A long three-story school of dark red-brown brick set on a grassy rise, its wings raised on a base of rough-faced stone and lit by tall banks of multi-pane windows under a slate roof with gabled ends. At the center stands a pale-faced entrance tower framed by striped brick piers and crowned by two turrets with copper ogee domes and finials. The tower's face is a grid of tall windows, round-arched in the upper rows, with carved shields and panels between the floors and a balustraded parapet; the main doors sit in a Tudor arch at the head of a broad flight of steps. A tall brick chimney rises behind the center of the building.
The site was acquired in 1922 to relieve crowding at McKinley and Cleveland high schools. It had been Picker Cemetery, also called Holy Ghost Cemetery, and removal of the graves began in October 1922. Rockwell M. Milligan designed the school; its cornerstone was laid on April 22, 1923, and it opened on January 26, 1925, at a cost of just under $1.5 million. Most of its first students and teachers came from McKinley, which became a middle school. The school took its name, its Rough Riders nickname, and its first yearbook title, BWANA, from Theodore Roosevelt, and its colors and the melody of its song from Harvard, his alma mater. Court-ordered busing began at Roosevelt in 1980–1981. A magnet program ran there from 1985 until 1993, when it moved to Soldan High School, and the building was renovated over two years in the mid-1990s.
