Winters attended academic and athletic powerhouse Archbishop Molloy High School in Queens, New York, graduating in 1970.

On April 18, 1976, in the first playoff series of his NBA career, Winters scored 33 points and recorded 5 assists in a 107–104 Game 3 loss against the Detroit Pistons.

[3] The following season, on December 16, 1977, Winters scored 24 points and made a game-winning jumpshot during a 152–150 triple overtime win against the New York Knicks.

[5] Overall, he had a productive nine-year career that included two appearances in the NBA All-Star Game and six in the playoffs, and was a fan-favorite during the years that the Bucks struggled through immediately following the aforementioned Abdul-Jabbar trade.

[6][7] In a 2005 interview, Chicago Bulls superstar Michael Jordan singled out Winters as the best "pure shooter" in history, claiming that "he had the most beautiful stroke of all the people whom [he could] think of.