Theodore Roosevelt’s ranking in the top tier of beloved American veterans parallels his top-tier ranking (fourth or higher in polls of historians) among U.S. presidents. The great affection for Roosevelt as a veteran is a product of his heroic battlefield performance in Cuba in 1898 and his extremely successful efforts to bolster U.S. military power between 1897 and the end of his life in 1919, along with his exemplary character, endearing personality and other monumental accomplishments.
Soon after the Spanish-American War broke out in the spring of 1898, TR resigned from his position as assistant secretary of the Navy to organize and lead into combat a regiment of soldiers, the 1st U.S. Volunteer Cavalry. On July 1, 1898, Roosevelt’s “Rough Riders” joined other U.S. Army regiments in driving entrenched and well-armed Spanish forces from the San Juan Heights. Notwithstanding his innumerable subsequent achievements, Roosevelt would never cease to remember that July day as his “crowded hour,” as “the great day of my life.”
In the aftermath of Roosevelt’s heroic victory, the entire U.S. chain of command in Cuba recommended the colonel for the Medal of Honor. These officers’ recommendation was denied due primarily to the incompetence and the hostility toward TR of Secretary of War Russell Alger, whose department’s many serious blunders Roosevelt had criticized. This glaring injustice was at long last rectified when Roosevelt was posthumously awarded the Medal of Honor by President Bill Clinton during a ceremony in the Roosevelt Room of the White House in 2001.
As president, Roosevelt built up the U.S. Navy, making it the world’s second most powerful, and, to the great benefit of the United States and the world as a whole, managed to institutionalize a naval building program for the long term. The 14-month world cruise of Roosevelt’s Great White Fleet proved to be both a magnificent spectacle and a brilliant diplomatic maneuver, and has undoubtedly contributed even further to his standing as a particularly beloved veteran.
– William N. Tilchin, history professor at Boston University, author of “Theodore Roosevelt and the British Empire: A Study in Presidential Statecraft,” and editor of the quarterly Theodore Roosevelt Association Journal