Rough Riders

Teddy Roosevelt spent time in the military as an officer. He was the leader of a group known as the Rough Riders, which were the first volunteer cavalry in the U.S. Army. Their most famous battle was at San Juan Hill, in Puerto Rico. At this battle, Teddy Roosevelt led his Rough Riders up San Juan Hill against overwhelming odds to defeat the Spanish, and take over the island. Teddy's reputation as a strong leader gains great strength as a result of this battle.

The best known representation of Teddy Roosevelt as a Rough Ride comes from the Night at the Museum movies, where he is portrayed by the late Robin Williams.