CinC Theodore “Teddy” Roosevelt: The Rough Riders

Welcome to the Medal of Honor podcast, brought to you in partnership with the National Medal of Honor Museum. I’m Ken Harbaugh. In each episode, we’ll learn about a different service member who has distinguished him or herself through an act of valor.

Theodore “Teddy” Roosevelt was born on October 27th, 1858 in New York City. Roosevelt’s childhood was riddled with health issues, but his family was affluent and able to afford private tutors to educate him. He attended Harvard University and was elected to the New York State Assembly at 23 years old. He held several other public positions, and eventually was appointed assistant secretary of the Navy by President William McKinley.

In this position Roosevelt advocated for war with Spain, and when war was declared in 1898, he resigned from his post and volunteered to serve in the Rough Riders, a volunteer cavalry force in the U.S. Army. He later said about this decision “I had always felt that if there were a serious war, I wished to be in a position to explain to my children why I did take part in it, and not why I did not take part in it.”. Many believe this sentiment was influenced by his father’s decision not to serve in the Civil War, which historians suggest Roosevelt didn’t approve of.

In preparation for fighting in the hot Cuban climate, men from primarily the American southwest were recruited to the Rough Riders. By joining and becoming second in command, Roosevelt inadvertently attracted a wide range of volunteers to the Riders, from glee-club singers to Ivy League athletes. Nevertheless, Roosevelt and their commander Colonel Leonard Wood trained them so well that they were sent to fight, unlike many other volunteer companies which stayed home.

On July 1st, 1898, near Santiago de Cuba, Roosevelt and the other Rough Riders fought in the Battle of San Juan. In the early morning, the Americans split up into two flanks to attack two nearby hills. The first was tasked with capturing San Juan Hill. The Rough Riders fought in the second flank, which was led by Roosevelt with the goal of capturing Kettle Hill.

In order to protect himself from the 100 degree heat, then Lieutenant Colonel Roosevelt cleverly attached a blue polka-dot scarf, the unofficial insignia of a Rough rider, in a semicircular screen that dangled from the brim of his sombrero, protecting him from the sun. With the scarf fluttering in the wind, Roosevelt charged. He and his troops raced through a shower of bullets, but the Rough Riders, who followed Roosevelt, were stunned by the soldiers and horses that began to litter the mud in front of them. Knowing they were vulnerable, they quickly shook off their fears until they reached a patch of waist high grass near the bottom of Kettle Hill. Vulnerable on top of their horses, most of the Rough Riders had dismounted to hide in the grass- but not Roosevelt. Showing no fear, he remained on his mount and inspired his troops to attack the hill. Fighting his way through bullets and wire fences, Roosevelt miraculously reached the top of the hill unscathed, claiming Kettle Hill for the Americans. From the summit he could see that the first flank had still not captured their objective. He knew they needed his help, so with only 4 or 5 men, Roosevelt led the charge over to San Juan Hill. He and his men came under heavy fire in the open countryside, but they weren’t deterred. Roosevelt reached the enemy trenches first, quickly killing an enemy with his pistol. This allowed his men to continue the assault and eventually take San Juan Hill.

Since they heavily outnumbered their opponents, historians believe that American victory was inevitable at San Juan, and the war on the whole, but that wasn’t public opinion at the time. The Rough Rider’s story quickly made the papers, and Roosevelt became a national hero for winning the war.

Roosevelt was quickly recommended for the Medal of Honor for his charge of San Juan Hill, and in a letter he wrote “I am entitled to the Medal of Honor and I want it”. However, the war department never acted on the recommendation. There are two possible explanations for this, the first being that the department had a bias against volunteers. The second explanation is a grudge held by the Secretary of War. After the war ended, the Secretary of War, with the support of the McKinley Administrations, was reluctant to allow the return of American soldiers who had contracted Yellow Fever. Knowing that their condition would only worsen if they were not returned home, Roosevelt publicly shared his disapproval. The McKinley Administration came off as cold and uncaring to the American public, and they immediately had to reverse course and begin welcoming sick soldiers back home. This embarrassment to the Secretary of War left him with a grudge against Roosevelt, and many think this kept him from approving Roosevelt’s Medal of Honor recommendation.

Roosevelt’s Medal of Honor recommendation was finally approved by President Bill Clinton. On January 16th 2001, one hundred and three years after the battle, Roosevelt was posthumously awarded the Medal of Honor for his charge of San Juan Hill. The award was accepted by Roosevelt’s great grandson. That day, Roosevelt and his son became the second father and son in history to each receive a Medal of Honor. Roosevelt also became the only person in history to receive both the Medal of Honor and the Nobel Peace Prize.

The Medal of Honor podcast is a production of Evergreen Podcasts.

Nathan Corson is our executive producer and mixing engineer, Declan Rohrs is our associate producer, scriptwriter, and recording engineer, and I’m Ken Harbaugh.

We are proud to support the National Medal of Honor Museum. To learn more, and to support their mission, go to mohmuseum.org. Thanks for listening.