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The first school building in Roosevelt was started in 1903. It was a two-story frame structure in the same block and a little to the south of the present grade school building. School was held beginning in September of the same year.
According to incomplete records, the first term was only a three-month term, taught by A. J. Stoop in the Presbyterian Church until they moved into the building. Nothing has been found on the year 1903-04, but it thought that there were probably two or three teachers.
The following year (1904-05), there were four teachers with Tom Flanery as principal. Some think that the school was taught by three women in succession: the last being Mrs. Stoops.
Sometime after 1907, in order to make room for a new brick building, the first building was moved west into the business district after being purchased by Mr. A. D. Root as a home for his family. The building still stands across from the bank building on Main Street. Fields Montgomery was superintendent at this time.
In 1909 a two story brick building with basement was erected. The first brick building, two stories with five or six classrooms, was first used in 1909-10, during the year when Dr. E. E. Dale was superintendent. There were five teachers at this time, and the number grew slowly but steadily until it reached 12 teachers in 1929-30. Since then it has ranged between 12 and 17.
In 1953 the former two-story brick school was torn down, and the more modern grade school took its place. It was completed in January 1954. Since then the junior and senior high schools have been on both sides of the highway in the north part of town.
The Roosevelt Senior High School Building was completed in 1930. Unfortunately, it burned sometime in the fall of 1946. It was almost completely rebuilt when a storm tore it down again; it was finally completed in September 1947. The high school students attended the two-story brick building, and the elementary students went to school in some of the churches’ classrooms and in the Hagemeier Building. Senior Graduation Exercises were held in the Baptist Church in May 1947.
The Arts-Crafts Building housing the Roughrider Gym was completed in 1936. Douglas Separate School was completed in 1937-1938 and was maintained by Roosevelt Schools for a good many years for Negro pupils in first through eighth grades. Eva Moore was one of the teachers at Douglas School. The stone building still stands in the west part of Roosevelt.
The Roughrider Fieldhouse and Roughrider Stadium were as completed in August 1952. The Agriculture Industrial Arts Building was completed in April 1954.
The Cafeteria and the math and science classrooms were added onto the High School Building on the north in 1967 to provide additional space and better facilities for the students.
In 1978 the new metal Roughrider Gym was constructed just west of the High School Building. District, Regional, and Area Basketball Tournaments were held there because of the size of the building.
Rather early, Roosevelt became a twelve year accredited high school. By 1935 it offered 19 units and reached 25 in 1940. At this time there were four years of vocational agriculture and home economics offered. Business courses and the usual academic courses were provided.
“On You Riders” was selected as the school song. Red and white were the school colors as far back as 1928-29. The Roughrider was chosen as Roosevelt's Emblem in 1929. Art, music, band, 4-H, F. F. A., F. H. A., science club, academic teams, football, baseball, and basketball were some of the extra curricular activities offered the students. These young people won many awards in the name of their school, but above all, they maintained a healthy attitude toward work and the rewards of fulfillment.
Originally District No. 7, Roosevelt became Con. 7 in 1929. Districts 58 (Withrow or Rusler) and 61 (Singing Valley or Hiawatha), north and northeast of Roosevelt, were part of the original consolidation. Since then Con. 5 (Cold Springs) was annexed as were parts of 42 (Christian or Babbs Memorial), 43 (Prairie Dell), 57 (Rainey Mountain), 59 (Union) in 1942, 60 (Pleasant Valley, also known as Frog Pond), 67 (Fairview), 68 (Gladson), 85 (Star Valley), 109 (Koonkazachey), and Con. 8 in 1957. Con. 10 (Cooperton) was added when the high school closed in 1965, and the grade school in 1971.
Superintendents have been George Hetzel (1907-09); E. E. Dale (1909-10); Clyde M. Howell (1910-12); followed by his brother, Charles P. Howell (1912-14); A. J. Stoops (1914 to 1915 or 1916); J. B. Conrad (1916-17); T. N. Delbridge (1917 to 1918 or 1919); L. Edwards (1919-20); H. S. Witt (1920 to 1922 or 1923); George A. Comstock (1923-25); I. C. Gunning (1925-30); G. S. Saunders (1930-34); Bill Kobus (1934-45); T. E. Lauderdale (1945-46); Elvoy Owens (1946-47); Henry Dacus (1947-56); J. Carl Fleming (1957-58); Ray Beavers (1958-59); Gene McPhail (1959-62); Jerry Doyle (1963-65); Edward L. Huey (1965-68); Tony Risinger (1968-69); Melvin Krewall (1969-72); Allen Zisman (1972-75); Philip D. Williams (1975-85); Mike Southall (1985-89); Gary Swart (1989-90); Ron Craig (1990-91); Charles Lewis (1991-92); and Odalee (Bullock) Craighead (1992-93).
High School principals have included: Tom Avants (1956-58); Mrs. George A. Comstock, Mrs. Rosa Cooksey, A. T. Edmondson, Fred Fleming, Lillie Mae Ford, Bruce Greenshields, Mrs. J. R. Harp, Fern Hooker, Lloyd Johnson, H. C. Jones, T. E. Lauderdale (10 years), Lillie Roberts, Terry Thompson, M. L. Sims, Floyd Roach, James Daniels, Kelley D. Hayes, James Gilmartin, and Odalee (Bullock) Craighead (1992-93)
Roosevelt Schools, Con. Dist. #7 consolidated with Snyder Schools and closed the doors in May 1993.