instead, it turned into an aimless slugfest that got the White House torched, D.C. invaded, and half the country wondering what the hell they were fighting for. Even Congress was confused.

Madison’s logic? The British were impressing sailors — basically kidnapping Americans at sea. Which, sure, was bad. But maybe — just maybe — you don’t fight a superpower with a navy the size of a small planet unless you’ve actually built your own fleet first. Instead, we relied on militias who’d rather stay home and defend their farms from squirrels.

And let’s not forget: the invasion of Canada. Madison’s administration thought Canadians would rise up and greet American soldiers as liberators. Sound familiar? They didn’t. We got beaten back, humiliated, and stuck in a long, pointless war that ended in a stalemate. No land gained. No real victory. Just a treaty that reset things to how they were before the first shot was fired. Bravo.

The only real win was a marketing campaign — the Battle of New Orleans, where Andrew Jackson mopped the floor with the British after the peace treaty had already been signed. It was the 19th-century version of a PR stunt, and it worked. People forgot Madison botched the war and started humming “The Star-Spangled Banner” like we won something.

So why include Madison on this list? Because even geniuses can screw up monumentally. He knew how to build a republic. He just didn’t know how to defend it.