The rough riders joined in the capture of kettle hill and then charged across a valley to assist in the seizure of san juan ridge, the highest point of which is san juan hill. Roosevelt, theodore rough riders theodore roosevelt leading the rough riders during the spanish-american war, 1898 print created by kurz & allison. Teddy roosevelt and the rough riders july 1, 1898 before becoming president of the united states, theodore roosevelt was the assistant secretary of the navy. He resigned in 1898 to organize the rough riders, the first voluntary cavalry in the spanish-american war. Was fighting against spain over spains colonial policies with cuba. The most famous of all the units fighting in cuba, the rough riders was the name given to the first u. Volunteer cavalry under the leadership of theodore roosevelt. Roosevelt resigned his position as assistant secretary of the navy in may 1898 to join the volunteer cavalry. The unit consisted of men from all walks of life and ethnic backgrounds. Theodore roosevelt led the most celebrated military unit in the spanish-american war. The unit, dubbed rough riders, consisted of volunteers and took its name from a popular phrase of the time. 1 t0849240000 about rough riders 2 gay la motorcycle clubs imageheader t2125320000 1 t0850140000 rough riders archive 9 imageheader 117 t0454570000. Influence of new mass media on the conflict and the rhetoric utilized to rouse support for the war. Theodore roosevelts rough riders cavalry regiment serve as a model for how public perception of the war was shaped by rough riders that was purported to represent american ideals. Led by the fiery teddy roosevelt (1858-1919) and full of cowboys, athletes and other tough, courageous men, the rough riders were legends in the spanish-american war.