The school was built in 1908 as a one-room building on 12th Avenue and Massachusetts Street. It combined with another institution and moved to Fifteenth and Madison Street, renamed as the Froebel School. An elementary school was added in 1915 as Gary's population grew. Some Froebel students transferred to the new school. The school moved again in 1921, to Twenty-fifth Avenue and Harrison Street, as the Roosevelt Annex. In 1923, the principal, James Stanley, assumed duties at another school named Roosevelt while also running the Annex. In 1925, the Annex began offering secondary school courses. In 1929, F. C. McFarlane succeeded Stanley as principal and a year later the school was accredited, graduating its first high school class.
Roosevelt was admitted to the North Central Association of Schools and Colleges in 1931.
In 1933 McFarlane resigned the principalship of Roosevelt. In August of the same year, the high school section of Pulaski was united with Roosevelt, and H. Theo Tatum, who had been principal of East Pulaski School became principal of the combined unit.
Tatum retired in 1961 and was succeeded as principal by Warren Anderson, who served until July 1970. Beginning in the fall of 1970, Robert E. Jones became principal. He served until 1990. David Williams served from 1990-1992 as head principal. William Reese, Jr. served as head principal from 1992 until the fall of 1997. The next principal, Edward B. Lumpkin, Sr., began his job as head principal in 1997. Lumpkin retired from this position on June 30, 1999. Marion Williams succeeded Lumpkin and served as principal from 1999 to 2005. Charlotte Wright was principal of Roosevelt High School from 2006 to 2012. Terrance Little was hired as principal in May 2012, but resigned in February 2013.
Roosevelt High School remains the first and only school built exclusively for the African-American community in the city of Gary.
Effective at the beginning of 2012-2013 school year, the Indiana Department of Education, under the authority of Public Law 221, took control of Roosevelt High School away from the Gary Community School Corporation due to substandard academic performance. The state contracted with EdisonLearning, a Tennessee based for-profit company, to operate the school for the next four school years. Edison renamed the school Theodore Roosevelt College & Career Academy.