Drew Winston begins his third season as Triton College women's basketball head coach. A Triton district native, Winston was born and raised in Maywood, where we attended and graduated from Proviso East High School.
 
After attending Grambling State University in Louisiana, he returned home to the Chicago area where he found his love for coaching. In 2013 Winston was hired as the JV head coach at St. Joseph High School in Westchester. His passion for the game instantly changed the culture of St. Joseph girls basketball. Winston became one of the most successful JV coaches in school history. He went on to win several games and tournaments that year in addition to a GCAC conference championship. The following year Winston was promoted as varsity head coach of the St. Joseph girls basketball program. In his second year as varsity coach in 2016, Winston led the Chargers to the IHSA Class 2A state finals where they placed fourth. It was the first time that St. Joseph, a school known for its success on the boys side, had their girls team reach downstate. Over the next several years at St. Joseph, Winston would go on to achieve consecutive Illinois Basketball Coaches Association (IBCA) Coach of the Year awards (2016 & 2017) four regional titles, along with a sectional and super sectional title. 

In 2021, St. Joseph closed down and the following season Winston begin coaching at Hope Academy in Chicago. He had an amazing one season at Chicago Hope as Winston was able to place six graduating seniors into college, win over 25 regular season games and go undefeated in conference. His squad in 2022 won the conference, regional and sectional championships. In addition, Winston claimed his third IBCA Coach of the Year award.