Winters retired from the Argonauts on December 19, 2008, after six great years as a linebacker and defensive back. During his time with the Argonauts, he appeared in 82 regular-season games and eight playoff contests and was a member of the Argonauts' 2004 Grey Cup-winning team. In the 2007 season, he posted a career-high 38 tackles and led the team with 6 caused fumbles.
Winters grew up in the tough Herman Gardens project of Detroit, Michigan. When he was in middle school, gang violence began permeating the projects. For many, adolescence is one's search for acceptance. Like his head coach and many of his teammates, Winters sought acceptance in organized sports such as baseball and football rather than joining violent street gangs.
Although he escaped the vicious cycle of violence himself, his 19-year-old brother Malik was murdered in a drive-by shooting in 1998. Winters knows all too well the feeling of fear that one has walking the streets of Detroit and he is committed to working in the Greater Toronto Area community to ensure that its streets remain safe for all and that youth have a variety of life options from which to choose.
Winters hails from Detroit's St. Martin de Porres High School (closed 2005) where he won the MHSAA State Class C Football Title twice. While at St. Martin de Porres, Winters was an All-American in two sports football and baseball. Also, Winters was drafted in the tenth round in the 1992 amateur baseball draft by the Kansas City Royals. SMDP is the same school that produced fellow CFL player Kevin Glenn and former National Football League player Troy Kyles of the New York Giants.
During his college football years, Winters was a standout player at the University of Michigan from 1992-1996 in football and baseball. At the end of his college career he was drafted once again in the twentieth round by the Kansas City Royals. After leaving the game of football for a brief period of time, he spent several years playing in the Arena Football League, with the Detroit Fury and the Las Vegas Gladiators. While playing in the AFL, Winters won the 2002 "Hero award" awarded to the individual who exemplifies the most commitment to the local community and charity events.
Winters spends a great deal of time working with various organizations and is a great motivational speaker. He has an immeasurable impact on young people, and draws on his personal trials and struggles to illustrate his points.
Winters has been an active part of the Toronto Argonauts Stop the Violence campaign and has often spoken to students at different schools across Toronto. As of 2008, Winters has become a board member for the Stop the Violence initiative and continues to do countless community appearances in the GTA area and in the United States. 
During his career with the Argonauts, Winters made more than 900 appearances in the community. He was nominated three times for the Canadian Football League Players' Association Tom Pate Memorial Award, given annually to the CFL player who displays outstanding charitable efforts and superior community involvement and leadership.
Winters is the co-owner along with former Argonaut and native detroit resident Jerome Davis of Mississauga-based Last Play Training, a company designed to inspire youth to excel in both life and athletics. Also, Chuck is a certified teacher and holds a masters degree in Marketing.
- Toronto Argonauts profile
- Arena Football page
- StopTheViolence.ca profile
- Toronto Star article on Chuck Winters
- Chuck Winters retires
- Chuck Winters re-signs with Argos
- Last Play Training