Career
He played for the Saint Bonaventure Bonnies from 1996 to 2000 and was named to the Atlantic 10 All-Conference first team in his senior year. Winn played for Louisiana Salle Senior High School in Niagara Falls. Winn played for Saint Bonaventure.
In his freshman season, 1996-1997, he ranked second on the team with 13.3 points per game.
The following year, he averaged 12.2 points per game. In 1998-1999, Winn averaged 13.0 points and finished second in the nation with 3.5 steals per game.
He was suspended for the first six games of the season when he was arrested for getting into a fight with another student. After pleading guilty to misdemeanor assault, he was sentenced to three years" probation.
In Winn"s senior season, 1999–2000, he averaged 13.6 points per game and led the Bonnies in scoring.
He also had 103 steals, which set a school record. He was named to the Atlantic 10 All-Conference and All-Defense first teams. Winn finished his college career with 1,407 points, 349 assists, and 319 steals.
After college, Winn played professional basketball in several leagues in the United States and overseas.
In 2006, while playing for the Buffalo Rapids of the American Basketball Association, he averaged 25 points, 11 assists, and 4 steals and represented the Rapids in the American Bar Association All Star Game.