Major General Theodore Roosevelt?

There was no way Woodrow Wilson was going to let former President Theodore Roosevelt anywhere near Europe during the First World War.

The Republicans had nominated Justice Charles Evans Hughes to carry their torch in the 1916 presidential election. Hughes was a lukewarm choice, derived from a wide open contest in which many of the power brokers in the party wanted the nomination for themselves. Even though the country and the world were facing colossal threats, the GOP turned away from their own colossus to select a candidate that nobody really wanted.

Teddy was deeply hurt by this shunning by the Republicans, and when asked to comment on the news that the president had sent the National Guard to the Mexican border replied, “Let Hughes talk — it’s his fight.”

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

But always a good Republican, and a fervent enemy of Woodrow Wilson, Teddy allowed himself to be drawn into the campaign. He kept his public events to a minimum, knowing that his own forthright style would draw attention to Hughes’ weakness. He privately called Hughes “the Bearded Lady.”

Woodrow Wilson was riding high. The economy was running at full-speed, profiting enormously from the war. The president had returned to his progressive agenda by taking the side of labor in a railroad strike that he successfully settled. Compared to grumpy and sickly Theodore Roosevelt, Wilson looked young and strong, even though he was older.

A clever and wily politician, Wilson campaigned against Teddy, even though Hughes was his opponent. In a stump speech he claimed that there was only one voice in the GOP, “a voice for war not peace, shot through with every form of bitterness, every ugly form of hate, every debased purpose of revenge…discontented and insurgent.”

For every American who was going to vote for Hughes in hopes of getting Teddy back, at least a little, Wilson had pretty much nailed Teddy’s current mood as decidedly unoptimistic and out of step with the path the country was already on — one of prosperity and a mature outlook.

Teddy campaigned right back, taking aim at Wilson’s famous slogan: “He kept us out of war.” He said, “President Wilson’s ignoble shirking of responsibility has been clothed in an utterly misleading phrase, the phrase of a coward, He kept us out of war. In actual reality, war has been creeping nearer and nearer, until it stares at us from just beyond our three-mile limit, and we face it without policy, plan, purpose or preparation.”

He wasn’t wrong. He also wasn’t running for President, so his words were lost.

But it was military matters, more than politics, that had Teddy’s attention in 1916.

He wanted to go to war.


He sent a letter to the Secretary of War in July, requesting permission to raise a division of volunteers. He had planned a vacation to Jamaica, but told the Secretary he would hold off if needed:

“In view of breaking relations with Germany I shall of course not go to Jamaica, and will hold myself in readiness for any message from you as to the division. I and my four sons will of course go if volunteers are called for…”

War Secretary Newton Baker wrote back, “No situation has arisen which would justify my suggesting a postponement of the trip you propose.” This was the first in a string of communications intended to subtly dissuade Teddy from going off to fight. The Wilson Administration had embarked on another step in the so-called “Wilson Tango,” adopting a strategy called “armed neutrality.”

Foreign Policy Safety Tip Number Two Hundred Fifty Seven: If everyone knows you don’t want to go to war, there’s no point in trying to be tough.

Once more events took matters out of Wilson’s hands as news of the Zimmerman telegram flashed across the country. Germany had sent a communique to its minister in Mexico, proposing a scheme whereby Mexican forces would invade the U.S. and take back Texas, New Mexico, and Arizona. It was suggested that Japan would join in and attack the West Coast by sea.

Theodore Roosevelt was pretty peeved. He had foreseen both possibilities as early as 1910, when he had warned President Taft about “a war in which Mexico was backed by Japan or some other big powers.” He had predicted in 1914 that if Germany defeated Britain it would form “an alliance with Japan against the United States.”

Well. That sounds familiar. Teddy may have been a bitter old grump at this point, but his ability to predict world events was still spot on.

He sent a message to Secretary Baker in the wake of the Zimmerman telegram: “I again earnestly ask permission to be allowed to raise a division for immediate service at the front.”

Poor Secretary Baker, caught between Wilson and Roosevelt, wrote back that no forces would be raised without an act of Congress, and that general officers for volunteer divisions would come from the regular army.

Teddy asked his old friends — and sometime enemies — Elihu Root and the recently defeated Charles Evans Hughes to “persuade the President to let him fight in Europe.”

“I shall not come back,” Teddy told them. “My boys may not come back, my grandchildren may be left alone, but they will carry forward the family name. I must go.”

He found himself in Washington shortly after Wilson’s speech to Congress asking for a war declaration against Germany. He went to the White House to see Wilson, to ask in person for permission to raise a division, but the president was unavailable, likely on purpose. He knew what Teddy wanted.

“I am sorry to not have seen the President,” he told a reporter on his way back to New York.


The four Roosevelt sons, knowing what was expected of them, assembled at Sagamore Hill with their father to plan out their involvement in the war. “None would sit behind a steel desk.” Only frontline combat was considered, while their mother hovered, brooding. Her youngest son Quentin had a bad back and worse eyesight, so she tried to dissuade him, but he was determined to go.

Ted Jr. and Archie were sure of officer commissions in the infantry. Kermit was more difficult to place, as he had always been, so there was talk of him going to the front in North Africa. Quentin wanted to be a fighter pilot.

Teddy went back to the White House on April 9th without calling ahead. “I’ll take chances on his trying to snub me.” He managed a meeting with Wilson, later telling reporters that he had asked permission to raise a division to go fight in France and that the President “had neither accepted nor rejected his request.”

Teddy was optimistic on the surface, but knew full well who he was dealing with. With a cagey operator like Wilson, no answer was the same as saying no. He admitted that the President “seemed to take it well, but — remember, I was talking to Mr. Wilson.”

He tried going to Congress, sending a letter to the chairman of the Foreign Affairs Committee, proposing that his expeditionary force be sent “to put our flag on the firing line.” In short, he didn’t think America should wait for full mobilization before sending a force to Europe. “Let us pay with our bodies for our soul’s desire.”

This fit Teddy’s usual post-election pattern. In 1908 and 1912, after not being elected President, he left the country to go do things that stood a good chance of getting him killed. The same was true after the election of 1916. Whenever he wasn’t returned to office, Teddy’s first impulse was to put himself in harm’s way. He expected his service at the front to be a suicide mission.

Secretary Baker and President Wilson must have suspected this, but they had other concerns too. Baker sent Teddy a letter on April 15 telling him his request was once again denied. “This policy,” Baker said, “does not take to underestimate what, if any, sentimental value would attach to a representation of the United States in France by a former President of the United States.” He added that general officers would be chosen from the ranks of men “who have devoted their lives exclusively to the study and pursuit of military matters, and have made a professional study of the recent changes in the art of war.”

Baker had found two ways to call Teddy a has-been in the same letter: his military experience was astoundingly out-of-date, and he was only a former President. The intent (and one might see the crafty hand of Woodrow Wilson here) might have been to send Teddy into a depressive funk that would sideline him from the international stage.

Which worked. Teddy’s recent string of setbacks already had him at a low point, and whenever he was in this kind of mood, he lost his ability to see the entire chessboard, so to speak. Woodrow Wilson, unaffected by emotion, saw things very clearly.

European representatives, on behalf of their leaders, had been quietly asking for Theodore Roosevelt to come to Europe. Marshall Joffre of France had requested the Roosevelt division be attached to his troops, knowing the huge morale boost Teddy would bring to the soldiers stuck in trenches at the front. A British mission had come to Washington as well, led by admirers of the former President. Arthur Balfour, head of the British delegation, quietly went to Sagamore Hill for tea with Teddy. “The State Department, alerted by a sudden deployment of Secret Service agents, was powerless to stop him.”

Georges Clemenceau published a letter he had sent to President Wilson, asking him to let Teddy come to war, with a little dig at Wilson’s professorial bent: “It is possible that your own mind, enclosed in its austere legal frontiers…has failed to be impressed by the vital hold which personalities like Roosevelt have on popular imagination,” the letter said, making clear which president Clemenceau preferred. “The name Roosevelt has legendary force in our country at this time. Send them Roosevelt. I tell you because I know it — it will gladden their hearts.”

Wilson had to know (and Teddy should have as well), that if Theodore Roosevelt set foot on European soil, he would at once command the world stage. He was immensely popular in Europe, widely regarded as an expert on international affairs and, as his Nobel Prize attested, a certified peacemaker. The Germans had already started sending some initial peace overtures by this point. The war was deadlocked. Hundreds of thousands of men were dying pointlessly as the stalemate dragged on. Teddy Roosevelt showing up would be all the provocation needed to get the belligerents to the table to talk peace.

Wilson knew that even if Teddy was sent at the head of an inexperienced volunteer division, he would never get anywhere near the front. He would be immediately drafted by desperate France and England into chairing a peace conference, which his international stature could actually bring to a successful conclusion.

In short, Teddy would steal Woodrow’s thunder.

If Teddy’s mind and emotions had been in a better place, he would have seen this himself. Instead of a suicide mission to the Western Front, he could have abandoned his dreams of military glory and got on a ship to London, where he just might have ended the war, achieved international acclaim, and paved a straight path back to the White House in 1920.

But in his current state, the college professor in the White House was able to play Teddy like a fiddle. Congress, at the urging of Teddy’s supporters, passed a conscription bill with a rider attached allowing the president to approve a division of volunteers with Teddy as its commander. Which Wilson declined to do. “It would be very agreeable for me to pay Mr. Roosevelt this compliment, and the Allies the compliment, of sending to their aid one of our most distinguished public men, an ex-President who has rendered many conspicuous public services and proved his gallantry in many striking ways,” Wilson wrote. “But this is not the time…for any action not calculated to contribute to the immediate success of the war. The business now at hand is undramatic, practical, and of scientific definiteness and precision.”

It was classic Wilson. An initial empty compliment, followed by the killing blow. In his view, Teddy was an empty showman — dramatic, impractical, and imprecise. He would add nothing to the military advancement of the war. Wilson knew the right buttons to push. By invalidating any military contributions Teddy might make — which was all Teddy cared about at that moment — Wilson deftly headed off any chance of Teddy taking the war — and the peace — out of his hands.

Teddy, still focused on his suicide mission, complained to Elihu Root: “I told Wilson that I would die on the field of battle, that I would never return if only he would let me go!”

“If you could really convince the President of that,” Root replied. “I’m quite sure he would send you at once.”

But Root knew better. Wilson didn’t need Teddy to die in battle to get him out of the way. Better to leave him useless and lost at home. Wilson was planning triumphant diplomacy, and like the two close presidential elections he had won, the only man standing in his way was Theodore Roosevelt.

But all Teddy wanted was to fight, and if he couldn’t, he wanted to make sure his sons did. He prevailed upon his stature, and the sympathy he gained from having his hopes of leading a division smashed, to get his sons assigned to the first fighting units going overseas. He petitioned General Pershing, whom he had promoted when he was President, to assign Ted Jr. and Archie to his staff and eventual field commands.

He was able to get his other sons, Kermit and Quentin, on their way to the war as well. “I don’t care a continental whether they fight in Yankee uniforms or British uniforms or in their undershirts, so long as they’re fighting.”

Teddy had transferred his death wish to his sons, who knew their father would accept nothing less than front line combat roles for them.

His youngest son Quentin said. “Well, you know it’s rather up to us to practice what father preaches.”




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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