About Winston Bennett
Born 1965. Winston Bennett is an American basketball player and basketball coach.
Winston George Bennett III (born February 9, 1965) is an American former professional basketball player and coach.
High school and college career A star at Louisville Male High School, Bennett was named "Mr. Basketball" for the State of Kentucky in 1983. He also earned Parade Magazine All-American and McDonald's All-American honors, sharing MVP honors with Dwayne Washington.
Bennett played collegiately at the University of Kentucky where he wore #25 and was known as "Steady Bee". As a freshman in 1983β84, Bennett appeared in 34 games for UK, averaging 6.5 points in 19 minutes per game as the Wildcats reached the Final Four, losing to Georgetown, 53β40.
The following season, he averaged 7.2 points in nearly 20 minutes per game to help UK to the West Regional Semi-Finals. In 1985β86, his junior season, Bennett was named to the All-NCAA Regional Team and the SEC All-Conference Team after averaging 12.7 points and 7 rebounds per game. Playing under first-year coach Eddie Sutton, Bennett shot better than 50 percent from the field helped lead the Wildcats to a 32β4 record.
After red-shirting in 1986β87 to rehab a serious knee injury, Bennett served as team captain and averaged 15.2 points and 7.8 rebounds per game as a senior during the following season, again earning All-SEC honors. Along with teammate and future NBA player Rex Chapman, Bennett helped lead the Wildcats that season to their 37th SEC title with a 27β6 record. The Wildcats were ranked as the 6th college basketball team in the nation by the Associated Press and UPI and secured the number two Southeast Conference seed in the 1988 NCAA Men's Division I Basketball Tournament. His best year as a pro came during his rookie season with the Cavaliers when he appeared in 55 games and averaged 6.1 points per game.
Coaching career
After his professional playing career ended, Bennett served as an assistant coach under Rick Pitino at the University of Kentucky from 1995 to 1997 and, later, under Pitino, with the Boston Celtics, during the 1997β98 NBA season.
In 1996, while an assistant at Kentucky, the Wildcats won the NCAA Championship, defeating Syracuse, 76β67. The following season, UK finished as the runner-up, losing to Arizona in the championship game, 84β79.
In May 2000, he was named head men's basketball coach at Kentucky State University, a Division II university in Frankfort, Kentucky. In his first season with the Thorobreds, he led the team to a conference championship.
But on November 6, 2003, less than a week before the 2003β04 season was scheduled to begin, Kentucky State fired Bennett for allegedly hitting a player. According to an Associated Press report, "senior guard Ricky Green filed a complaint with the Franklin County attorney's office, accusing Bennett of striking him in the face during practice." According to the AP story, Bennett expressed regret about the incident, saying "If there was ever a time when I wish the hands of time could be turned back, it is right now." Bennett was 44β43 in three seasons at Kentucky State.
In May 2007, Bennett was named the head men's basketball coach at Mid-Continent University, an NAIA school in Mayfield, Kentucky. In 2007β08, the Cougars went 11β21, finishing ninth in the TranSouth Athletic Conference.
On June 17, 2013, Bennett resigned his position as head coach at Mid-Continent. His record at six seasons at MCU was 91β103.
In 2014 Mid-Continent University laid off all its employees and made plans to close following the end of the school year.
Personal life Bennett and his wife Peggy reside in Louisville. After his coaching career, he joined Louisville-based insurance agency Van Zandt, Emrich & Cary Inc.
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Important facts
People in Winston Bennett's life
Named in this biography and alive at the same time
Contemporaries
People whose lives overlapped Winston Bennett's
Frequently asked questions
Who is Winston Bennett?
American basketball player (born 1965)
When was Winston Bennett born?
Winston Bennett was born on 9 February 1965 in Louisville.
What is Winston Bennett's occupation?
Winston Bennett is a basketball player and basketball coach.
What nationality is Winston Bennett?
Winston Bennett is American.
Sources & further reading
Cite this page
APA: Biography.guide. (2026). Winston Bennett. https://biography.guide/winston-bennett/
MLA: "Winston Bennett." Biography.guide, https://biography.guide/winston-bennett/.
Chicago: "Winston Bennett." Biography.guide. https://biography.guide/winston-bennett/.
Data last updated: 2026-09-20 Β· Spot an error? Report a correction.
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