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July 23, 2025

The Hero of San Juan Hill Charges Into the White House

No one would ever accuse Theodore Roosevelt of being powerless in his quest for his nation. In fact, he is often considered the first strong president of the modern era.

Teddy Roosevelt has intrigued presidential historians since his arrival — dignified but thunderous — on the national political scene. Something about the man’s humanity seemed to strike a chord with even those who were not normally interested in the alternating excitement and dullness that accompany presidential actions, speeches, and interactions with both Congress and the state leadership cadre in a federal system. Theodore Roosevelt seemed to be a tonic of energy applied to a national malaise after a period of presidents, often skilled but somewhat lackluster, who had been labeled the “Powerless Presidents of the Gilded Age.”

No one would ever accuse President Roosevelt of being powerless in his quest for his nation. In fact, he is often considered the first strong president of the modern era.

Who was this youngest man ever to step into the presidential role? (John F. Kennedy was the youngest elected president, but Roosevelt holds the distinction of being the youngest at the time of oath, obviously by virtue of William McKinley’s assassination.)

If I mention his name in a conversation, I imagine that a multitude of images flash through thoughts. Sickly child-turned-outdoors enthusiastic. Public servant. Tragic personal life but strength in moving forward. Former governor of New York. Author. Assistant secretary of the Navy. Energetic candidate. “Big stick” foreign policy leader. Unable to walk away after walking away…

All are true, and all contribute to the complexity of the man and the president.

Born just prior to the U.S. Civil War to a comfortable family, Theodore Sr. and Martha “Mittie” Bulloch Roosevelt, Teddy actually grew up in Georgia before becoming a lifelong adult New Yorker. The sickly child with bad eyesight overcame his asthma and its accompanying physical weakness by willpower coupled with a rigorous regime of exercise and exertion. After entering Harvard at age 18 and pursuing a wide range of studies — in some ways like Thomas Jefferson, he loved knowledge — he enrolled at Columbia Law, only to decide that the law was too tedious and deskbound for him. Instead, public service appealed, and once he stepped into the arena, he would remain a public person for a lifetime.

The tragic death of his wife and mother within hours of each other threatened to shatter the young man, but, once again, the outdoors saved him and fueled a personal love that would lead to a gathering of national treasures: our National Park System. (Pause for thunderous applause.) He would ranch, hunt, and explore the natural wonders of the Dakotas until he had healed well enough to return to his work goals in the public sector. He would remarry and, along with first daughter Alice, he and his second wife, Edith Kermit Carow, would raise a boisterous household of four talented and strong-willed sons, Theodore, Kermit, Archibald, and Quentin, and a second daughter, Ethel.

The now-recognized author of The Naval War of 1812 ran for mayor of New York City in 1886 but was defeated. President Benjamin Harrison had observed Roosevelt in action and appointed him to the Civil Service Commission, a relatively new oversight body. He performed so well at that post, enforcing civil service laws even when he was forced to tangle with supporters of patronage, that Democrat President Grover Cleveland reappointed him. From that post, he moved to the presidency of the New York City Police Board and a campaign to end corruption and once again assure the public that laws would be applied to each situation regardless of personal position or power.

Viewed as a strong leader and a reform-minded individual who demanded discipline and dedication in colleagues, McKinley appointed Roosevelt as assistant secretary of the U.S. Navy. Obviously, he believed in the importance of naval power for a nation bounded by the Atlantic and Pacific Oceans and the Gulf of Mexico (America) — hence that first book on the significance of naval power and commanders like Decatur and others. It would be Roosevelt who would respond immediately to the attack on the USS Maine, and it would be Roosevelt who would put Admiral Dewey on “high alert” for combat.

Indeed, war did come. And while it would only last four months, Roosevelt shed his civilian clothes and donned the uniform as a commander of the 1st U.S. Volunteer Cavalry and head for Cuba accompanied by his Rough Riders, a uniquely colorful group of volunteers from all walks of life, and they made headlines in an uphill charge reminiscent of Gettysburg’s Little Round Top known as the “Charge Up San Juan Hill.” Actually, it was Kettle Hill, but who corrects the newspapers?

The returning hero was poised for further action, and next week, we’ll move on up with him…

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