In February 2020, the Distressed Unit Appeal Board voted to close Roosevelt after a series of burst pipes throughout the winter of 2019 left the school in need of expensive repairs.

Roosevelt was part of the Indiana High School Athletic Association as a member of the Northwestern Conference.

After portable classrooms were relocated to Twenty-fifth Avenue and Harrison Street the school was named the Roosevelt Annex.

The new building was designed by architect William Butts Ittner, constructed in 1929, and dedicated as Roosevelt High School in April 1931.

The Gary Roosevelt was developed during the early decades of the twentieth century as part of William Wirt's Gary System of education, which offered vocational training and college preparatory classes to high school students, as well as extracurricular activities and athletic programs.

[2] Beginning in 1915, as Gary's population grew, some African American students transferred to portable classrooms on Twenty-first Avenue and Adams Street, as well as other segregated schools.

The portable classrooms were moved in 1921 to Roosevelt High School's present-day site at Twenty-fifth Avenue and Harrison Street.

William Wirt, the city's first Superintendent of Schools, developed the Gary System during the early decades of the twentieth century.

The Gary System offered vocational training and college preparatory classes in the city's high schools, as well as extracurricular activities and athletic programs, an innovative idea that influenced the development of modern education.

[5][14] Donna Henry served as principal from the fall of 2013 until the spring of 2018, and under her leadership, the school received its first A grade from the Indiana Department of Education.

Ian Miller succeeded Donna Henry as principal beginning the fall of 2018, and shortly resigned in January 2019.

Shortly after, Gary Community Schools announced that Theodore Roosevelt would be closing indefinitely, and students would be merged with West Side Leadership Academy.

[2][5] Architect William Butts Ittner of Saint Louis, Missouri, designed the main, Colonial Revival-style high school facing Twenty-fifth Avenue.

The high school's landscaped grounds included playground equipment, a track, and a football field.

The high school's original interior featured terrazzo flooring, as well as glazed ceramic block and plastered walls.