Stephen Gentry is in his second season as an assistant coach after joining the Fighting Illini staff in August 2019. 

He was instrumental in schematic changes implemented during the 2020 season that saw the Illini improve 73 spots in defensive efficiency and rise 45 spots in offensive efficiency, as Illinois ended the year ranked in the top 40 in both categories for the first time since 2011. 

Gentry reunited with Brad Underwood after spending two years at Gonzaga as director of operations for coach Mark Few. The Bulldogs had a stellar 65-9 record over Gentry's two seasons, winning back-to-back West Coast Conference titles and twice advancing to the second weekend of the NCAA Tournament.

Gonzaga went 32-5 in 2018, winning both the West Coast regular season and tournament championship, and made an NCAA Sweet 16 appearance. The 2019 Bulldogs, meanwhile, were 33-4 overall and a perfect 16-0 en route to the WCC regular season title. Gonzaga won the Maui Jim Maui Invitational, held the No. 1 ranking in the AP poll for a total of five weeks, and earned a No. 1 seed in the NCAA Tournament, advancing to the Elite Eight.

Gentry was alongside Underwood for four-plus seasons prior to his tenure at Gonzaga. He was at Stephen F. Austin for three years, Oklahoma State for one, and was part of Underwood's original staff at Illinois, as assistant to the head coach, during the spring of 2017 before departing for Spokane. Gentry's four seasons with Underwood saw their teams go a combined 109-27, including three conference championships and four NCAA Tournaments. 

Gentry has been on staff for five conference championship teams in the last six seasons, and part of teams that have participated in 10 of the last 12 NCAA Tournaments – including each of the last six years – recording a total of 11 Tournament wins. He also has contributed to three different teams that have had the number one offensive efficiency ranking in the country: Gonzaga in 2019, Oklahoma State in 2017, and Gonzaga as a player in 2006.

"I've said it often that Stephen has a great basketball mind, and he was a crucial piece to what we were able to accomplish at Stephen F. Austin and Oklahoma State," Underwood said. "I am excited to have him back on our bench after two incredibly successful years at Gonzaga with Coach Few. Stephen is gifted with Xs and Os and analytics and excels with player development. Given his familiarity with our system and our program, he w has provided a seamless transition for our players."

Gentry spent the 2017 season as director of player development at Oklahoma State, where the Cowboys won 20 games and advanced to the NCAA Tournament. Prior to OSU, Gentry was an assistant coach at Stephen F. Austin. The Lumberjacks went a combined 89-14 during his three seasons, winning three straight Southland Conference regular season and tournament titles to qualify for the NCAA Tournament all three years, twice advancing to the Round of 32. SFA went 32-3 in 2014, 29-5 in 2015, and 28-6 in 2016 for the winningest three-year run in Southland history.

Prior to SFA, Gentry spent six seasons at Texas A&M, including his final two as director of basketball operations under then-coach Billy Kennedy. That followed four years as video coordinator for former Texas A&M (now Maryland) coach Mark Turgeon. The Aggies won 129 games during his six season in College Station, participating in four NCAA Tournaments. Gentry came to A&M after one year as a video intern for the NBA's Miami Heat under Pat Riley.

During his coaching career, Gentry has worked with eight players who have gone on to play in the NBA. Among the notable players he has mentored include Khris Middleton at Texas A&M, Thomas Walkup at Stephen F. Austin and Jeffrey Carroll at Oklahoma State. 

Gentry played four seasons of college basketball at Gonzaga, lettering three years. During his career the Zags went 107-20, won four consecutive WCC titles and participated in four NCAA Tournaments, advancing to the second round three times and the Sweet 16 in 2006.

Gentry earned two degrees from Gonzaga, a bachelor's in sport management in 2005 and a master's in sport and athletic administration in 2006.