His coaching journey commenced in 1993 as an assistant coach for Valparaiso University, a role he held for nine years, during which he also earned a master’s degree. In the 2002-2003 season, Drew advanced to Head Coach for Valparaiso, successfully guiding the team to a regular-season conference championship and securing an NIT bid. He immediately embarked on a comprehensive rebuilding effort, leading a short-handed team to an 821 record in his inaugural season. This period also saw Drew recognized as the Austin American Statesman’s Coach of the Year in 2010. Drew’s tenure at Baylor continued to be marked by consistent progress and significant achievements. By the 2013-14 season, Drew became Baylor’s all-time wins leader, a testament to his sustained impact. This historic achievement solidified Drew’s reputation for transforming and elevating college basketball programs and earned him the Big 12 Coach of the Year award. His recent success continued into the 2021-2022 season, where he once again led the team to a Big 12 Regular Season Championship, securing his third Big 12 Coach of the Year title.