Bob was a three-year starting first baseman at Camden High School from 1947 to 49. He was named to the All Group Four Team in ' 48 and ' 49 batting over .300 and leading Camden in 1949 with a .347 average, and in RBIs and home runs. Following graduation, he signed with the Phillies, but after two seasons, he enlisted in the U.S. Coast Guard during the Korean War.

Following his discharge, he turned down the opportunity to return to the Phillies because of family commitments. He went on to play independent baseball in the Camden County League winning championships with M and S Machine in 1956 and Schillig's Black Horse Farms in 1957.

Winters retired as a major in the New Jersey State Police and spent time in the N.J. Attorney General's Office and as director of police for two years in Camden.Bob lives with his family in Turnersville, NJ.