Questions to Ask Theodore Roosevelt
For a student writing an imagined interview with Theodore Roosevelt for a history project, and for anyone who would pick him as their dinner guest. The questions follow his life in order: the asthmatic boy and the Badlands, the climb from police commissioner to the Rough Riders and the presidency, the White House years, conservation, the 1912 campaign and what came after, then his family and what he would make of today. Each note says where the record gives you an answer, what a believable reply sounds like and where he would most likely dodge.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Early years
You were a sickly boy with asthma so bad you often slept sitting up. What did those nights teach you?
Why ask it
He remembered his father carrying him around the room during attacks, and a good answer starts there and not in the gym. Ask it first, because nearly everything he later preached about the strenuous life is an argument with that small boy.
Your father told you that you had the mind but not the body, and that you must make your body. Did you ever feel the job was finished?
Why ask it
The line reaches us through his sister's memory, so quote it as remembered and not as recorded. The believable answer is no: he was still boxing, rowing and riding hard as president, which looks like a task he never considered done.
At six you watched Lincoln's funeral procession from a window in New York. Do you remember it, or only the photograph?
Why ask it
A photograph of the procession shows two small figures at a window of his grandfather's house, identified as Theodore and his brother Elliott. It works as a question about memory itself: let him admit which parts were told to him afterward.
As a small boy you started a 'Roosevelt Museum of Natural History' in your bedroom with a seal's skull from a Broadway market. Why did you give up on becoming a scientist?
Why ask it
He entered Harvard meaning to be a naturalist, and his autobiography blames the college's taste for microscope work over field study for turning him away. Keep the answer for the conservation questions, because the boy who skinned and labeled birds is the president who later set aside reserves for them.
On February 14, 1884 your mother and your wife Alice died in the same house within hours. Why did you almost never speak of Alice again?
Why ask it
His diary for that day holds a large X and one sentence about the light going out of his life, and his autobiography leaves her out entirely. Do not write him a flowing answer. A short reply or a change of subject is truer to the record than a speech about grief.
You arrived in the Dakota Badlands as a New Yorker in glasses. What did the cowboys make of you, and how did you change their minds?
Why ask it
The stories he told on himself are the material: being mocked as Four Eyes, the barroom bully he knocked down, the long days in the saddle on roundups. Check which of them rest only on his own telling, since he was the chief publicist of his Western years.
You chased three boat thieves down an icy river for days and read Tolstoy while you guarded them. Why not just let the boat go?
Why ask it
It happened on the Little Missouri in 1886, when he was a deputy sheriff, and his own account is about law in a place that had very little of it. Follow up by asking whether the man with a novel in his pocket was also enjoying the story he would get to tell.
The winter of 1886 to 1887 killed much of your herd and a large part of your investment. Was the ranch a failure?
Why ask it
In money, yes: he lost a large share of what he had put in. Have him set the ledger beside what he said the Badlands gave him, including his claim that he would never have been president without those years.
Rise
As a New York police commissioner you walked the streets after midnight to catch officers off their beats. Was that police work or theater?
Why ask it
Reporters went along, Jacob Riis among them, and the papers loved it. The honest reply is both, and that blend of real reform and good copy is a pattern to point out before the interview reaches the White House.
As assistant secretary of the Navy you cabled orders to Commodore Dewey on an afternoon when your boss was out of the office. Did you overstep?
Why ask it
Secretary Long grumbled about that afternoon in his diary and then let the order to Dewey stand. This is the first clear case of Roosevelt acting first and explaining later, so keep the answer in mind for the Panama question further down.
Your father paid a substitute to serve for him in the Civil War. How much of your own eagerness to fight came from that?
Why ask it
Biographers raise this often and he never wrote it down himself, so in a project present it as their reading and not his confession. A reply that turns straight to praise of his father, whom he called the best man he ever knew, is probably the realistic one.
You left a desk in Washington for a war in Cuba at thirty-nine, with six children at home. Who tried to talk you out of it?
Why ask it
Nearly everyone did, and his wife Edith had been seriously ill that spring. A worrying answer treats the choice as obvious. A better one admits what he was prepared to leave behind in order to go.
The Rough Riders mixed cowboys, miners and Ivy League athletes. How did you turn them into one regiment in a few weeks?
Why ask it
This one suits younger students, and it has a researchable answer in the training camp at San Antonio under Leonard Wood, who was the regiment's colonel at the start. Ask what the polo players and the ranch hands thought of each other.
You called the charge up Kettle Hill the great day of your life. What do you say to the Black regulars of the 9th and 10th Cavalry who were on that hill too?
Why ask it
The Buffalo Soldiers fought beside his men on July 1, 1898. He praised them at first and later wrote slightingly of them in a magazine account that veterans disputed in print. Without this question the charge becomes a one-man story, so do not let him skip it.
After the fighting, with fever spreading through the army in Cuba, you and your fellow officers signed a letter demanding the men be brought home. What did that letter cost you?
Why ask it
The round robin letter leaked to the press and embarrassed the War Department. Many accounts tie it to the long wait for his Medal of Honor, awarded only in 2001, so ask whether he would sooner have had the medal or the ships home.
Your 1899 speech in Chicago on the strenuous life is remembered as a sermon on hard work, yet much of it argues for holding the Philippines. Was it about character or about empire?
Why ask it
He gave it to the Hamilton Club that April, while American troops were fighting Filipinos who wanted independence. To him a nation's duty and a man's were one subject, so let him refuse the choice, and bring the answer back when the interview reaches the big stick.
New York's party boss wanted you out of the governor's chair and into the vice presidency. Did you know you were being shelved?
Why ask it
He knew, and said so in letters, which makes this easy to source. What needs explaining is why he took a job he considered a dead end, and whether 1904 was already on his mind.
You were on a mountain in the Adirondacks when word came that President McKinley was dying. What went through your mind on the night ride down?
Why ask it
He had been told McKinley was recovering, went hiking on Mount Marcy, then raced by wagon over dark roads to reach a train. Expect him to speak of duty. Press once for the less tidy feeling of gaining the office through a murder.
You took the oath in a friend's house in Buffalo at forty-two and promised to continue McKinley's policies. How long did you mean it?
Why ask it
He is still the youngest person to have become president, and the promise calmed the markets and his party. Set the answer against what happened within six months, when his government sued a railroad combination that McKinley's allies had no quarrel with.
President
You sued Northern Securities without warning J.P. Morgan. What did he say when he came to see you?
Why ask it
Morgan is reported to have suggested that their men could meet and fix it up, as if the president were a rival operator. Build the reply around why that sentence bothered him more than the merger did, because it is the whole argument about who governs.
People call you the trust buster, yet you said there were good trusts and bad ones. How did you tell them apart?
Why ask it
Here a student can show real understanding. He wanted big business regulated more than broken up, and his successor Taft filed more antitrust suits than he did. A reply that only boasts about smashing monopolies is the cartoon version.
In the 1902 coal strike you called owners and miners to the same table and let it be known the Army might run the mines. Would you really have done it?
Why ask it
He told people afterward that he would have. Presidents before him had sent troops against strikers, and he stepped in as a referee. The follow-up is by what authority, because he did not much care, and that is a fair worry about him.
What exactly did you mean by a square deal, and who was left out of it?
Why ask it
The phrase grew out of the coal strike and meant fair treatment for labor and capital alike. The second half is the test: have him answer for Black Americans, Native nations and Filipinos, and see whether the square holds.
You read The Jungle and signed meat inspection and pure food laws, yet you called writers like Upton Sinclair muckrakers. Ally or nuisance?
Why ask it
Both, and he would say so cheerfully. For a project the 1906 laws make an easy cause and effect story. Keep in the detail that he sent his own investigators to the Chicago packing houses before he trusted the novel.
About a month into your presidency you had Booker T. Washington to dinner at the White House. Why did you never invite him to dine again?
Why ask it
The dinner in October 1901 set off furious attacks in Southern newspapers, and afterward he went on consulting Washington but not at his table. If he blames the reaction and stops there, push him on what he owed his guest.
In 1906 you discharged 167 Black soldiers after a shooting in Brownsville, Texas, with no trial. The Army cleared them in 1972. What would you say to them now?
Why ask it
His admirers most often leave this decision out, and he never backed down from it in his lifetime. If you are writing his reply, do not hand him an apology he never made. Let the interviewer state what the later investigation found.
When Colombia's senate turned down your canal treaty, a revolution broke out in Panama with an American warship offshore. Did you take the canal zone?
Why ask it
Years later he boasted that he took it and left Congress to debate, and he also insisted every step was proper. Make him choose between the two. The United States paid Colombia $25 million after his death, a fact that belongs in the interviewer's mouth.
You went to Panama in 1906 and sat at the controls of a steam shovel. Why did you need to see the digging yourself?
Why ask it
No sitting president had left the country before, and the photograph did as much for the canal's support as any report. It is lighter than the question before it, and it shows how well he understood a picture.
You liked the saying about speaking softly and carrying a big stick. When did you actually speak softly?
Why ask it
The best evidence for the soft half is 1905, when he brought Russia and Japan to terms at Portsmouth and won the Nobel Peace Prize for it. The stick is easier to find: the battleship fleet he sent around the world and his claim of a right to police the Caribbean, so have him weigh the two.
In 1905 you called college football men to the White House because players were being killed on the field. Why was that a president's business?
Why ask it
Try it on students who play a sport. He loved the game and wanted it kept, and the rule changes that followed led toward the body that became the NCAA. Then ask what he would make of today's arguments over safety.
On election night in 1904 you announced you would not run again. Was that the worst mistake of your career?
Why ask it
He is reported to have said later that he would give a great deal to take the statement back. It matters for the plot. That pledge is why Taft was president in 1909 and why 1912 happened at all, so place it before the questions on the third-party run.
You said no president had ever enjoyed the job as much as you did. Which single act of those seven and a half years are you proudest of?
Why ask it
His autobiography calls the canal by far the most important thing he did in foreign affairs. A student can argue with him here: put the forests or the peace at Portsmouth to him and make him defend the choice.
Conservation
You protected around 230 million acres of public land. Which single place are you gladdest you saved?
Why ask it
The acreage is the National Park Service's figure, so cite it that way. For his reply pick one place and research it properly: Pelican Island, Crater Lake, Devils Tower and the Grand Canyon each have their own story of who wanted the land for something else.
You camped in Yosemite with John Muir in 1903 and woke under snow. What did he ask you for, and what did you refuse him?
Why ask it
Muir wanted wild places left alone, while Roosevelt's forester Gifford Pinchot wanted them managed for use. The fight over damming Hetch Hetchy Valley is where the split shows. Get him to admit that he sided with Pinchot more often than the campfire story suggests.
You used the Antiquities Act, written with ruins and relics in mind, to protect the Grand Canyon. Was that stretching the law?
Why ask it
It was, and presidents of both parties have since followed the same reading. Students can argue either side: a canyon kept from mining claims, or one man deciding what Congress had not.
In 1907 Congress moved to stop you creating forest reserves in six Western states, and you named millions of acres before signing the bill. Fair play?
Why ask it
The midnight forests show him at his most gleeful, and he tells the story with relish in his autobiography. Give the furious Western senators a line in your interview too. Their complaint about a distant government locking up local land is still heard.
You hunted big game on three continents and protected more wild land than any president before you. How do those fit together?
Why ask it
To him they fit without strain: hunters, he argued, were the people with a reason to keep game and its habitat from vanishing. Younger students tend to find this the hardest thing to accept about him, which makes it a strong question for discussion.
The parks and forests you set aside were homelands of Native nations. Did you consider that anyone was being pushed out?
Why ask it
His Western books speak of Native people harshly, and little in his writing suggests he saw a conflict here. Do not soften that in his voice. Pair the answer with a look at whose land one particular park had been, which is a research task of its own.
1912 and after
You chose William Howard Taft as your successor and four years later ran against him. What did he do that you could not forgive?
Why ask it
The usual list is the firing of Pinchot, the tariff and an antitrust suit that implied Roosevelt had been fooled while president. An answer that is all policy should make you suspicious. The friendship was real and Taft is said to have wept over the break, so leave room for the personal hurt.
You left the White House at fifty and came home from Africa and Europe to cheering crowds. Could you ever have stayed retired?
Why ask it
His daughter Alice is credited with the joke that he wanted to be the bride at every wedding and the corpse at every funeral. A reply claiming that duty alone dragged him back deserves a raised eyebrow from the interviewer.
The Bull Moose platform called for votes for women, an end to child labor and insurance for the old and the sick. Had you changed, or had the country?
Why ask it
Set the 1912 platform beside what he did as president and the distance is plain. He moved a long way toward reform after leaving office. It makes good material for a timeline, since much of that list became law decades later under other presidents.
In Milwaukee you were shot in the chest and then spoke for more than an hour with the bullet still in you. Courage or showmanship?
Why ask it
The folded speech and a steel eyeglass case in his breast pocket slowed the bullet, and he opened by telling the crowd it takes more than that to kill a bull moose. Everyone at a dinner table wants this story. Have him also say what the doctors thought of his decision.
You split the Republican vote in 1912 and Woodrow Wilson won. Was the run worth it?
Why ask it
He finished second, ahead of the sitting president, and no third-party candidate has placed that high since. Expect a defense on principle. The harder follow-up is that he handed the office to a man he came to despise.
On the River of Doubt in Brazil you were so sick you told the others to go on without you. What made you get up?
Why ask it
The expedition with Cândido Rondon nearly killed him with fever and an infected leg, and his son Kermit refused to leave him. Ask why a former president in his mid-fifties was on an unmapped river at all. He called it his last chance to be a boy.
In 1917 you asked President Wilson to let you raise a division and lead it to France, and he said no. Was he right?
Why ask it
Wilson's generals wanted a drafted, professional army and not a famous volunteer of fifty-eight in poor health. Most historians side with Wilson. Roosevelt never did, and the refusal sharpened a hatred that colors nearly everything from his last two years.
All four of your sons went to the war you had urged, and Quentin, the youngest, was shot down in 1918. Did that change what you believed about the glory of battle?
Why ask it
Ask this gently and near the end. In public he held to his view, those close to him said he was never the same, and he died about six months later. The realistic answer is one proud sentence followed by a silence.
Family and today
Your children rode a pony in the White House elevator and your daughter Alice carried a snake in her purse. Were you a strict father or one of the gang?
Why ask it
The pony, Algonquin, was smuggled upstairs to cheer up a sick Archie, and the picture letters he wrote his children are in print. It makes a light opener for the dinner-guest game, and his reported remark that he could run the country or attend to Alice, but not both, does half the work.
Edith had known you since you were both small children in New York. What did she tell you that nobody else dared to?
Why ask it
They married in London in December 1886, less than three years after Alice died, and by family accounts she kept the household's money and gave the blunter verdicts on the people around him. Decide before you write whether your interviewer mentions the timing, since he would not raise it himself.
You disliked being called Teddy, and then a toy bear was named after you. What do you make of that?
Why ask it
The bear goes back to a 1902 hunt in Mississippi, where he refused to shoot an animal that had been tied up for him, and a newspaper cartoon did the rest. Younger children can trace the whole chain from hunt to cartoon to toy shop in an afternoon.
You were said to read a book a day and you wrote more than thirty of your own. What are you reading now, and what should a sixteen-year-old read?
Why ask it
Let the reply run long and jump between subjects: naval history, birds, poetry, a novel he argues with. For a written interview, take the titles from letters where he recommended books to friends and do not guess at modern ones.
Your face is on Mount Rushmore beside Washington, Jefferson and Lincoln. Do you belong there?
Why ask it
He would say yes without blushing, so the fun is in his reasons. A student can use the reply as a conclusion: which of his acts earn the place, and which would the other three have questioned?
The museum your father helped found took down the statue of you on horseback at its entrance. Do you understand why?
Why ask it
The statue showed him mounted, with a Native American man and an African man on foot at his sides, and the objection was to that arrangement more than to him. Members of his own family supported the move. Write him as neither outraged nor contrite, and have him ask what the sculptor meant and what visitors saw.
You called the presidency a bully pulpit and kept reporters close. What would you do with a phone that reaches millions in a second?
Why ask it
Bully meant splendid in his slang, not threatening, and that needs a footnote. He courted the press daily, so an answer in which he ignores modern media is not believable. One in which he posts far too often is.
Which of today's giant companies would you take to court first, and what would you want to know before deciding?
Why ask it
Keep him from naming a company on instinct. His own test was conduct and not size, so the reply should ask what the firm has done to its competitors and customers. That holds the interview to history and stops it becoming the writer's opinion in a mustache.
The national parks now draw crowds that line up at the gates. Is that the success you wanted or the problem you feared?
Why ask it
At the Grand Canyon he told the country to leave it as it is, and he also wanted ordinary citizens to see such places. Both wishes are on the record, so this hands him a real dilemma and not a setup for applause.
What would you say to someone who has only met your man in the arena passage on a poster?
Why ask it
The passage comes from Citizenship in a Republic, a speech he gave in Paris in 1910, and the rest of it is about what a republic needs from its ordinary citizens. Send students to the full text. Ending on what the poster leaves out makes a strong close.
You get one question back. What do you most want to know about the America of today?
Why ask it
Turn the table at the very end. Whatever he asks about first, whether the Navy, the forests, the canal or his own grandchildren, tells the audience which of his causes the writer thinks mattered most to him.
Writing and running an imagined interview with Theodore Roosevelt
Practical guidance for the conversation itself
Before you write a word of his
Decide which Roosevelt is in the chair
The president of 1905 is confident about almost everything. The man of late 1918 has lost an election, nearly died in Brazil and buried a son. Pick the year your interview takes place and write it on the first line, because the same question gets a different answer from each of them. If you want the questions about today, say plainly that he has been brought forward and briefed.
Choose eight to twelve, not the whole list
A project that asks everything answers nothing well. Take two from his early years, then build around the part of his life your assignment is about: the trusts, the parks, the canal or 1912. Finish with one from the last group so the piece has an ending.
Keep the order of his life
The groups run the way his life did, and later answers lean on earlier ones. The Dewey cable sets up Panama, the 1904 pledge sets up the break with Taft, and the boy with asthma sets up nearly everything. Shuffle them and those echoes are lost.
Put the facts in the question
Let the interviewer carry the dates, names and numbers, as the questions here do. Then his reply can be about reasons and feelings, which is where the imagining belongs, and a reader can tell at a glance what is record and what is your invention.
Making the answers sound like him
Fast, certain and fond of a story
He spoke in bursts, hit his words hard and moved from a law to a bird to a boxing match in one breath. Recordings of his 1912 speeches survive and are worth two minutes of listening. Write short, emphatic sentences, let him interrupt himself with an anecdote, and use 'bully' or 'delighted' once at most. A catchphrase in every reply turns him into a mascot.
Borrow his real words and mark them
His 1913 autobiography, his letters to his children and his major speeches are all in print and free to read online. Where he answered your question himself, quote a sentence and show that it is a quotation. Where you are inventing, stay close to positions he actually took. A reader should never have to wonder which is which.
Let him dodge where he really did
He would talk for an hour about Kettle Hill and say nothing about his first wife. On Brownsville he dug in. An interview in which he opens up evenly on everything is less true than one in which he changes the subject twice and the interviewer notices.
Check a famous line before you use it
Several of the best Roosevelt stories come from someone else's memory years later: the father's challenge, Morgan's offer, the wish to take back the 1904 pledge. They are fine to use with 'he is said to have' in front of them. Presenting a remembered line as a transcript is the quickest way to lose points on sourcing.
Where these interviews go wrong
The cartoon Teddy
Teeth, glasses, a shout and a bear. It is easy to write and it explains nothing. If every answer could be read aloud in a booming voice with no loss, add the man who wrote natural history, grieved in private and read novels on a cattle roundup.
The apology he never made
On race, on empire and on the people moved off the land he protected, his views were common for a powerful man of his time and harsh by any later measure. Do not rewrite him as sorry. Let the interviewer supply what happened afterward, let him answer as he would have, and let the reader judge the distance.
Your opinions in his mustache
The questions about today are the easiest place to make him agree with you. Test each modern answer against something he did: his rule for trusts, his use of the press, his fights with Congress over land. If you cannot name the act behind the answer, the opinion is yours and it should go.
All hero or all villain
A good interview has at least one question he enjoys and one he would sooner not hear. If your draft has only the charge, the parks and the bullet in Milwaukee, add Brownsville or Panama. If it has only the hard ones, add the pony in the elevator, because the charm is part of how he got his way.
For the dinner-guest game
One question each, and say why
When the table picks Roosevelt as its guest, give every player a single question from the list and a sentence on why they chose it. The reasons are usually more interesting than the questions, and they show who came for the adventure and who came for the argument.
Answer for him, then argue
Have one person reply in his voice and let the others challenge anything that does not sound like him. Nobody needs to be an expert. Somebody will look up whether the bullet really stayed in his chest, and the game has done its work.
Good picks for a mixed table
The boat thieves, the Milwaukee speech, the teddy bear, the pony and the River of Doubt work with any age. Save the questions on Brownsville, Panama and Quentin for a table that wants a real conversation, and give them time.