[1][2][3] Wootten enrolled at Montgomery College and in 1951 began coaching baseball, football, and basketball at St. Joseph's Home and School for Boys, an orphanage in Washington, D.C.
[1][2][4][5] In 1956, Wootten was hired as a history teacher and the coach of the football and basketball teams at DeMatha Catholic High School in Hyattsville, Maryland.
Led by star player John Austin, the basketball team won its first conference title in 1961 and the national high school championship in 1962.
In 1965, Wootten made national headlines when his DeMatha team beat Lew Alcindor's Power Memorial Academy and ended its 71-game winning streak.
[2][6][7] Wootten has the second most wins as a head coach in the history of boys high school basketball, behind Robert Hughes.
Mike Brey, former head coach of the Notre Dame Fighting Irish men's basketball team, also played under Wootten.
[7] During his coaching career at DeMatha, located just two miles (3 km) away from his alma mater, he received job offers from North Carolina State,[12] Georgetown, and American, as well as interest from Duke, Wake Forest, and Virginia.
[5] Upon retiring, DeMatha hired former player and 1991 graduate Mike Jones who led the Stags from 2002 to 2021 after spending four seasons an assistant under Wootten.
[22][23] Wootten appeared in the 2020 documentary Basketball County along DeMatha alums Victor Oladipo and Adrian Dantley.