Our school, originally known as Westcott Vocational High School, was established in September of 1949 at 8023 South Normal Avenue, Chicago, Illinois. The Westcott building on Normal Avenue was occupied by the Calumet High School until 1926. From 1927 to 1933, it was known as the Westcott Junior High, in honor of Oliver Spink Westcott. With the elimination of the Junior Highs in Chicago, the building became a branch of Calumet High School remaining as such until 1942. During the years of World War II, the United States Navy set up a training center in the Chicago Vocational High School building at 2100 East 87th Street, and that high school was relocated to the Westcott building. Chicago Vocational High School occupied the building until June of 1946, leaving it to move back into their own building on 87th Street after the Navy withdrew.
In September of 1946, the Westcott Continuation School took over the building. It continued as such until 1948, when a small group of vocational high school students were admitted. Due to an ever-increasing vocational high school membership, the Continuation school department was moved from the Westcott building and was known as the Princeton Branch of Westcott Vocational High School. In 1962 the Princeton Girls were moved into Westcott Vocational High School and the boys into the Tilden building.
In 1963, the Kroger Company donated its warehouse at 8235 South Vincennes Avenue to the Board of Education for the cost of $1, and after the renovation of the third floor, the Westcott Vocational High School and Girls Continuation School moved there in December of 1963. In September of 1964, the name of the high school was changed to Neal F. Simeon Vocational High School, honoring Neal F. Simeon.
Simeon grew in enrollment; it became known as one of the best-run schools in Chicago. Tragedy and national notoriety occurred with the passing of student Ben Wilson in November of 1984. The student body was deeply affected by the loss of the superior basketball player, and Mayor Harold Washington visited the school, promising a new physical education building. The Ben Wilson Gymnasium opened in 1989.
The school name was changed from Simeon Vocational High School in September of 1998 to Simeon Career Technical Academy. In 2003, the name changed to Simeon Career Academy to make way for a brand-new school building. The address was changed from 8235 S. Vincennes Ave. to 8147 S. Vincennes Ave.
On June 26, 2005, a retirement celebration was held at the school for retiring Principal John E. Everett, the driving force behind the new building's construction. Mr. Everett was a fixture at Simeon for thirty years, working as football coach, athletic director, the dean of discipline, assistant principal, and eventually the principal of Simeon from 1994 to 2005. During that retirement ceremony, Chicago's Mayor Richard M. Daley instructed that renamed a portion of Vincennes Avenue between 80th and 83rd Streets be henceforth known as John Everett Drive. On the same day, a dedication of the new Alvin R. Scott, Sr. Athletic Center was made in honor of the late Coach Scott, the legendary athletic director and head football coach of Simeon.