[9] Simeon was founded in 1949, as Westcott Vocational High School in a building located at 8023 S. Normal Avenue.

It operated until the Kroger company donated a vacant warehouse, located at 8235 S. Vincennes Avenue, to the Chicago Public Schools in 1963.

[11] The Career Academy designation at the Chicago Public Schools is “a college-preparatory curriculum and career–focused education in different fields at each school.”[12] Key Career and Technical Education (CTE) programs at Simeon are, Each program provides the opportunity for students to gain direct knowledge and most earn industry-recognized certifications or college credit.

Simeon competes in the Chicago Public League (CPL) and is a member of the Illinois High School Association (IHSA).

Student-Athletes 2013, Simeon is the first Chicago public school to win four consecutive basketball state titles, and the second statewide.

More Simeon alumna have been selected in the Major League Baseball amateur draft, than any other high school in the state.

[26] Led by Jabari Parker and Kendrick Nunn, they won the 2012 Illinois Class 4A championship by defeating Proviso East High School.

The 68–64 win over far South Side rival Morgan Park High School was their eighth city championship.

[34] The day after his murder, then Chicago Mayor Harold Washington spoke to grieving students, denouncing gun violence in the city and promising a new gymnasium for the school, to be named in Wilson's honor.

[35] Afterwards, Ben Wilson's number 25 jersey was traditionally worn by Simeon's best player, until it was retired.

[36] Rose moved on to become one of the nation's top point guards in 2007 and eventually an NBA All-Star and league MVP for the Chicago Bulls.

Nick Anderson, Deon Thomas and Calvin Brock are Simeon alumni who wore that number at the University of Illinois in honor of Wilson.