 A 6-foot-8 forward with a 3-point shot, Wingfield had a stellar high school career at Westover, where he led his team to 4 straight state championships, earning him McDonald's All American team honors in a class considered to be one of the best national high school classes ever; the class included Randy Livingston, Jerry Stackhouse, Rasheed Wallace, Rashard Griffith, Darnell Robinson and others.He started on the four state-championship teams, even as a freshman.Wingfield fathered three children while in high school.