Drew Winston enters his fourth season as Triton College women's basketball head coach. He has guided the Trojans to 20-plus wins in each of his three previous seasons at the helm, including a 27-5 mark last season. The .844 win percentage was the best for the program since the 1983-84 season. That accomplishment led to Winston being named Co-Collegiate Coach of the Year in NJCAA Division I by the Illinois Basketball Coaches Association (IBCA).

Winston has coached a pair of NJCAA All-Americans, Monraia Wilson (2022-23) and Jordyn Coleman (2024-25) along with eight All-Region 4 selections. He has had two former Trojans move on to play at the NCAA Division I level, Coleman (Abilene Christian University) and Triton all-time leading scorer Trinity Barnes (Central Connecticut State University).

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 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.