Roosevelt was the only public, English-standard secondary school in the Territory of Hawai‘i. It was initially composed of grades seven to eleven and housed in temporary quarters in an old, Normal School building that formerly trained teachers for Hawai‘i’s public schools. Honolulu students would typically go to Lincoln, then to Jefferson or Stevenson (both English Standard) and then to President Theodore Roosevelt High School. The school’s property encompasses a little over 20-acres in upper Makiki, in Honolulu. From 1883-1927, the site had been the home of Lunalilo Home.
A heated football rivalry began in 1933 between Roosevelt and nearby Punahou. Roosevelt seniors Lex Brodie, Rufus Hagood and Gibby Rietow responded by painting the blue pie sections of Punahou’s Pauahi Hall dome green. (At the time Roosevelt’s school colors were green and gold; out of deference for Leilehua High School, Roosevelt’s colors were changed to today’s red and gold in 1939.) The tradition continued until 1969, after which Roosevelt became a part of the O‘ahu Interscholastic Association and Punahou the Interscholastic League of Honolulu, and the two schools no longer played regular season games against each other.