The Debunker: Did Teddy Roosevelt and His Rough Riders Take San Juan Hill?

by Ken Jennings

In a series of “Debunker” columns from a few years back, Ken Jennings shattered a few beloved myths about the presidency—Abraham Lincoln didn’t write the Gettysburg Address on an envelope, JFK didn’t kill the hat. So why take on four more White House whitewashes this month? It’s a matter of some urgency: Ken has a fun new book out this month about such matters. So get ready to whistle along to “Fail to the Chief” as KJ blows up everything you thought you knew about the leader of the free world.

The Debunker: Did Teddy Roosevelt and His Rough Riders Take San Juan Hill?

“It was a splendid little war,” ambassador John Hay wrote to his friend Theodore Roosevelt in 1898, reminiscing about the eight weeks of the Spanish-American War. Leaving aside the little matter of 17,000 deaths, the war with Spain was indeed splendid for the political career of Roosevelt, who had resigned his post as Assistant Secretary of the Navy in order to fight in Cuba. The legend of Roosevelt leading his “Rough Riders” up San Juan Hill and saving the day is probably the most iconic thing people remember about the war. But most people’s knowledge of Teddy’s ragtag band of volunteers is a little, well, rough.

thanks skemmis

For one thing, Teddy Roosevelt didn’t lead the 1st United States Volunteer Cavalry, better known as the “Rough Riders.” Sure, he organized the group of college athletes and cowboys, but he made sure a real military man—army colonel Leonard Wood—was in charge. Secondly, the “Rough Riders” didn’t really ride anywhere. Due to a shortage of transport, most of the “cavalry’s” horses never made it to Cuba, staying stuck in Tampa, Florida for the duration of the war. “Roosevelt’s Rough Riders” joked that they could more accurately be called “Wood’s Weary Walkers.”

During the Battle of San Juan Hill, on July 1, 1898, Roosevelt was indeed leading the company, Wood having received a field promotion to brigadier general. Teddy even had a horse! But here’s the real kicker: the famous heroic “charge” that Roosevelt traded on for the rest of his career wasn’t up San Juan Hill: it was to a nearby point called Kettle Hill, named for an old kettle that was found sitting atop it. (Two regiments of “Buffalo soldiers,” African-American infantrymen, fought just as bravely on Kettle Hill, but to much less public acclaim.) By the time Roosevelt’s men got to the top of the actual San Juan Hill, the fighting was over and the Rough Riders were sent back to hold Kettle Hill. But I get it, Teddy: you don’t want to get famous for taking a hill named for an old kettle. Pretend it was the one with the sexy Spanish name. Good choice.

Quick Quiz: “San Juan” is also the name of the capital of what island, which became a U.S. colony at the end of the Spanish-American War?

Ken Jennings is the author of six books, most recently his Junior Genius Guides, Because I Said So!, and Maphead. He's also the proud owner of an underwhelming Bag o' Crap. Follow him at or on Twitter as @KenJennings.