Theodore Roosevelt High School has served as a valued educational center and a cultural inspiration for generations. It began with a very few students who attended school in a one-room frame structure erected in 1908 at Twelfth Avenue and Massachusetts Street.

Mr. Everett D. Simpson was the first teacher employed. At that time there was another school at Fourteenth Avenue and Connecticut Street. In 1912, the pupils of these two centers were moved into the new Froebel School at fifteenth and Madison Street.

To meet the new demands of the growing Gary population, a school for primary children was opened at Twenty-First Avenue and Adams Street in 1915.  To this center, Mrs. Elizabeth Lytle and a group of primary children were transferred from Froebel School.  The next year three additional teachers were employed.

In 1921, the school was moved to the present site on Twenty-Fifth Avenue and Harrison Street. Mr. Z.D. Lenoir was appointed Principal. This school was called the Roosevelt Annex.  There was another school, Roosevelt, on the front of the same site at this time. This school was housed in a group of portable structures, and Mr. James Stanley was the Principal.  Both schools had been named for Theodore Roosevelt, the twenty-sixth president of the United States.

In 1923, Mr. Lenoir resigned and Mr. Stanley became principal of the two schools. Mr. Everett D. Simpson became the assistant principal in charge of Roosevelt Annex.  The east building of the present group of brick structures was built in 1923, and the west building was built in 1926.

In February 1925, during the administration of Mr. Stanley, the first year of high school was added with an enrollment of nineteen. Mr. F. C. McFarlane became assistant principal of Roosevelt Annex in 1927. He was made principal in 1929.

In 1930 Roosevelt Annex, now officially named Roosevelt School, became a commissioned high school and was granted its first diploma in June of that year.  Roosevelt was admitted to the North Central Association of Schools and Colleges in 1931.

In 1933, Mr. McFarlane resigned the principalship of Roosevelt. In August of the same year, the high school section of Pulaski was united with Roosevelt, and Mr. H. Theo Tatum, who had been principal of East Pulaski School became principal of the combined unit.

Mr. H. Theo Tatum retired in 1961 and was succeeded as principal by Mr. Warren Anderson, who served until July 1970. Beginning in the fall of 1970, Mr. Robert E. Jones became principal.  He served from that time until 1990.  Mr. David Williams served from 1990-1992 as head principal. Mr. William Reese, Jr. served as head principal from 1992 until the fall of 1997.  The next principal, Mr. Edward B. Lumpkin, Sr., began his tenure as head principal in 1997. Mr. Lumpkin retired from this position on June 30, 1999. Mr. Marion Williams began his term as principal during the 1999-2000 school year.  Mr. Williams is presently serving as Instructional Leader and Principal of Roosevelt High School.

Theodore Roosevelt High School remains the first and only school built exclusively for the African-American community in the city of Gary.  Many people, from all walks of life, are extremely proud to claim Roosevelt High School as their alma mater.  It has been and will continue to be an effective and positive influence in the community.