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September 10, 2025

It Would Take a Big Man to Fill Roosevelt’s Shoes

Teddy Roosevelt pointed to William Howard Taft as his successor, but wrongly assumed Taft would simply follow the former president’s path and take his advice.

William Howard Taft was a scholar, graduating second in his class at Yale and excelling in law school while simultaneously working as a “courtroom” reporter. Most students of presidential politics are surprised to learn that he was also an accomplished athlete who chose to concentrate on his love of books and learning instead of the playing field.

Born into a large Unitarian family in Ohio headed by an attorney father who had served first as Secretary of War and then as Attorney General in President Ulysses S. Grant’s administration, while later being posted to the Austrian-Hungarian Empire as U.S. Minister in Chester A. Arthur’s presidency, his childhood as the son of a national political figure was equally balanced by a strong mother. She advocated for women’s rights, kindergarten for all children, and the importance of the arts, while encouraging intellectual curiosity in her children. His scholarly bent seemed the natural result of his family environment and access to all facets of knowledge.

His career followed a somewhat predictable path, too. From assistant prosecutor in Hamilton County, Ohio, to Ohio Superior Court judge to U.S. Solicitor General by age 33, and then a seat on the Sixth U.S. Circuit Court of Appeals, Taft’s not-so-secret dream was a future appointment to the U.S. Supreme Court. In his role as Solicitor General, he became friends with Civil Service Commissioner Theodore Roosevelt, a connection that would play prominently in his future.

Immediately following the Spanish-American War, President William McKinley appointed Taft to establish a new civilian government in the U.S. protectorate Philippine Islands. Not particularly thrilled to enter what was a political whirlwind, he arrived on assignment amidst a ferocious fight involving 70,000 U.S. military troops and a rebel force led by Emilio Aguinaldo. Taft frequently clashed with his military counterpart, General Arthur MacArthur, and once the rebellion had been quelled, the civilian governor was successful in MacArthur’s removal.

Taft then focused on his love of the law, crafting a constitution for the Philippines based on the U.S. Constitution and its Bill of Rights, minus the right to trial by jury. While he created a civilian government with his own role as civil governor, he worked diligently to create a strong judicial system, public schools, and healthcare facilities, as well as to facilitate the purchase of former Catholic lands for distribution to the peasants with low-cost loans for home construction. He was so focused on completing the governmental plans that he turned down two Roosevelt appointments to the U.S. Supreme Court, possibly also because his beloved and politically astute wife, Helen, felt the High Court was a dead end to real power and visibility. She often whispered the words “White House.”

When Roosevelt returned later with a Secretary of War offer, Taft agreed, knowing he could continue his work in the Philippines. Charged with oversight of the Panama Canal and functioning as quasi-governor of Cuba, Taft traveled the world as the president’s emissary and official spokesman. The bond between the two men grew, although their personal styles differed.

Roosevelt promised not to seek reelection in 1908 and pointed to Taft as his successor, assuming he would simply follow Roosevelt’s presidential path and take advice frequently from the former president. Imagine Roosevelt’s surprise when Taft was chosen as the Republican nominee from a vast field (with Roosevelt’s endorsement) and then garnered 51.6% of the popular vote against William Jennings Bryan in the general election (with Roosevelt’s endorsement), but then the new president decided to seek his own counsel. Roosevelt saw Taft’s presidency as a challenge to his own legacy, and after the new president dismissed Gifford Pinchot and targeted U.S. Steel, one of Roosevelt’s “good corporations,” the former president was outraged and outspoken.

Taft leaned heavily on the most conservative wing of the Republican Party, which had often seen Roosevelt as too liberal and too controversial. Taft’s wife, too, dismissed Roosevelt as a radical and “rough” man, and he valued her opinion, since he was often not particularly political. Taft distanced himself from Roosevelt, and by the final year of his administration, Roosevelt was attacking his former friend in the press. The 1912 election would play out like a Greek drama or a modern-day soap opera.

Let’s return next week to examine Taft’s domestic and foreign policy actions. Then, you can decide “thumbs up” or “thumbs down” on his presidential legacy.

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