The Last Days of Theodore Roosevelt

A message was sent from Paris in the summer of 1918 to American news agencies.

“Watch Sagamore Hill in event of…”

The rest of the message had been deleted by wartime censors, but Theodore Roosevelt knew what it meant.

He said, “Something has happened to one of the boys.”

(If you’d rather listen than read, check out this episode of the History’s Trainwrecks Podcast):


The Roosevelt sons — Ted Jr., Archie, Kermit, and Quentin, had all gone to the front lines of the fighting in the First World War. Ted Jr. and Archie had been assigned to General John J. Pershing’s headquarters in Paris. Kermit had been posted to Mesopotamia with the British, and Quentin was a first lieutenant in the Ninety-Fifth Aero Squadron. The night before he left home, his mother tucked him in at bedtime.

They saw him off the next morning. Teddy’s daughter Alice said, after her parents had left, “The old Lion perisheth for lack of prey and the stout Lion’s whelps are scattered abroad.”

Sagamore Hill was empty now, except for Edith — who was daily trying to contain her worry over her sons — and Flora Whitney, Quentin’s fiancée.

Ted Jr. and Archie had been posted to an infantry regiment that would be one of the first American units sent into combat. When he heard the news, Teddy was painfully reminded of the snub he had received at the hands of Woodrow Wilson, who had forbidden him to raise a regiment with himself in command to go fight in France.

So did the news that William Howard Taft had been appointed a major general. The title was only a “certificate of identity,” since he was an officer in the Red Cross. “Major General Taft!” Teddy joked bitterly. “How the Kaiser must have trembled when he heard the news!”

Teddy was full of complaints, trying to live vicariously through his boys. He was incensed at the news that Ted Jr. and Archie would be serving in the same unit, which he would never have permitted if he was in command, and at Kermit’s attempt to get a staff job with the British Army so his wife could join him. “This is war,” Teddy wrote. “No officer must try to get his wife near him on the campaign. He must devote himself solely to his grim work.”

Quentin wrote sporadically. He was prone to depression himself, which was exacerbated by visits to his older brothers, who chided him about not getting into combat. His father was no help, writing “You and your brothers are playing your parts in the greatest of the world’s great days, and what man of spirit does not envy you?”

It seemed pretty clear who the envious “man of spirit” was.


The end of the war was in sight, and Woodrow Wilson was carefully planning his grand entrance on to the world stage. He sent his Fourteen Points to Congress, which outlined his vision for the postwar world. French Prime Minister Clemenceau, who had asked Wilson to send Teddy to Europe the year before, was unimpressed with the Fourteen Points. “The good Lord only had ten,” he said.

But with Allied victory seeming clear, and with American boots at long last on the ground, the American President was about to become a powerful world figure, a role he was going to end up in far more than one he had brought about.

Former President William Howard Taft said, “I am sorry from the bottom of my heart for Colonel Roosevelt. Here he is, the one man in the country most capable of doing things, of handling the big things in Washington, denied the opportunity…my heart goes out to him.”

But Teddy’s political problems were the least of his worries.


His health grew worse. His malarial attacks increased with the tremendous stress he was under, fearing that the day would come when he would have to tell his wife that one of her sons was dead. He suffered from an abscess, and after being examined by his doctors he was immediately sent to Roosevelt Hospital in New York (named for one of his philanthropic cousins) where his fever climbed and he went into surgery. The next day he suffered from acute dizziness. Reporters in the hotel lobby began a deathwatch. At nine in the morning on February 8, 1918, a rumor started that he had died.

He recovered slowly, now deaf in one ear from abscesses in his aural canal. One of the first letters he returned was from Quentin, who had been posted to flight instructor school to train incoming pilots. Teddy pressed his son to keep trying to get a combat assignment. Quentin wrote his aunt that he had had pneumonia and had been sent to the Riviera to recuperate. His brother Archie “accused him of ‘slacking’ behind the lines.” Quentin dutifully requested to fly combat missions, which was approved.

Ted Jr. had been temporarily blinded by a gas attack at the front. Archie was gravely wounded by shrapnel. Kermit had been cited for meritorious service in North Africa. Quentin shot down his first enemy plane. A friend told Teddy, “Colonel, one of these days those boys of yours are going to put the name of Roosevelt on the map.”


“It seems dreadful that I, sitting at home in ease and safety, should try to get the men I love dearest into the zone of fearful danger and hardship,” Teddy wrote Kermit.

Dreadful indeed. A cable arrived from General Pershing: “Regret very much that your son Lt. Quentin Roosevelt reported as missing…Will advise you immediately on receipt of further information.”

Edith Roosevelt’s diary entry for that day was, unusually, left blank.

Before breakfast the next day, reports from overseas confirmed that Quentin had been killed. German soldiers had photographed him lying on the ground next to his shattered plane.

“But — Mrs. Roosevelt?” Teddy asked the reporter who had brought the news. “How am I going to break it to her?”

He went into the house and came out half an hour later with a statement.

“Quentin’s mother and I are very glad that he got to the Front and had a chance to render some service to his country, and to show the stuff there was in him before his fate befell him.”

Teddy kept his engagements that day as condolence telegrams poured in, refusing to cancel any of his plans, no doubt hoping to be distracted from his grief. He had lunch at the Harvard Club with Albert Shaw, editor of the American Review of Reviews, who said, “It may not be true. I would not make up my mind until I hear from General Pershing direct.”

“No,” Teddy told him. “It is true. Quentin is dead.”

After he left, one of the other men at the table noted, “The old side of him is gone, the old exuberance, the boy in him has died.”


There was an effort underway to draft him for governor of New York. His old friends Elihu Root, William Howard Taft, and even Charles Evans Hughes were all firmly back on his side and pushing for it.

“I have only one fight left in me,” Teddy told them. “And I think I should reserve my strength in case I am needed in 1920.”

He and Edith left Sagamore Hill for Maine, to escape the house that still bore so much of Quentin’s presence. Teddy spent a lot of time in a boat alone, in the middle of the bay. Teddy’s biographer Edmund Morris wrote, “What made this loss so devastating to him was the truth it conveyed: that death in battle was no more glamorous than death in an abattoir. Under some much-trodden turf in France, Quentin lay as cold as a steer fallen off a hook.”

The army offered to return Quentin’s body for burial in the U.S. Teddy wrote back, “We greatly prefer that Quentin shall continue to lie on the spot where he fell in battle.”

Once back at Sagamore Hill, Teddy was seen in the stable, “his face buried in the mane of his son’s pony, sobbing “Poor Quentyquee!”


Woodrow Wilson was on top of the world. The warring factions had asked him to negotiate the peace, based on the outline of his Fourteen Points. Teddy sent a telegram to Henry Cabot Lodge hoping for the negotiations to stop. He knew Wilson better than most, and was not won over by pedantic ideals. As ever, he could foresee the end result of a Wilson-led peace — another war. “Let us dictate peace by the hammering of guns,” he wrote, “and not chat about peace to the accompaniment of the clicking of typewriters.”

Wilson asked the voters in the 1918 midterm elections to retain a Democratic House and Senate. “If you have approved of my leadership and wish me to continue to be your unembarrassed spokesman in affairs at home and abroad, I earnestly beg that you express yourselves unmistakably to that effect by returning a Democratic majority to both the Senate and the House of Representatives.”

The Republicans took both houses of Congress, foreshadowing victory in the presidential election of 1920.

If only Teddy could do it.


He was suffering from a list of ailments, adding rheumatism to his chronic hypertension and malaria attacks.

He was back in the hospital when the armistice was signed on November 11, 1918, and could hear the roaring of crowds and loud music from Columbus Circle outside his window.

Even flat on his back in a hospital bed, political strategists acknowledged that he could get the 1920 Republican nomination if he wanted it. Teddy said, “Well, probably I shall have to get in this thing.”

His hat was, for the last time, in the ring.


He turned sixty while in the hospital, but was back home at Sagamore Hill byChristmas. He noticed that his little grandson, Richard Derby, had asthma, “like himself as a child.”

Instead of the bedroom he and Edith shared, he had himself installed in the one next to it, with a sunny exposure to keep him warm in the winter while he recovered.

He read the daily papers, watching from afar Woodrow Wilson’s triumphant tour through Europe, knowing that the Fourteen Points, and lasting peace, was a pipe dream. He got himself ready for 1920, believing once again that he was the right man for this moment.

Edith wrote Ted, Jr, “I think he had made up his mind he would have to suffer for some time and with his high courage had adjusted himself to bear it.” Teddy had overcome the limitations of his body before. As the new year of 1919 dawned, he believed he could do it again.

Edith remembered his “exceptionally gentle mood, and whenever she passed the sofa she could not help kissing him and stroking his short, little-boy’s hair.” At ten p.m., he asked her to help him sit up. “He said he felt as if his lungs or heart were about to give in.” She sent for the doctor, who examined him and found nothing amiss.

He went to bed at midnight, and Edith checked on him at two a.m. She woke up at four “to find the nurse standing over her.” She rushed into the next room, calling his name.

There was no answer.


“Death had to take Roosevelt sleeping,” Vice President Thomas Marshall said, “for if he had been awake there would have been a fight.”

Senator Henry Cabot Lodge addressed a joint session of Congress where he eulogized his old friend. “So he passed over,” Lodge quoted John Bunyan, “and all the trumpets sounded for him on the other side.”

Teddy Roosevelt was laid to rest at the top of a hill at Youngs Cemetery in Oyster Bay. He had picked the spot because he liked the birdsongs he heard there. It also afforded a grand view of the bay.

The coffin was lowered into the ground, the sun twinkling off the silver plate on it that read:


October 27, 1858 — January 6, 1919

After most of the mourners had made their way down the hill, one lone figure stayed behind at the graveside. William Howard Taft stood there “for a long time, crying.”


We never like to play “what-if” with history here, but it seems like the best alternative to what happened in 1908 would have been for Teddy to run again in a presidential election he would easily have won. He could then have appointed William Howard Taft to his coveted seat on the Supreme Court, had one final earth-shaking term as President, and retired to Sagamore Hill as a venerated elder statesman, his work finally done.

America was moving on, into the self-centered, isolationist, money-grubbing, lavish-spending 1920’s. It was not an America that had a high place for a man like Theodore Roosevelt. Businessman presidents were going to take over for a few years, and, while they kept their eyes on the bottom line, the world would catch fire.

The man who came along to put the fire out had learned a lot from his fifth cousin. So did his wife, Teddy’s niece. The powerful political marriage of Franklin and Eleanor Roosevelt would bring the world back from its deadly spin, and set the tone for the rest of the century. The memory of TR — and what he stood for — would never truly disappear from the land. A small boy in an Oyster Bay schoolhouse tasked to describe Teddy for a homework project called him “a fulfiller of good intentions.”

A paragraph by Theodore Roosevelt’s biographer Edmund Morris presents as good a summary of Teddy as we’re likely to get:

“He left behind a folk consensus that he had been the most powerfully positive American leader since Abraham Lincoln. He had spent much of his two terms (and subsequent campaigns) crossing and recrossing the country, east and west, north and south, reminding anyone who would listen to him that he embodied all America’s variety and the whole of its unity, that what he had made of his own life was possible to all, even to boys born as sickly as himself. Uncounted men, women, and children who had crowded around the presidential caboose to stare and listen to him now carried, forever etched in memory, the image of his receding grin and wave.”

Many of those Americans were still around when the train came back to their towns, now ravaged by the Great Depression. They once again saw a famous grin and heard an optimistic voice telling them they were capable of anything, even saving the world.

It was another Roosevelt, bringing hope back to the United States of America.

Teddy would have been proud.




There are many historical figures who seemed to have everything going for them — Aaron Burr, George McClellan, Herbert Hoover, Douglas MacArthur, and more — but lost out to people who had been relative nobodies. History’s Trainwrecks tries to figure out what happened…

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Host of the History’s Trainwrecks Podcast — this is the stuff they never taught us in history class.

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