As Assistant Secretary of the Navy from 1897 to 1898, Theodore Roosevelt supervised the building of twenty-six new steel ships. After the explosion of the USS Maine, Roosevelt wrote: “If we will not fight for the blowing up of the MAINE... we are no longer fit to hold up our heads among the nations of earth.” Roosevelt became second-in-command of the First Volunteer Cavalry, known as the “Rough Riders,” in the Cuban campaign of the war. 

This portrait, by Charles Dana Gibson, demonstrates how Roosevelt fashioned his own image during the war. Instead of wearing an Army-issued uniform, he ordered one from Brooks Brothers, a high-end menswear store. This illustration accompanied his published memoir as a lieutenant colonel of “The Rough Riders” in the January 1899 issue of Scribner’s. Roosevelt’s fame served his political aspirations. President William McKinley named him as his running mate ahead of the 1900 presidential election.