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Theodore Roosevelt resigned his post as Assistant Secretary of the Navy and helped form the 1st US Volunteer Cavalry, known commonly as the "Rough Riders," in 1898 after the outset of the Spanish-American War. After forming the regiment and training the men, he got his unit into battle at the Battle of San Juan Hill, in which the Rough Riders charged Kettle Hill on the San Juan Heights near Santiago, Cuba on July 1, 1898. TR was the Lieutenant Colonel of the outfit, second in command to Colonel Leonard Wood.

Interestingly, the 1st Volunteer Cavalry had to leave its horses in Florida to make it to the war at all; the troop transports were completely full and did not have room for the entire unit even without the horses and cavalry accoutrements.

For leading the charge on Kettle Hill, Theodore Roosevelt got plenty of good press back home, which helped him in his subsequent bid for Governor of New York, then shortly thereafter, for Vice President of the United States. Roosevelt was posthumously awarded the Congressional Medal of Honor by President Bill Clinton.

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