At time of annexation, there were 140 public schools, including industrial schools at Lahaina and Hilo, and 55 private schools (including one Japanese school.)
`Through the 1920s, more than half of the high school students in the Territory attended McKinley High School. Among its 1929 student body of 2,339, nearly one of ten students was (Caucasian) … 43% were of Japanese ancestry and 20% of Chinese parentage. Eleven percent … were Hawaiian or part-Hawaiian and 4 percent were Portuguese’. (Javonovich)
In the entire territory, there were four high schools: McKinley (the former Honolulu High School;) Hilo, established in 1905; Maui (1913;) and Kauai (1914). The Territory had a proportionally smaller high-school enrollment than any of the forty-eight states, Puerto Rico or the Canal Zone.
Unhappy that so many students came from homes where English was not spoken, Caucasian parents forced the first English Standard grammar school, Lincoln. Admission required a passing grade in an English proficiency exam. (Javonovich)
When the upper grades of Lincoln school became the nucleus of Roosevelt Junior High School, the English standard plan was carried over to that institution. (LRB) 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. When Roosevelt became a senior high school (President Theodore Roosevelt High School) – Robert Louis Stevenson Intermediate School taking over the Roosevelt junior high school grades. (LRB)
In 1937, the seventh, eighth and ninth grades were permanently removed to the Normal School building, reorganized as an intermediate school, and Roosevelt High remained as a school for tenth and eleventh graders until 1939 when it became a three year high school. (NPS)
Honolulu students would typically go to Lincoln, then to Jefferson or Stevenson (both English Standard) and then to Roosevelt.
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, an institution for the aged and infirm Hawaiian , whose creation was willed by the estate of Hawaii’s sixth king , William Charles Lunalilo.
Crowning a wide, grassy knoll is the Main, or administration, building of President Theodore Roosevelt High School , named in honor of the twenty-sixth US President.
This predominantly three-storied building with its tower and auditorium are of the Spanish Revival style with plain, cream-colored stucco walls, a symmetrically placed window, decorative arches and vents and a red tile roof. It is the only Spanish Revival building in an eleven-building complex.
The building was designed by Guy Rothwell and Marcus Lester and built of reinforced concrete in 1932. Its plan is generally H-shaped with slight modifications. Attached to the front of the shorter east wing in 1935 are a square tower, approximately 75-feet high, and to that, an auditorium.
The campus classrooms are loosely arranged in a generally horizontal formation on three graded levels of sloping topography. All other buildings, added after 1932, are two stories high and of contemporary design. (NPS)
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.)
After several years of costly vandalism on the eve of their games, the ‘Paint Brush Trophy’ was jointly created in 1948 by the student bodies of both schools as a peacemaking gesture. Thereafter, the winner of the annual Punahou-Roosevelt football game took possession of and proudly displayed ‘The Paint Brush Trophy.’
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. (Punahou)