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Questions to ask Theodore Roosevelt

9 min read

Theodore Roosevelt (1858 to 1919) had more jobs than most people have hobbies: rancher, police commissioner, colonel of the Rough Riders, the youngest President, Nobel Peace Prize winner and Amazon explorer. Good interview questions take him through those jobs and ask about his conservation record, the trusts, the Panama Canal, the Brownsville affair and the night he was shot in 1912. Here are 26 questions, what the record says and answers from his own writing.

Roosevelt's jobs at a glance

Pick one row for a short interview or walk through them all for a report. A wax museum Roosevelt is usually the Rough Rider of 1898 or the President of about 1905.

YearsJobOne fact to build a question on
1882 to 1884New York State AssemblyElected at 23, the youngest member
1884 to 1886Cattle rancher, Dakota TerritoryWent west after his wife and mother died on the same day
1895 to 1897President of the New York City Police BoardWalked the streets at night checking on officers
1897 to 1898Assistant Secretary of the NavyPrepared the fleet before the war with Spain
1898Lieutenant colonel, then colonel, Rough RidersLed the charge up Kettle Hill on 1 July 1898
1899 to 1900Governor of New YorkParty bosses pushed him into the vice presidency to be rid of him
1901 to 190926th PresidentTook office at 42 on 14 September 1901
1912Progressive (Bull Moose) candidateShot in Milwaukee and still gave his speech
1913 to 1914Explorer in BrazilMapped the River of Doubt and nearly died

Questions about childhood, loss and the Badlands

  • 1. You were a sick child with bad asthma. How did you build yourself up?
  • 2. Why did you collect and stuff birds and animals as a boy?
  • 3. On 14 February 1884 your mother and your wife Alice died in the same house. How did you go on?
  • 4. What did ranching in Dakota teach you that Harvard did not?

What the record says: his Autobiography (1913) describes the asthma, the gym his father set up at home and the boxing lessons. He gave his boyhood specimens to the Smithsonian and the American Museum of Natural History, which his father helped found. His diary for 14 February 1884 has a large cross and the words “The light has gone out of my life.” He wrote almost nothing about Alice afterwards, so let him be brief.

Questions about the war of 1898

  • 5. Why did you resign from the Navy Department to fight in Cuba?
  • 6. Who were the Rough Riders, and how did you pick them?
  • 7. What happened on Kettle Hill on 1 July 1898?
  • 8. Black regiments fought beside you. Why did your later account play down their part?

What the record says: the 1st US Volunteer Cavalry mixed cowboys, Native Americans, miners and Ivy League athletes. Roosevelt's book The Rough Riders (1899) tells the story his way. The 9th and 10th Cavalry, Black regular regiments, were in the same attack on the San Juan heights. Historians note that his early praise of them was later replaced by criticism that their officers and the men themselves rejected.

Questions about the presidency

  • 9. You became President because William McKinley was assassinated. How did that feel?
  • 10. Why did you invite Booker T. Washington to dinner at the White House in October 1901, and what happened next?
  • 11. Why did you sue the Northern Securities railroad company in 1902?
  • 12. In the 1902 coal strike you threatened to send in the army to run the mines. Why take the miners' side?
  • 13. What did you mean by a “Square Deal”?
  • 14. How did Upton Sinclair's The Jungle lead to the meat inspection and pure food laws of 1906?
  • 15. How did you end the war between Russia and Japan, and what did winning the Nobel Prize mean to you?
  • 16. Why did you send the navy's battleships around the world in 1907?

What the record says: the Booker T. Washington dinner of 16 October 1901 caused a storm of racist abuse in the Southern press, and he never repeated it. The Supreme Court upheld the Northern Securities breakup in 1904. The Pure Food and Drug Act and Meat Inspection Act were both signed on 30 June 1906. He mediated the Treaty of Portsmouth (September 1905) and in 1906 became the first American to win a Nobel Prize. The “Great White Fleet” sailed from December 1907 to February 1909.

Questions about conservation

  • 17. Why did you believe the government had to protect forests and wildlife?
  • 18. You used the Antiquities Act to protect Devils Tower and the Grand Canyon. Why not wait for Congress?
  • 19. You were a hunter and a conservationist. How did you square those?
  • 20. Is the teddy bear story true?

What the record says: with his chief forester Gifford Pinchot he put roughly 230 million acres under federal protection, including 150 national forests, 51 federal bird reservations, 5 national parks and 18 national monuments. He signed the Antiquities Act on 8 June 1906 and named Devils Tower the first national monument that September. The teddy bear story is true in outline: in November 1902 in Mississippi he refused to shoot a bear that had been tied up, and a cartoon by Clifford Berryman made it famous. His 1908 Conference of Governors at the White House set out conservation as a national duty.

Hard questions on race and empire

  • 21. In 1903 you backed Panama's break from Colombia to get the canal zone. Was that fair to Colombia?
  • 22. In 1906 you dismissed 167 Black soldiers after a shooting in Brownsville, Texas, without a trial. Why?
  • 23. You wrote in The Winning of the West that settlers were right to take Native land. Do you stand by that?

What the record says: American warships prevented Colombian troops from stopping Panama's revolt in November 1903, and the canal treaty followed within weeks; the United States paid Colombia 25 million dollars in 1921. In the Brownsville affair the soldiers of the 25th Infantry denied involvement; the Army reversed the discharges in 1972. His views on race were those of many educated men of his time, and he expressed them openly. Let your Roosevelt defend himself in his own terms, and add a sentence in your own voice giving the criticism.

Questions about the last campaigns

  • 24. Why did you break with your friend William Howard Taft and run against him in 1912?
  • 25. You were shot in the chest in Milwaukee on 14 October 1912 and spoke for over an hour. Why not go to hospital?
  • 26. Your son Quentin, a pilot, was killed in France in July 1918. What did you write about it?

What the record says: the bullet was slowed by his folded 50-page speech and his metal spectacle case; it stayed in his body for the rest of his life. He opened by telling the crowd he had just been shot, but that it takes more than that to kill a Bull Moose. Quentin was shot down on 14 July 1918. Roosevelt died in his sleep at Sagamore Hill on 6 January 1919, aged 60.

Sample answers in his own words

For question 1 or 4, on fear and courage:

“There were all kinds of things of which I was afraid at first, ranging from grizzly bears to “mean” horses and gun-fighters; but by acting as if I was not afraid I gradually ceased to be afraid.”
Theodore Roosevelt: An Autobiography (1913)

For question 9:

“It is a dreadful thing to come into the Presidency in this way; but it would be far worse to be morbid about it.”
Letter written in September 1901, soon after McKinley's death

For question 13 or 22, from a speech to veterans:

“A man who is good enough to shed his blood for his country is good enough to be given a square deal afterwards.”
Speech at Springfield, Illinois, 4 July 1903

For a question about how to live:

“Hit the line hard; don't foul and don't shirk, but hit the line hard!”
“The American Boy”, St. Nicholas magazine, May 1900

For a question about critics, his Paris speech “Citizenship in a Republic” (23 April 1910) begins its best-known passage: “It is not the critic who counts.” The credit, he went on, belongs to the man in the arena.

Things he could not answer

  • His face on Mount Rushmore was carved between 1927 and 1941, after his death.
  • If you set the interview in 1905, he does not know about the 1912 shooting, the Amazon or Quentin's death.
  • He knew his fifth cousin Franklin as a young politician. He died fourteen years before the New Deal; see our questions to ask Franklin D. Roosevelt.
  • Ask about conservation in his time, not about modern climate policy.

Practise with a talkative President

Roosevelt talked fast and interrupted, so a live rehearsal helps you keep control of your interview. You can try it with an AI recreation of Theodore Roosevelt on Yuga, by voice or text. It draws on his books, speeches and the historical record, but it is a recreation and can be wrong. Quote his own writings in your work.

Where to read Roosevelt's words

  • Theodore Roosevelt: An Autobiography (1913) and The Strenuous Life (1900), free on Project Gutenberg.
  • The Theodore Roosevelt Center at Dickinson State University, which is digitising his papers and letters.
  • The Theodore Roosevelt Papers at the Library of Congress, the largest collection of his manuscripts.
  • NobelPrize.org has the facts of his 1906 Peace Prize.
  • The National Park Service runs his birthplace in Manhattan, Sagamore Hill on Long Island and the Theodore Roosevelt Inaugural site in Buffalo.

For a whole-class version of this, see our wax museum project guide.

Questions people ask

What are good questions to ask Theodore Roosevelt?
Ask how he overcame childhood asthma, why he went west after the deaths of 14 February 1884, what happened on Kettle Hill in 1898, why he sued Northern Securities, how he chose land to protect, why he took the Panama Canal Zone, why he dismissed the Brownsville soldiers and how he gave a speech after being shot.
How much land did Theodore Roosevelt protect?
About 230 million acres of public land. As President from 1901 to 1909 he created or expanded 150 national forests, 51 federal bird reservations, 5 national parks and 18 national monuments, using the Antiquities Act of 1906 for many of the monuments, including Devils Tower and the Grand Canyon.
Why did Theodore Roosevelt win the Nobel Peace Prize?
For mediating the end of the Russo-Japanese War. He brought the two sides to talks at Portsmouth, New Hampshire, where they signed a treaty in September 1905. He received the 1906 Nobel Peace Prize, the first Nobel Prize won by an American.
Is the teddy bear named after Theodore Roosevelt?
Yes. In November 1902, on a hunt in Mississippi, guides tied up a bear for him to shoot and he refused. A cartoon by Clifford Berryman in the Washington Post spread the story, and toy makers began selling “Teddy's bears”. He disliked the nickname Teddy.

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