History Vs. Podcast Episode 3: Theodore Roosevelt Vs. Tragedy


Mental Floss has a new podcast with iHeartRadio called History Vs., about how your favorite historical figures faced off against their greatest foes. Our first season is all about President Theodore Roosevelt. Subscribe on Apple Podcasts here, and for more TR content, visit the History Vs. site.

It’s July 16, 1918, and Theodore Roosevelt is at his Sagamore Hill home in Oyster Bay, New York, dictating correspondence to his secretary when there’s a knock at the door. It’s a reporter, who hands Roosevelt a telegram that reads: “WATCH SAGAMORE HILL IN EVENT OF…” Then it ends, the rest of the message edited out to protect it from prying eyes.

The message might be censored, but Roosevelt knows what it means. World War I is raging, and all four of his sons signed up to fight. Ted and Archie are injured, and Kermit isn’t in a dangerous area yet. That leaves Quentin, a 20-year-old fighter pilot warding off German planes over France.

Though he won’t get further confirmation for a few days, Roosevelt knows what has happened. He knows that he’s never going to see Quentin, his youngest and favorite son, again.

Roosevelt asks the reporter not to say anything to his wife, Edith. He continues to dictate letters. Soon he will be told Quentin is missing in action following a fierce aerial battle. It’s reported that Quentin faced off against an ace German pilot before being shot down.

General John Pershing writes to Roosevelt that they are holding out hope that Quentin landed. But there will be no happy ending. Newspapers are reporting that Quentin has died, and, on July 20, Roosevelt receives official word from President Woodrow Wilson confirming the news. The German government prints a horrific photograph of Quentin’s body next to his downed plane.

Publicly, Roosevelt is stoic as ever. Privately, he heads to his stable and embraces Quentin’s pony, his arms around the animal’s neck. “Poor Quentyquee,” he says, whispering Quentin’s nickname. “Poor Quentyquee.” A friend and future biographer would say of Roosevelt that “the old exuberance, the boy in him has died.”

From Mental Floss and iHeartRadio, this is History Vs., a podcast about how your favorite historical figures faced off against their greatest foes. I’m your host, Erin McCarthy, and this week’s episode is TR vs. Tragedy.

It’s not only that Roosevelt has lost a son, though that would be enough to send any parent into a state of anguish. It’s that Roosevelt has once again been confronted with unimaginable tragedy, the latest in a series of wounds that he’s endured throughout his life.

Those closest to him—his mother, his father, his first wife, his brother, and now his son—have all disappeared, most of them at a tragically early age. These moments reveal a great deal about Roosevelt’s character. They shaped his worldview. At times, they overwhelmed him. For TR, tragedy was a frequent visitor.

The first time it struck, he lost his idol. That was his father, Theodore Roosevelt Senior, who, when TR was a kid, implored his son not to be discouraged by his frequent asthma attacks and to pursue an active lifestyle. He loomed large in Roosevelt’s life as someone he aspired to be—stout, resourceful, determined. In Roosevelt’s words, his father was “the ideal man.” At Sagamore Hill, Roosevelt hung a portrait of his father that he could see whenever he sat down in his library.

Tyler Kuliberda: So Roosevelt said that his father was the best man he ever knew, and I certainly don't think that's just a son being kind to his father. I truly believe that he felt that way, that his father was the highest ideal that he could achieve. And I think a lot of his public service is aimed at righting the same wrongs, and righting societal ills that his father tried to right by philanthropy. Roosevelt attacks it from a different front, which is with government policy or government action.

That’s Tyler Kuliberda, the education technician at Sagamore Hill, which is now a National Historic Site.

Kuliberda: He’s looking at his father's portrait constantly, you would imagine, as he's working, whether it's president, or before the presidency or after the presidency his father is always there. His father is a philanthropist. He's incredibly wealthy. They're from one of the wealthiest families in New York City. And Roosevelt's father is his greatest inspiration. So TR’s father would give away a lot of their wealth to help found museums, orphanages, hospitals in New York.

Theodore Roosevelt Senior, or Thee, was born in 1831. Later, he pitched President Abraham Lincoln on a program where soldiers in the Civil War could send money back to their families.

Lincoln liked the idea, and Thee traveled around the front, signing soldiers up. His work was a kind gesture, but it wasn’t entirely borne out of generosity. There may have been a little guilt involved. Like many wealthy men of the era, he paid for a substitute to enter the Civil War so he wouldn’t have to enlist, which could have put him at war with his own wife. TR’s mother was from Roswell, Georgia, and her brothers were blockade runners—so things were probably a little tense at home.

Thee’s philanthropy wasn’t limited to war efforts. Often, he’d bring Roosevelt along on visits to orphanages and missions, a spark that likely led to his son’s desire to work in public service.

At the time, it wasn’t necessarily expected that someone wealthy would be so active with their family. That familial closeness was something Roosevelt would carry with him his entire life, spending as much time as he could with his relatives.

Kuliberda: This was in a time when if you were a wealthy family, if you were a wealthy man, you were not necessarily expected to be with your family other than at dinner every night, otherwise you were conducting business, or you were off doing whatever. Whereas, Roosevelt's father spent a lot of time with them, and they were actually considered an eccentric family, because of how much, you know, time they spent together, and I think how much they enjoyed each other’s company.

After a childhood spent traveling with his family and being privately tutored—because he was too sick for regular school—Roosevelt went off to Harvard in 1876. In his sophomore year, his father was nominated by President Rutherford B. Hayes as Collector of Customs in New York City. Hayes wanted to demonstrate he was committed to Civil Service Reform. The attention was taxing for Thee, who found himself a pawn between Republicans who backed Hayes and others who opposed reform. He was eventually rejected for the appointment.

The stress of the experience may have compounded his health issues. He had been struggling with pain and digestive problems brought on by an intestinal tumor, and it was progressing rapidly. Thee insisted that TR not be informed—he wanted his son to focus on his studies.

Eventually, Roosevelt was summoned back, and he rushed home from Harvard. But he was too late.

Thee died February 9, 1878 at the age of 46, just hours before TR made it home. Roosevelt was only a sophomore in college when his idol—the one his family called “Great Heart”—left his life forever.

On the day of his father’s funeral, Roosevelt wrote in his diary:

“I shall never forget these terrible three days; the hideous suspense of the ride on; the dull, inert sorrow, during which I felt as if I had been stunned, or as if part of my life had been taken away, and the two moments of sharp, bitter agony, when I kissed the dear dead face and realized that he would never again on this earth speak to me or greet me with his loving smile, and then when I heard the sound of the first clod dropping on the coffin holding the one I loved dearest on earth…I feel that if it were not for the certainty, that as he himself had so often said, ‘He is not dead but gone before,’ I should almost perish.”

Thee was, Roosevelt wrote, “Everything to me.”

Though Roosevelt would go on to experience the pain of personal loss several times over, never again would he articulate his grief in such plain language. It was as though his father’s passing stripped him of every bit of self-consciousness in his writing.

Those bare emotions continued pouring out. In his diary, Roosevelt struggled with a sense of guilt and a lack of self-worth. He was tortured by his helplessness, and the fact that he had been unable to assist or comfort his father in his last moments. He held his father in such regard that he felt unworthy of being his son.

“I often feel badly that such a wonderful man as Father should have had a son of so little worth as I am…How little use I am, or ever shall be in the world…I realize more and more every day that I am as much inferior to Father morally and mentally as physically.”

Roosevelt returned to Harvard, seemingly intent to prove himself wrong. He studied hard, exercised often, and spent summers rowing around Long Island Sound. He refused to allow his body or his mind to grow idle. Nature allowed him a way out of the darkness. He took steps forward.

Still, Roosevelt rarely acted without first comparing his plans to his father’s best judgment.

Kuliberda: He leaves his son this great sum of money, and Roosevelt uses that money to purchase the land around Sagamore Hill. He contracts with Lamb and Rich to build a Queen Anne style home, here. When he becomes president he realizes that he's about his father's age when his father had died, and he says, “I never weigh any heavy decision without considering what father would have done,” so his father is certainly his inspiration, it's his main role model. I don't think it's any coincidence why he hangs this portrait of him looking over him at his desk.

We’ll be right back.


Roosevelt’s mourning period for Thee lasted for months. Then, in October of 1878, just eight months following his father’s death, his life was unexpectedly brightened by the appearance of Alice Hathaway Lee.

The 17-year-old Alice was a cousin of one of Roosevelt’s Harvard friends, Richard Saltonstall. Roosevelt was immediately smitten with the strong, energetic Alice, who enjoyed physical activities like tennis and boating.

She seemed to blot out the gloom that had enveloped his life. He spent the next year trying to court her before she agreed to marry him. When they became engaged in January 1880, he exalted her.

“My sweet, pretty, pure queen, my laughing little love … how bewitchingly pretty she is! I can not help petting and caressing her all the time … I do not believe any man ever loved a woman more than I love her.”

She called him Teddy.

Kuliberda: I think he really fell for Alice. If you read letters between them, if you're an adult and you read them, and you're like, oh, boy, he fell really hard for her. He describes her as sunny, and after they're married he says that their relationship is too sacred for words, things like that, like really, really gushy, mushy stuff.

Roosevelt and Alice married on October 27, 1880, his 22nd birthday. While Roosevelt attended law school and worked on his book, The Naval War of 1812, Alice grew close to his mother, Mittie, whom the couple lived with in New York City, and got along well with his sisters, Anna—better known as Bamie or Bye—and Corrine. In 1881, Roosevelt was elected a state assemblyman. In 1883, Alice became pregnant with their first child. Soon, he hired an architectural firm to begin designing a house in Long Island for his expanding family.

Roosevelt intended to call the property Leeholm, after Alice’s maiden name.

Kuliberda: His intention with having a home here is to get out of New York City, like his family had before him. He’s going to raise his family here. He’s going to maintain a country home and be a country gentleman, and as well as somebody who lives in New York City. He buys the land after his father dies. He buys 155 acres. He starts buying in 1880, and then the house is built in 1884.

On February 13, 1884, Roosevelt was in Albany on business when he received a telegram with happy news. The day before, Alice had given birth to a healthy daughter, whom she had named Alice Lee Roosevelt.

But his joy was short-lived. Hours later, he received a second telegram. The telegram no longer exists, so we have no idea what it said, but we can assume from what happened next that it informed him that Alice was not in good health. She had Bright’s disease, a now-obsolete term for a condition that seriously damages the kidneys. Here’s Holly Frey, co-host of the Stuff You Missed in History Class podcast.

Frey: I have read various theories that in fact Teddy's wife, Alice, actually had kidney disease that was undiagnosed before her pregnancy, and that carrying a child exacerbated the problem and that's really what led to her passing so soon after Alice was born.

Alice was only barely conscious when he arrived. He held her in his arms through the early morning hours of February 14. As Alice tried to cling to life, Roosevelt was summoned to his mother’s room one floor below.

This time, he could at least be at her side, assuaging the guilt he had long felt over not being near his father’s. She passed away at 3 a.m.

At 2 p.m., Alice, just 22 years old, also died. She had been a mother for only two days.

Frey: He and his wife were living with his mother, so it was like his entire home life collapsed that day as he knew it. Which is really heartbreaking to think about. You know, essentially, to put it in kind of colloquial terms, like: two young kids who are starting their lives together and then it kind of all falls apart.

That same day, Roosevelt drew a large X in his diary and wrote “The light has gone out of my life.” He was just 25 years old.

Alice and Mittie were buried in Green-Wood Cemetery in a double funeral. Close friends of the family observed that Roosevelt appeared dazed and stunned, a state hardly typical of his pragmatic and focused disposition. Some even feared he might do something rash, taking total leave of his senses.

After the funeral, he wrote in his diary, “We spent three years of happiness greater and more unalloyed than [any] I have ever known fall to the lot of others … For joy or sorrow, my life has now been lived out.”

After that he rarely spoke of Alice again—not of their love or their good times together. Rather than confront his grief, Roosevelt seemed capable only of erasing it: Love letters and photographs were destroyed.

He wouldn’t even mention her in his autobiography. And after this double tragedy, he would lock himself, and his feelings, down for the most part. According to Kathleen Dalton, “Escape and flight from pain provided familiar devices to protect himself from his own strong emotions and from unpleasant facts he wanted to avoid.”

On February 18, he returned to Albany to finish out his term as Assemblyman, where he worked with frenetic energy. He left his daughter in the care of his sister, Bamie.

Frey: And Alice, named for her mother, he couldn't even bear to say her name so they started calling her Baby Lee. And he allegedly forbid everyone he knew in his family and social circle from saying the name Alice for quite some time, because it was just so upsetting to him.

McCarthy: Baby Alice looked a whole lot like her mother, too, so that must have been really difficult for him.

Frey: That's like a constant reminder of your heartache. And it's interesting, people often talk about the fact that he wrote precious little about his wife in his life, even when he worked with a biographer to write his life story. It was just too much of an emotional burden for him, pretty much for the rest of his life.

We’ll be right back.


Roosevelt soon left New York for the Dakota Territory and a ranch, where the solitude of the outdoors, and the hard work of ranching, allowed him to dull the pain. Once again, loss had devastated him, and once again, Roosevelt had to rebuild himself.

Roosevelt once said that he never would have been president if not for his time in the Dakotas. To find out why, we headed out there ourselves, to Theodore Roosevelt National Park, where we met with Eileen Andes, the Chief of Interpretation and Public Affairs at the park.

Andes: It's the experience of going out there and enjoying the peace and quiet and solitude that Roosevelt needed when he decided to make that his home ranch. And he wrote about listening to the birds and hearing the wind in the cottonwood trees and listening to the sounds of the river.

Roosevelt came to the Dakotas to hunt bison in 1883, and, while he was there, invested in the Maltese Cross cattle ranch. After two tragedies and a bumpy last term as a New York State Assemblyman, he intended to permanently relocate there. But the Maltese Cross didn’t fit all of his needs.

Andes: It was along the river, which was a thoroughfare and people kept stopping by and he wanted solitude. So somebody had told him about the Elkhorn Ranch site. So he got on his horse and rode the river bottom. It's 35 miles along the river bottom to the site. He liked it and he had two of his friends from Maine come and build that cabin for him. And when you go out there, you'll see, it's down in the river bottom, almost completely surrounded by bluffs. And there was nobody out there. He had no neighbors, nobody to just drop by. And that's really what he was looking for and really what he needed. And it's a beautiful, quiet place.

Roosevelt bought the rights to the Elkhorn property for $400. Quite a steal.

The house is no longer standing. After Roosevelt sold it off in 1898, it was picked over by 1901. But you can still drive out to the site, which is an hour and 15 minutes from the park’s visitors center, so Tyler, a producer on this podcast, and I do just that.

At first the roads are paved, but eventually, we turn off onto a red gravel road. The scientific name for that red gravel is clinker, and it’s not long before our white SUV is coated in a fine layer of red dust, like we went to Mars.

McCarthy: We are in the middle of nowhere. Like, literally in the middle of nowhere.

Eventually, we turn off the gravel road onto another, deeply rutted road.

McCarthy: Put that seatbelt on. We are... Genuinely rough-riding right now. So... gotta make sure you're all buckled up!

Tyler Klang: That's right.

McCarthy: So the road is surrounded by all of these bluffs. And some of them are really green... And some of them have a lot of erosion, and there's all these, like, yellow and white and gray layers.

GPS Voice: You have arrived.

Well, not quite. There’s still a bit of a walk from the parking lot out to the site. The path is surrounded by grass on either side, punctuated by cottonwood and juniper trees and yellow flowers and salsify plants that look kind of like huge dandelions when the seeds are ready to be blown off. Occasionally birds, and the moo of a cow, can be heard over the din of cicadas. Also, there are a lot of insects.

Klang: Did a butterfly attack you?

McCarthy: A butterfly just flew directly into my face!

Finally, we make it to the ranch site, which is cordoned off with barbed wire.

Klang: Do you want to give us a general description of where we are and what the area is like?

McCarthy: Yeah, so we are standing in between a whole bunch of stones on the grass, that vaguely form a little rectangle. Although, I guess it would be pretty big for a house out here. But yeah, we're just in this sort of flat area, and on one side is the Little Missouri River, and on the other side are all these bluffs that are like yellow, and gray, and white, with just a little bit of vegetation, but there are a lot of trees surrounding the site. It is really very peaceful. I can see why he liked it.

What was once here was a house 30 feet long and 60 feet wide, with seven foot high walls. Nearby were stables, a shed for cattle, a chicken house, and a blacksmith shop. On one side is a tall bluff, and on the other, through the trees, is the Little Missouri River—which one expert told me is 200 yards away from where it was in Roosevelt’s time.

Here’s how Roosevelt himself described the site:

“My home ranch house stands on the river brink. From the low, long veranda, shaded by leafy cotton-woods, one looks across sand bars and shallows to a strip of meadowland, behind which rises a line of sheer cliffs and grassy plateaus. This veranda is a pleasant place in the summer evenings when a cool breeze stirs along the river and blows in the faces of the tired men, who loll back in their rocking chairs, (what true American does not enjoy a rocking chair?), book in hand—though they do not often read the books, but rock gently to and fro, gazing sleepily out at the weird-looking buttes opposite, until their sharp outlines grow indistinct and purple in the afterglow of the sunset.”

McCarthy: Do you know why he named it Elkhorn Ranch?

Klang: Why is that?

McCarthy: He came out here and he found the skulls of two elk locked together. So they had fought, and then gotten stuck, and then they died. So T.R. named it Elkhorn Ranch after that.

For years, TR bounced back and forth between his political obligations in New York and the solitude offered here. More than silence, though, was the need to stay busy. Ranch duties couldn’t wait for a grieving caretaker. Things needed to be done, and Roosevelt threw himself into his work, sometimes spending 13 hours a day or more in the saddle.

Andes: He said, "Black care seldom sits behind the rider who moves fast enough." Something like that. Black care, I think, was depression.

The actual quote is “Black care rarely sits behind a rider whose pace is fast enough,” so Eileen nailed it.

Elkhorn had everything he needed. Distractions. Nature. Things that Roosevelt had long since learned cured whatever dark thoughts might be crossing his mind.

McCarthy: So when he wasn't ranching, or like, working in the fields, or doing his cattle rancher stuff, he would sit on the veranda, which he loved, and then he would write for up to five hours a day. And then, obviously, he was also reading a lot while he was out here. But yeah, I can definitely see why he chose this site, because if the other house was on a route that was too busy, and people were always stopping by and you really wanted some solitude, I feel like this is the place, because it's not easy to get to. And his nearest neighbors in either direction were at least 10 miles away.

And after Alice died he didn't really talk about her ever again. But I’m pretty sure he was out here when he wrote one of the only things that he wrote about her after her death. And then he just kind of closed the door on that chapter of his life, because he was not a person who liked to dwell on sad or bad things, which is something that Edith would say later.

As Baby Lee grew up in Bamie’s home, Roosevelt found comfort with the woman who would become his second wife. Her name was Edith Kermit Carow. They were married in 1886. The following year, Baby Lee joined them in Sagamore Hill. In 1889, just before the birth of their second son, Kermit, Roosevelt moved to Washington after being appointed U.S. Civil Service Commissioner. Another son, Archie, was born in 1894. It would not be the only significant personal event in Roosevelt’s life that year.

Roosevelt would go on to have four boys and one more girl. For the most part, the siblings got along well. That was a marked departure from Roosevelt’s own relationship with his brother, Elliott.

Born in 1860, Elliott was the black sheep of the Roosevelt clan, and he often tried TR’s patience. Elliott’s primary problem was the bottle. He drank heavily and often, trying to soothe the lingering pain of a serious accident. While he would sometimes attempt to curb his addiction at treatment centers, it never stuck.

All of this drove his straight-laced brother crazy, and worse than that, it threatened major scandal when Elliott got Katy Mann, his wife’s maid, pregnant in 1890.

Here’s Roosevelt family biographer William Mann, author of The Wars of the Roosevelts: The Ruthless Rise of America’s Greatest Political Family.

Mann: He was in many ways Theodore's polar opposite. Where Theodore was all about the rules of society and the expectations of society and certainly of his class, Elliott broke all of those rules. They had a lot in common as well. I mean, they grew up together. They were close as boys. They both were great sportsmen, they both loved to hunt, they both had a love of nature, but their personalities were very, very different.

Roosevelt thought Elliott was a burden not only to the Roosevelt family as a whole but to his own wife, Anna, and their three children—one of whom was future four-term first lady Eleanor Roosevelt, who later became the American spokesperson for the United Nations.

Roosevelt attempted to become his brother’s conservator to curb his reckless spending and scandalous behavior. It was an interesting role reversal. As children, it was Elliott who looked out for his older brother.

Mann: The interesting thing about their relationship when they were children is they were both at different times caretakers for each other, and I think that defines the rest of their time together, or their adult life as well. Because when Theodore was young, of course he was very famously asthmatic and very frail and fragile. The family kept him pampered and sheltered and it was expected that the younger brother would take care of the older brother. So when they were traveling, or even just around the house, Elliott looked out for Theodore, helped him along, and looked to his parents for affirmation for that. They were always, you know, grateful that Elliott took such good care of Theodore.

As Roosevelt built his body and mind, he needed Elliott less and less. Soon, he would achieve goals that were out of Elliott’s reach. Traveling in opposite directions, the brothers grew apart.

Mann: I think the first break comes when Theodore seriously says, "I want to get ahead. I want to be president of the United States." Whether he articulated that particular thought himself or if he simply said, "I want to reach for elected office," that's the moment when Elliott becomes a problem and a problem that had to be solved.

When Elliott tried putting his life together, Roosevelt did not encourage him or pat him on the back. After Elliott checked himself into a sanitarium in Europe, Anna asked Roosevelt to write Elliott a letter praising him. But TR would not do it.

To Roosevelt, his brother’s wayward behavior would only cause him harm if he managed to continue his ascendancy in politics. He believed the best way to maintain his reputation in the face of his brother’s mistakes was to make sure he could demonstrate he had tried helping Elliott. Unfortunately, his dogmatic approach may not have been in Elliott’s best interests.

Mann: It's heartbreaking when you look back because this was a man who was not drinking at the time, but they needed to institutionalize him for drunkenness. Bye sails to France and moves in to their household and essentially watches him like an eagle eye and is constantly writing back to Theodore reporting on his every move. And it's stressing the whole family out, it's stressing Elliott's wife and his children, and Elliott does, because of this, he does begin to drink a few times and they catch him. "Aha, we knew it. We knew you were going to drink too much." And eventually they do get him away from his family, they do get his wife's agreement, and he's institutionalized and it's all to be able to say, you know, should this scandal break, "Well, look, we did the right thing. We got him way from his family. He was dissolute, he was depraved. We took him away from his children because that's the right thing to do." You know, you read Eleanor Roosevelt's memoirs and it's clear she never thought that was the right thing to do because she carried a scar for the rest of her life of losing her father.

Tragedy soon found Elliott. Anna died of diphtheria in 1892. One of Elliott’s sons, Elliott Junior, succumbed to the same illness the following year. These deaths unraveled what was left of Elliott.

On August 13, 1894, TR got a telegram—by this point, a method of communication he must have grown to dread—notifying him that Elliott was in New York and in poor health. He shunned any attempts by his family to comfort him. Roosevelt honored his wishes to be left alone, and the next day, Elliott tried to kill himself by jumping out of a window. He survived, but a seizure followed. Elliott Roosevelt was dead at the age of 34.

Roosevelt had been able to compartmentalize Elliott’s problems by keeping his distance. But when he saw Elliott’s body, his coping method was of no use. He wept openly. His sister Corinne said that “Theodore was more overcome than I have ever seen him, and cried like a little child for a long time.”

Mann: We don't actually have any specific thoughts about how he felt about that, except Corinne's observation that he cried like a baby when he stood over his brother's corpse. And I just have to feel that in those tears, there was every, every emotion. There was grief, there was empathy, there was guilt, perhaps even, because the way Corinne describes it, it was a very cathartic cry. And he was a good man. Theodore Roosevelt was a good man in his heart. He wanted to do the right thing even though he was often so constrained by what was supposed to be done by, you know, society. But I have to believe that in that moment he felt all of those emotions about his brother. You know, I don't think he would ever have said to himself even, you know, "What I did was wrong," or, "I could have done something differently." I don't think he could ever bring himself to think of that.

Elliott, Roosevelt wrote, was “like a stricken, hunted creature” who had been pursued by “terrible demons.” Any thoughts of Elliott as a stain on his reputation seemed to evaporate. In death, Roosevelt saw him only as a lost soul. Though he was later exhumed and laid to rest next to Anna in the Hall family mausoleum at St. Paul’s Church in Tivoli, New York, Roosevelt initially insisted Elliott be buried in Brooklyn’s Green-Wood Cemetery, the site of the Roosevelt family plot, where he remained for two years. There, TR wrote, Elliott could be next to those who “are associated only with his sweet innocent youth.”

The empty space left by his parents, by Alice, and by Elliott could never be filled, but by the 1910s, Roosevelt had a number of important people in his life to occupy his time and his mind. There was Edith and his six children. For a time, life was relatively quiet—as quiet as TR’s life could be, anyway.

Then came America’s entry into World War I, which TR had lobbied for. He’d wanted to create a volunteer division, but president Woodrow Wilson wouldn’t allow it. Roosevelt’s sons so revered their father that they felt compelled to take up arms in his stead. Archie Roosevelt once told a historian that, “We all knew how badly Dad wanted to go, so we went for him. He always told us to lead meant to serve.”

World War I was a conflict waged with an efficient brutality. Grenades, heavy ammunition, planes, and trenches all conspired to wound an estimated 21 million soldiers. Some came back home with devastating injuries that required the use of plaster masks to hide facial disfigurements. Others took round after round of machine-gun fire. It was this unforgiving environment that the Roosevelt boys found themselves in.

Archie and Ted sailed to France. Archie was seriously wounded in the knee and arm by shell fragments. Later, Ted would suffer a leg wound. But it was Quentin who paid the ultimate price, shot down by enemy fire.

“To feel that one has inspired a boy to conduct that has resulted in his death has a pretty serious side for a father. And at the same time I would not have cared for my boys and they would not have cared for me if our relations had not been just along that line.”

Here’s Tyler Kuliberda.

Kuliberda: He doesn't talk about it, about his feelings about it publicly. He maintains everything that he had said before the war about war and about his sons being involved in it. Quentin is, you know, killed in battle, and Roosevelt calls that riding the crest of life. He thinks it's kind of the highest achievement you can have as a person, sacrificing yourself in effort of war.

Roosevelt clung to something with Quentin’s death. It was the nobility of sacrifice, a life exchanged for the greater good. Writing to King George V in response to his and the Queen’s condolences, TR said that his sons had “sailed from our shores over a year ago; their mother and I knew their temper and quality; and we did not expect to see all of them come back.”

But he could also waver. Writing to Kermit’s wife, Belle Willard Roosevelt, he lamented the pain felt by Quentin’s fiancée, Flora.

“It is no use pretending that Quentin’s death is not very terrible … It is useless for me to pretend that it is not very bitter to see that good, gallant, tender-hearted boy, leave life at its crest, when it held Flora, and such happiness, and certainly an honorable and perhaps a distinguished career.”

Kuliberda: Edith has a nice quote about the boys and their service in war. She says that you cannot raise boys to be eagles and then expect them to act like sparrows. So, losing Quentin for Roosevelt, I imagine that there was a lot of questioning of his attitude towards war, about whether or not he pressed his sons into service, and if that was a correct thing to do for all of them. We only know that he continued to say that Quentin was a valiant soldier, and that it was a higher purpose that he sacrificed himself for.

Quentin’s grave in France became a shrine that was visited by many soldiers. The Americans replaced a German cross marking the grave, and the French built a fence around it. The Roosevelts decided to leave his body there, where he had fallen in battle and where respect was being paid.

Roosevelt spent time with Edith in Dark Harbor, Maine, rowing out onto the lake to commune with nature. It was his most enduring coping mechanism. But he was older now, a man of almost 60, and the strain and toil of losing a loved one wore on his constitution. He died in his sleep on January 6, 1919, of a pulmonary embolism.

Kuliberda: Some historians have posited that six months after Quentin dies Roosevelt himself dies, so some people have put it that he had died of a broken heart in addition to physical ailments. And perhaps there's something to that. Perhaps Roosevelt couldn't continue to go on living in a world where maybe his entire view of war, which was a big part of his outlook and his world view, maybe had changed.

Prior to his death, supporters called for Roosevelt to run for president once more. Owing to his advancing age and the loss of Quentin, the man who was previously ready to run back into battle could not fathom taking on any more responsibility. “Since Quentin’s death, the world seems to have shut down upon me,” he wrote.

Four days. Four telegrams, for five tragedies. Each loss fundamentally altered how Theodore Roosevelt looked at the world—and fundamentally altered him. It’s difficult to say if TR truly conquered tragedy. You don’t leave losses like these behind—they become a part of you. What we know is that it wounded him, sometimes froze him. But it did not overcome him.


History Vs. is hosted by me, Erin McCarthy. This episode was written by Jake Rossen and researched by me, with additional research by Michael Salgarolo. Fact checking by Austin Thompson. Field recording by Jon Mayer and Tyler Klang. Joe Weigand voiced TR in this episode.

The executive producers are Erin McCarthy, Julie Douglas, and Tyler Klang. The supervising producer is Dylan Fagan. The show is edited by Dylan Fagan and Lowell Brillante.

Special thanks to Tyler Kuliberda, Holly Frey, Eileen Andes, William Mann, and North Dakota Tourism.

To learn more about this episode, and Theodore Roosevelt, visit MentalFloss.com/HistoryVs.

History Vs. is a production of iHeartRadio and Mental Floss.

History Vs. Episode 5: Theodore Roosevelt Vs. Language


Have you ever looked at a word—like although, for example—and thought: There are just too many letters in this word? If so, congratulations: You have a little something in common with Theodore Roosevelt, author of more than 30 books and 150,000 letters.

You know who else thought there were just too many letters in English words? Philanthropist and steel magnate Andrew Carnegie.

In 1906, Carnegie created, and financially supported, the Simplified Spelling Board. According to The New York Times, Carnegie thought that English had the potential to be “the world language of the future,” and that would help lead to world peace.

But according to the Board, English was “handicapped by one thing and one only—its intricate and disordered spelling, which makes it a puzzle to the stranger within our gates and a mystery to the stranger beyond the seas.”

The Board decided to pursue a course of reform by omission: Drop letters that were unpronounced or deemed unnecessary. Teaching would be made easier, written correspondence would be faster, printing would be more efficient, not to mention cheaper. One publisher estimated that using Simplified Spelling in the publishing business would save up to $40 million—which is over a billion dollars in today’s money.

The Board’s proposed reforms were published and somehow found their way to President Theodore Roosevelt, who thought that what the board was proposing made a lot of sense.

He threw his support behind their reforms, which included chopping although from A-L-T-H-O-U-G-H to A-L-T-H-O and knocking the extra S’s and ED’s from words like missed and kissed so that they were spelled M-I-S-T and K-I-S-T, respectively. P-H-A-N-T-O-M became F-A-N-T-O-M. Cats wouldn’t P-U-R-R, they’d P-U-R. And so on.

But on August 27, 1906, when TR signed an Executive Order that made the Board’s spelling reforms required in government documents, he never could have predicted how controversial his actions would be.

Simplified Spelling wasn’t the only way TR took on language in his life—he warped the pronunciation of words to get noticed, coined iconic phrases, and used the English language as a political tool. Just how did he use language to achieve his desired ends? We’re about to find out.

From Mental Floss and iHeartRadio, this is History Vs., a podcast about how your favorite historical figures faced off against their greatest foes. I’m your host, Erin McCarthy, and this week’s episode is TR vs. Language.

By the time he became president, Theodore Roosevelt was a master of many languages: He could read in French, German, Italian, and Latin (though he called reading in Latin “dreary labor”). He also spoke French and German, although his French was, in the words of his Secretary of State John Hay, “lawless as to grammar.”

He also had a very unusual speaking style—so unusual that, according to Edmund Morris, it “has the effect of burying his remarks, like shrapnel, in the memory of the listener.” Once they hear what he’s said to them, they don’t forget it.

Arika Okrent: It seems like he did have a very distinctive way of talking since it was remarked upon by people who wrote about it, and they noticed it. So it must've been … seemed a little odd or strange.

That’s Arika Okrent, linguist and Mental Floss contributor, and the person I call whenever I have a question about language.

There are some recordings of Roosevelt speaking, but as Okrent notes, most of what we know about how he spoke is through other people writing about it. And whenever they talked about how he spoke, they also usually talked about his teeth, so we’ll continue that fine tradition here.

According to Morris, Roosevelt’s “white and even” teeth would “chop every word into neat syllables, sending them forth perfectly formed but separate, in a jerky staccatissimo that has no relation to the normal rhythms of speech.”

One of TR’s colleagues summed it up by saying, “I always think of a man biting tenpenny nails when I think of Roosevelt making a speech.”

His manner of speaking led some to believe that he’d had a speech impediment as a kid. A college classmate noted that when they deliberately riled him up, he would “sometimes lose altogether the power of articulation,” and according to a colleague in the New York State Assembly, “he would open his mouth and run out his tongue and it was hard for him to speak.” Morris notes that his diction was “syncopated … sibilants hiss out like escaping steam; plosives drive the lips apart with an audible pfft.”

Okrent: Plosive P, I imagine would be like an extreme build up. So a Ppp, a lot of air coming out, maybe some spit, very forceful. P-Powerful.

Whatever the reason for how he spoke, Roosevelt leaned into it. As a young assemblyman, he’d warp the pronunciation of the word speaker, yelling “MR. SPEE-KAR, MR. SPEE-KAR!” over and over, sometimes for 40 minutes, to get the speaker’s attention.

Okrent: “This is what everyone else in Congress sounds like,” or, “This is what everyone else in New York high society sounds like.” I guess he would be picking up on that, but he used these devices to get attention, and maybe he also bristled against the elocution training that they did back then. If you went to school, and they did this at Harvard, you had elocution lessons where they taught you how to pronounce things, and do public speaking, and the right gestures to make when you do public speaking, and the right way to breathe and hold your body. And maybe he bristled against that, or maybe thought it was too British, or I don’t know...

Interestingly, when he was out in the Dakotas in the mid-1880s, TR changed his way of speaking, too. In his book Theodore Roosevelt in the Badlands, Roger L. Di Silvestro quotes the Pioneer Press as writing that “The slow exasperating drawl and the unique accent the New Yorker feels he must use when visiting a less blessed portion of civilization have disappeared, and in their place is a nervous, energetic manner of talking with the flat accent of the West.”

Whether or not Roosevelt was a good public speaker is up for debate. In the 1940s, a grad student named William Auburn Behl put that question to those who had known him, and the reviews were … not favorable. Jeremy C. Young, author of the book The Age of Charisma, put these reviews together in a blog post.

One person called TR’s gesticulations and his high-pitched voice “terrible,” while another said he “wasn’t a great speaker but one felt the force and magnetism of his personality and … his great honesty and genuineness.” As one journalist noted in 1900, “Theodore Roosevelt is a marvel as a campaigner, more from his tremendous strength, energy, force, and endurance than from finish and grace of delivery or diction.”

Young notes that, in Roosevelt’s era, most public figures, like William Jennings Bryan, used an emotional style of speaking called “personal magnetism.” But this was precisely the opposite of what Roosevelt learned at Harvard from his rhetoric teacher, Adams Sherman Hill, who said that “our feelings ought to be regulated by the facts which excite them.”

Young says that Roosevelt’s speeches “were often dry, equivocal, and monotonous,” because he’d revise them over and over and then read the typed speeches rather than speaking off the cuff, as Bryan did.

But make no mistake: Even if his speeches could be dull, TR definitely had a way with words. He coined terms and phrases that we still use today, like “bully pulpit,” “nailing jelly to a wall”—he actually said “They might just as well ask me why I do not nail currant jelly to the wall”—and the political usage of “my hat is in the ring.”

Supposedly he’s the one who called Maxwell House coffee “good to the last drop.”

One phrase we all think of when we think of TR is “Speak softly and carry a big stick, you will go far.” He said it was a West African proverb he was fond of, but according to the Oxford Dictionary of Proverbs, there doesn’t seem to be evidence that it was actually a West African proverb.

He popularized many other words and phrases, like "strong as a bull moose," "lunatic fringe," "mollycoddle," and "pussyfooting." He also popularized the phrase “weasel words,” which originally referenced the legend that a weasel can suck the contents out of an egg while leaving the shell intact. He said he heard a friend’s brother use it in reference to another person who could, in the brother’s words, “take a word and weasel it around and suck the meat out of it like a weasel sucks the meat out of an egg, until it don't mean anything at all, no matter what it sounds like it means.”

It’s a favorite phrase of Okrent’s.

Okrent: It's a metalinguistic look at language. This person is speaking this way, and the things they're doing with their words are weaselly, or the words aren't bearing meaning in the way they should. That's interesting in a sort of the pre-Orwell way of looking at what people do with words, and how they work with words, and manipulate with words.

We’ll be right back.


TR also used language to craft devastatingly colorful insults: One supreme court justice was “an amiable old fuzzy-wuzzy with sweetbread brains,” while frequent presidential candidate and Woodrow Wilson’s Secretary of State William Jennings Bryan was “a professional yodeler, a human trombone.”

Roosevelt called novelist Henry James a “little emasculated mass of inanity” while Mississippi Congressman John Sharp Williams was a “true old-style Jeffersonian of the barbaric blatherskite variety.” A blatherskite, by the way, is someone who talks a lot without making a lot of sense. Burn.

This mastery of language may not have been evident in all of TR’s speeches, but it was definitely present in some of them. There’s a reason why his 1910 speech “Citizenship in a Republic” or, as it’s more commonly known, “The Man in the Arena,” is still quoted more than a century after it was delivered:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, and comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows the great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who know neither victory nor defeat.”

But it can’t all be eloquent speeches and dee-lightful insults and catchy phrases. In his correspondence, Roosevelt used derogatory language and slurs in regards to other races and nationalities. Thomas G. Dyer addresses TR’s use of language like this in his book Theodore Roosevelt and the Idea of Race, noting that, “While TR seemed to derive considerable pleasure from the frequent private use of racial and ethnic epithets, he rarely used the terms in public … The extent of this language and the frequency of its usage indicates the preoccupation with racial differences that Roosevelt and his contemporaries had, but it also suggests Roosevelt’s professed objectivity in matters of race should not always be taken at face value.”

Henry Cabot Lodge, TR’s mentor, sometimes scrubbed that language, along with some of TR’s insults, from their published correspondence, so Lodge must have known that its use would not have painted TR in the best light.

Roosevelt also felt, in his words, that “We have room for but one language here, and that is the English language.” He believed that immigrants loyal to America should assimilate completely and be required to learn English, and that only English should be taught in schools.

In a 1916 speech to the National Americanization Committee, Roosevelt said that immigrants should become fully Americanized by learning English. This, he said, would give them more opportunities in America, and they wouldn’t be seen “only as an industrial asset.”

“Let us say to the immigrant not that we hope he will learn English, but that he has got to learn it,” Roosevelt said. “Let the immigrant who does not learn it go back.”

This type of attitude, according to Okrent, doesn’t reflect the reality of what actually happens when immigrants come to America.

Okrent: It does look kind of scary I guess when there's a lot of immigrants coming in at once, which there was at the turn of the century, and you go to neighborhoods where everyone's speaking Italian, or you go to towns in Wisconsin, everyone's speaking German and you think, “Oh no, what is this going to do to our national identity?” But looking at one snapshot like that doesn't show the whole picture, which is from generation to generation, things change very rapidly, and it's in the direction toward English. You don't have to do much to make that happen.

The first generation, the old folks, they might never really learn English, and then their kids will be bilingual, and then their kids will be fully English speakers and even forget the original language. These days, that's even frustrating for families that their kids, their grandkids don't keep up the old language, and then they lose it. The pressures of English are so great, and kids are so adept at learning language and giving over to whatever the majority culture is that they learn it, and it seems unnecessary to mandate it or make it some sort of requirement or law.

Um, even today it’s a great thing about our country that we have access to a lot of people who speak a lot of languages, and that's useful. When we need native speakers of a language, we have them, they're citizens. And there's no reason to try to stamp that out.

Not to mention the fact that English is a frequent borrower of words from other languages.

Okrent: English is not picky about what it will let in or accept. We don't have an academy. We don't have … you know, we don’t have to vote on whether we want to let this word in or not. People just start using it, and that makes the language really robust.

In fact, one TR’s favorite words was borrowed from another language. We’re talking, of course, about bully.

Okrent: That apparently comes from a Dutch word originally meaning, like, mate or brother, my buddy, my friend. It was first this term of endearment, and then it meant sort of a ruffian, and then it was specifically the guy who protects prostitutes, and eventually to what we have today. But it didn't come from English.

And then there are languages like German, which has so many words for which there’s no English equivalent. My favorite is kummerspeck, a term for the weight you gain from emotional overeating that literally translates to grief bacon.

Okrent: Yeah, and angst, and all of that schadenfreude, all the things we totally make good use of.

McCarthy: Yeah. We’ve just got to keep letting those words come in.

Okrent: Mm Hmm.

Before we get back to Simplified Spelling— the system by which words are reduced to their most basic expression in spelling, a system that TR championed—I want to take one quick diversion.

In May 1918, TR went to Springfield, Massachusetts, on a mission: To honor those Boy Scouts of Troop 13 who had sold $1000-worth of war bonds. It was there that he—a current titan of language—had an encounter with a future titan of language.

There were 10 boys being honored that May afternoon in the town’s municipal auditorium. As Donald E. Pease writes, “Roosevelt went down the line congratulating each of the young men, repeating a laudatory statement praising each boy’s accomplishment and pinning a medal on the honoree’s chest. … Each presentation was met with thunderous applause.”

There was a problem, though. TR had only nine medals.

So when Roosevelt came upon the 10th boy on stage, and had no medal to pin to his lapel, the understandably confused former president bellowed to the scoutmaster, “What’s this little boy doing here?”

The boy’s scoutmaster didn’t stop to explain the situation, just whisked young Theodor Geisel off-stage. The incident gave the future Dr. Seuss terrible stage fright, and honestly, who can blame him?

TR wasn’t the first person to support a phonetic spelling system—Benjamin Franklin, Noah Webster, and Brigham Young had all advocated for spelling reform. Noah Webster, for example, is probably the main reason the letter U was removed from spellings of American words and the Cs were replaced with Ses, which are distinguishing features between American and British English. Then again, he also suggested we spell machine M-A-S-H-E-E-N and women W-I-M-M-E-N, so, you know, they can’t all be winners.

So when Theodore Roosevelt issued an executive order in August 1906 directing the Government Printing Office to use the board’s proposed spelling system—what he called an effort to “make our spelling a little less foolish and fantastic”—he was in pretty good company.

The Simplified Spelling board was thrilled for sure: They even released a “Roosevelt Fonetic Spelling Book”—that’s phonetic with an F—after the order.

And here’s the thing: The Simplified Spelling Board, Webster, Roosevelt—they all may have been onto something … kind of.

Okrent: You know, if you ever meet Dutch people, or German people, they speak such good English, it can't be that difficult cause people do manage it. But it does have a reputation of certain parts of it being difficult, and a big one is the spelling. You have to learn it. You can't just get a few rules of thumb and then follow that like you can with most other languages. You just have to memorize all these spellings. Your engineering mind goes, like, “We could do this over, we could make this so much better. Why not?”

Well … here’s why not: Simplified Spelling looks ridiculous.

Okrent: If you already know how to read and write, you're just … you’re never going to accept these simplified spellings. It looks so funny. It looks like … you know, like a cat wrote it or something. Our spelling is just embedded in our education, and we're used to it. And sure, you know, 4-year-olds and 5-year-olds might be able to do better with phonetic spelling, they probably would. But our educational process is the process of bringing children into what we already do. And um, it's really hard to get over just the comic look of it.

And that’s exactly what the press and critics latched onto after Roosevelt signed the executive order. The backlash was immediate.

We’re going to take a quick break.


After Roosevelt signed his executive order mandating simplified spelling in government documents, everyone freaked out.

A paper in Kentucky wrote, in barely legible spelling, “Nuthing”—N-U-T-H-I-N-G—“escapes Mr. Rucevelt”—R-U-C-E-V-E-L-T. “No subject is tu hi fr”—that’s T-U H-I F-R—“him to takle”—T-A-K-L-E—“nor tu lo”—that’s T-U L-O—“for him tu notis”—spelled T-U N-O-T-I-S. “He makes tretis”—T-R-E-T-I-S—“without the consent of the Senit,” S-E-N-I-T. “He enforces such laws as meet his approval, and fales”—F-A-L-E-S—"to se”—S-E—"those that du not soot”—do spelled D-U, suit spelled spelled S-O-O-T— “him … He now assales”—A-S-S-A-L-E-S—“the English langgwidg”—“L-A-N-G-G-W-I-D-G”— “constitutes himself as a sort of French academy, and will reform the spelling in a way tu soot”—T-U S-O-O-T—"himself.”

The reaction overseas wasn’t any better. One English paper wrote, “Here is the language of 80 million suddenly altered by a mere administrative ukase”—that’s a Russian word for arbitrary command, by the way, and it’s usually reserved to describe the actions of a czar. The paper went on to say, “Could any other ruler on earth do this thing?” while another raged, “How dare this Roosevelt fellow … dictate to us how to spell a language which was ours while America was still a savage and undiscovered country!”

Amidst the brouhaha, The New York Times said that, “Roosevelt’s spelling order has done him more harm than perhaps any other act of his since he became president.”

Okrent: It's actually harder to read a long text in simplified spelling because you have to stop and sound it out, and we don't do that when we read after, you know, first, second grade. And that makes it actually harder.

It’s no wonder TR wanted to simplify spelling. Though he supposedly had a photographic memory, he was a notoriously bad speller—in fact, his wife, Edith, joked that he supported the system because he didn’t know “how to spell anything.”

Roosevelt spun the order as an experiment, writing that if the “slight changes” to the 300 words garnered popular approval, they would “become permanent without any reference to what public officials or individual citizens may feel.” If they were not popular, he said the spellings would be dropped—spelled D-R-O-P-T—concluding, “and that it all there is about it.”

But in the end, what Roosevelt wanted didn’t really matter—no one was having his strange spellings. The Supreme Court refused to follow his order, and in December 1906, Congress voted to get rid of simplified spelling, writing—in normal spelling—that the government’s documents “should observe and adhere to the standard of orthography prescribed in generally accepted dictionaries of the English language.”

Clearly defeated, TR withdrew his executive order, writing to simplified spelling proponent Brander Matthews, “I could not by fighting have kept the new spelling in. And it was evidently worse than useless to go into an undignified contest when I was beaten … But I am mighty glad I did the thing anyhow.”

Spelling finally returned to normal.

But if you think about it, in a way, Roosevelt was ahead of his time—the proof is in your text messages, where T-H-O-U-G-H is almost certainly shortened to T-H-O.

So if you’re looking to get noticed, here’s a TR pro-tip: Play around with pitch, punch those plosives, and instead of a demure “excuse me” to get someone’s attention, a loud “ex-skwas-me!” might do. And on that note … TTYL!


History Vs. is hosted by me, Erin McCarthy.

This episode was written by me, with fact checking by Austin Thompson. Joe Weigand voiced Theodore Roosevelt in this episode.

The executive producers are Erin McCarthy, Julie Douglas, and Tyler Klang.

The supervising producer is Dylan Fagan.

The show is edited by Dylan Fagan and Lowell Brillante.

Special thanks to Arika Okrent.

To learn more about this episode, and Theodore Roosevelt, visit MentalFloss.com/HistoryVs. That’s MentalFloss.com slash H I S T O R Y V S.

History Vs. is a production of iHeartRadio and Mental Floss.

How to Baffle a Bull Moose: The Time Harry Houdini Tricked Theodore Roosevelt

Harry Houdini and Theodore Roosevelt aboard the SS Imperator.
Harry Houdini and Theodore Roosevelt aboard the SS Imperator.
Library of Congress // No Known Restrictions on Publication

When the SS Imperator set sail for New York City in June 1914, it had on board bigwigs of both politics and entertainment—namely, former president Theodore Roosevelt and acclaimed illusionist Harry Houdini. Houdini was returning from a performance tour across the UK, and Roosevelt had been busy with a tour of his own: visiting European museums, meeting ambassadors, and then attending the wedding of his son, Kermit, in Madrid. Though the two men hadn’t crossed paths before, they soon became fast friends, often exercising together in the morning (at least, whenever Houdini wasn’t seasick).

The ocean liner hadn’t booked Houdini to perform, but when an officer asked Houdini if he’d give an impromptu performance at a benefit concert on the ship, he agreed, partially at the insistence of his new companion.

Little did Roosevelt know, Houdini had spent weeks plotting an elaborate ruse especially for him.

Houdini Hatches a Plan

ss imperator in 1912
The SS Imperator circa 1913.
George Grantham Bain Collection, Library of Congress // No Known Restrictions on Publication

Earlier in June, when Houdini was picking up his tickets for the trip, the teller divulged that he wouldn’t be the only celebrity on the SS Imperator.

“Teddy Roosevelt is on the boat,” the teller whispered, “but don’t tell anyone.”

Houdini, knowing there was a good chance he’d end up hosting a spur-of-the-moment show, started scheming immediately. The story was recounted in full in a 1929 newspaper article by Harold Kellock, which allegedly used Houdini’s own words from unreleased autobiographical excerpts.

Having heard that The Telegraph would soon publish details about Roosevelt’s recent rip-roaring expedition through South America, Houdini paid his editorial friends a surprise visit.

"I jumped into a taxi and went to The Telegraph office to see what I could pick up," he said. They readily obliged his request for information, and even handed over a map of Roosevelt’s journey along the Amazon.

What followed was a combination of spectacular cunning and good old-fashioned luck.

Houdini hatched a plan to hold a séance, during which he would employ a particular slate trick common among mediums at the time. In it, a participant jots down a question on a piece of paper and slips it between two blank slates, where spirits then “write” the answer and the performer reveals it.

He prepared the slates so that one bore the map of Roosevelt’s entire trail down Brazil’s River of Doubt, along with an arrow and the words “Near the Andes.” In London, Houdini had also acquired old letters from W.T. Stead, a British editor (and spiritualist) who had perished on the RMS Titanic in 1912. Houdini forged Stead’s signature on the slate to suggest that the spirit of Stead knew all about Roosevelt’s unpublicized escapades.

Upon boarding the ship, Houdini faced only two obstacles. First, he had to finagle his way into performing a public séance with Roosevelt in attendance. Second, he would have to ensure that the question his “spirit” answered was “Where was I last Christmas?” or something very similar.

Houdini cleared the first hurdle with flying colors, saying he “found it easy to work the Colonel into a state of mind so that the suggestion of séance would come from him.” Though the master manipulator doesn’t elaborate on what exactly he said about spiritualism during their conversation—later in his career, Houdini would actually make a name for himself as an anti-spiritualist by debunking popular mediums—it sufficiently piqued Roosevelt’s interest. When the ship’s officer requested that Houdini perform, Roosevelt apparently goaded, “Go ahead, Houdini, give us a little séance.”

Just like that, Houdini had scheduled a séance that Roosevelt wouldn’t likely miss—and the illusionist wasn’t going to leave a single detail up to chance.

A Back-Up Plan (Or Two)

theodore roosevelt on the ss imperator
Roosevelt relaxes aboard the SS Imperator.
George Grantham Bain Collection, Library of Congress // No Known Restrictions on Publication

Rather than bank on the shaky possibility that Roosevelt himself would pen the perfect question, Houdini prepared to stuff the ballot, so to speak. He had copied the question "Where was I last Christmas?" onto several sheets of paper, sealed them in envelopes, and planned to make sure that only his own envelopes ended up in the hat from which he’d choose a question. (It seems like a problematic plan, considering the possibility that Roosevelt would speak up to say something like "Wait, that wasn't my question," but Houdini doesn't clarify how he hoped this would play out.)

The morning of the séance, Houdini devised yet another back-up plan. With a razor blade, he sliced open the binding of two books, slipped a sheet of carbon paper and white paper beneath each cover, and resealed them.

As long as Roosevelt used one of the books as a flat surface to write on, the carbon paper would transfer his question to the white sheet below it—meaning that even after Roosevelt had sealed his question in an envelope, Houdini could sneak a glance and alter his performance accordingly.

A Little Hocus Pocus

Theodore Roosevelt poses with a map of the roosevelt-rondon expedition
Sometime after his voyage on the SS Imperator, Roosevelt posed with a map of his expedition through the Amazon.
Library of Congress // No Known Restrictions on Publication

That night, Houdini kicked off the show with a series of card tricks, where he let Roosevelt choose the cards. “I was amazed at the way he watched every one of the misdirection moves as I manipulated the cards,” he said, according to Kellock’s article. “It was difficult to baffle him.”

Then, it was time for the séance.

"La-dies and gen-tle-men," Houdini proclaimed. "I am sure that many among you have had experiences with mediums who have been able to facilitate the answering of your personal questions by departed spirits, these answers being mysteriously produced on slates. As we all know, mediums do their work in the darkened séance room, but tonight, for the first time anywhere, I propose to conduct a spiritualistic slate test in the full glare of the light."

Houdini distributed the slips of paper, gave instructions, and then solicitously passed Roosevelt one of the books when he saw him start to use his hand as a surface. As Roosevelt began to write, composer Victor Herbert, also in attendance, offered a few shrewd words of caution.

"Turn around. Don't let him see it," Houdini heard him warn Roosevelt. "He will read the question by the movements of the top of the pencil."

"The Colonel then faced abruptly away from me and scribbled his question in such a position that I could not see him do it," Houdini said, adding, "Of course that made no difference to me."

After Roosevelt finished, Houdini took the book and slyly extracted the paper from the inside cover while returning it to the table.

In an almost unbelievable stroke of luck, Roosevelt’s question read “Where was I last Christmas?” Houdini wouldn’t need to slip one of his own envelopes between the slates after all.

"Knowing what was in the Colonel's envelope, I did not have to resort to sleight of hand, but boldly asked him to place his question between the slates himself," Houdini said. "While I pretended to show all four faces of the two slates, by manipulation I showed only three."

Then, after Roosevelt stated his question aloud to the audience, Houdini revealed the marked-up map, bearing the answer to Roosevelt’s question signed by the ghost of W.T. Stead.

In a 1926 article from The New York Times, Houdini describes Roosevelt as “dumbfounded” by the act.

“Is it really spirit writing?” he asked.

“Yes,” Houdini responded with a wink.

In Kellock’s account, however, Houdini confessed that “it was just hocus-pocus.”

Either way, it seems that Houdini never explained to Roosevelt exactly how he had duped him, and Roosevelt died in 1919, a decade before Kellock’s detailed exposition hit newsstands.

To fully appreciate the success of Houdini’s charade, you have to understand just how difficult it would’ve been to pull one over on a sharp-witted guy like Theodore Roosevelt. Dive into his life and legacy in the first season of our new podcast, History Vs. podcast, hosted by Mental Floss editor-in-chief Erin McCarthy.