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Theodore Roosevelt

Awarded the Medal of Honor

In office: September 14, 1901 March 4, 1909

Born: October 27, 1858, New York, New York
Died: January 6, 1919 (age 60), Oyster Bay, New York

Theodore RooseveltTheodore Roosevelt, also known as T.R., and to the public (but never to friends and intimates) as Teddy, was the twenty-sixth President of the United States. A leader of the Republican Party and of the Progressive Party, he was a Governor of New York and a professional historian, naturalist, explorer, hunter, author, and soldier. 

He is most famous for his personality: his energy, his vast range of interests and achievements, his model of masculinity, and his "cowboy" image. Originating from a story from one of Roosevelt's hunting expeditions, Teddy bears are named after him. Roosevelt was posthumously awarded the Medal of Honor in 2001 for his actions.

1. In 1880, what college did Roosevelt graduate from?

  • Harvard
  • Yale
  • Princeton

2. On February 14, 1884, Alice Hathaway Lee was the first wife of Theodore Roosevelt and mother of their child, Alice. Roosevelt's wife, Alice died of an undiagnosed (since it was camouflaged by her pregnancy) case of kidney failure called, in those days, Bright's disease at 2 pm two days after Alice Lee was born. Who died of typhoid fever in the same house, on the same day, at 3 am, some eleven hours earlier?

  • Sir Andrew Jerome (British visitor)
  • Franklin K. Roosevelt (Roosevelt's 2nd cousin)
  • Mittie Bulloch (Roosevelt's mother)

3. While working on a tough project aimed at hunting down a group of relentless horse thieves, Roosevelt came across the famous Deadwood Sheriff. The two would remain friends for life. Who was the Deadwood Sheriff?

  • Wild Bill Hickock
  • Seth Bullock
  • John Anderson

4. In 1895, Roosevelt became president of the what board of New York City Commissioners?

  • Police
  • Fire
  • Legislative

5. In 1897, what post did President William McKinley appointed Roosevelt to?

  • Assistant Secretary of the Navy
  • Secretary of War
  • Secretary of the Interior

6. Upon the 1898 Declaration of War launching the Spanish-American War, Roosevelt resigned from the Navy Department. With the aid of U.S. Army Colonel Leonard Wood, Roosevelt found volunteers from cowboys from the Western territories to Ivy League friends from New York, forming what the newspapers called them the "Rough Riders." What was the Rough Riders official name?

  • First U.S. Volunteer Cavalry Regiment
  • The Volunteer Regiment from the West
  • 10th Cavalry Regiment

7. Under his leadership, the Rough Riders became famous for dual charges up Kettle Hill and San Juan Hill on July 1, 1898 (the battle was named after the latter "hill," which was the shoulder of a ridge known as San Juan Heights). Out of all the Rough Riders, Roosevelt was the only one with a horse, and used it to ride back and forth between rifle pits at the forefront of the advance up Kettle Hill; an advance which he urged in absence of any orders from superiors. However, he was forced to walk up the last part of Kettle Hill on foot, due to barbed wire entanglement and after his horse, Little Texas, became tired.

  • Fact or Myth?

8. When was he awarded the Medal of Honor for San Juan Hill?

  • 1900
  • 1945
  • 2001

9. On January 6, 1919, Roosevelt died at Oyster Bay, preceded by a 2 1/2-month illness described as inflammatory rheumatism. What was the cause of death?

  • Horse riding accident
  • Coronary embolism
  • Auto accident

10. Where is Theodore Roosevelt buried?

  • Youngs Memorial Cemetery, Oyster Bay, New York
  • San Juan Hill Memorial Gardens, Oyster Bay, New York
  • Bulloch Family Cemetery. Roswell, Georgia


  • 1. Harvard
  • 2. Mittie Bulloch (Roosevelt's mother)
  • 3. Seth Bullock
  • 4. Police
  • 5. Assistant Secretary of the Navy
  • 6. First U.S. Volunteer Cavalry Regiment
  • 7. Fact
  • 8. 2001
  • 9. Coronary embolism
  • Angels on your pillow10. Youngs Memorial Cemetery, Oyster Bay, New York
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