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Theodore Roosevelt and Woodrow Wilson: A Bitter Rivalry

By Michael F. Bishop

One of the bitterest presidential rivalries in American history was between two men who had much in common: Theodore Roosevelt (1901-1909) and Woodrow Wilson (1913-1921).

Both were Progressives who had an expansive vision of the role of government in modern life. Each disdained the work of the founders (Roosevelt had a particular loathing of Thomas Jefferson), viewing the Constitution as an outmoded charter that prevented the activist government they favored. And both were prolific writers and authors of influential historical works.

Furthermore, John Milton Cooper, Jr., in The Warrior and the Priest: Woodrow Wilson and Theodore Roosevelt, observed that they “seized upon and expanded three powerful aspects of the office—public dramatization, education of the people, and party leadership.”

But their differences were profound, and would lead to a bitter clash in the years leading up to World War I. Wilson was a cloistered academic who became President of Princeton, and later was persuaded by the New Jersey Democratic machine to run for governor in 1910. Roosevelt was an aristocratic New Yorker who scandalized his family and social set by plunging into politics at a young age. While Wilson wrote his books and taught his classes, Roosevelt’s scholarly work was combined with rustling cattle in the Dakota Badlands and fighting the Spanish in Cuba. Wilson celebrated cerebral pursuits; Roosevelt championed what he called “the strenuous life”.

Ironically, given his disdain for Wilson, it was Roosevelt’s decision to mount a White House comeback in the form of a third-party bid for president in 1912 that assured his rival’s victory. Despite running in the general election on the Progressive ticket, he split the Republican vote and cost his handpicked successor, William Howard Taft, a second term. (This caused Taft little heartbreak; he never enjoyed the presidency, and later would achieve his fondest goal: appointment to Chief Justice of the Supreme Court.)

When war began in Europe in the summer of 1914, Wilson pledged the United States to neutrality and offered to mediate between the two sides. Roosevelt scorned this restraint and argued passionately that America should join the war on the side of the Allies. In 1915 he wrote to his son, Kermit, “It is just as it was a century ago when Jefferson, another shifty phrasemaker who was ‘too proud to fight,’ was president. Jefferson dragged our honor in the dust and was responsible for the ignoble conduct of the war that followed; but he pandered to the worst side of the people, and they supported him with enthusiasm.” He made such attacks publicly during the 1916 election, while campaigning for Wilson’s opponent.

Wilson was stung; “The president doesn’t like Theodore Roosevelt,” observed one of his aides. But still lusting for battle, Roosevelt swallowed his pride and asked Wilson for an army commission during a White House visit. The ex-president later recounted, “I told Wilson that I would die on the field of battle, that I would never return if only he would let me go!”

But Wilson would have none of it, coldly observing, “I really think the best way to treat Mr. Roosevelt is to take no notice of him. That breaks his heart and is the best punishment that can be administered.”

For all his titanic energy and the enormity of his ambitions, Roosevelt’s nearly two terms as president were notable for their relative peace and stability. It was Wilson who took his country into a world war, something about which the martial Roosevelt could only dream. This only added to his bitterness.

Neither enjoyed long retirements. Roosevelt had entered the White House at the age of forty-two, still the youngest president in American history. But he never fully recovered from a near-fatal post-presidential expedition to the Amazon, and the heartbreak of losing his beloved son, Quentin, in the war for which yearned, broke his heart. He died in 1919, at sixty. In his last year of office, Wilson stormed the country with messianic zeal in support of the League of Nations; the effort broke his health and led to a stroke that left him temporarily incapacitated (and his wife running the country). He died less than three years after leaving the White House.

For all the intensity of their rivalry, Roosevelt and Wilson increased the power of the federal government and expanded the reach of the presidency, with consequences that would forever transform the United States.


Michael F. Bishop is the former executive director of the International Churchill Society and the Abraham Lincoln Bicentennial Commission.