A native of Verona, New York, Winterton grew up on a 100-acre dairy farm in a family that valued discipline and hard work. He was introduced to wrestling by his older brother Jim (presently in the National Racquetball Hall of Fame) in 5th grade and continued through junior and senior high school at Vernon Verona Sherrill (VVS). After high school, he attended junior college winning a Region III Championship for future North Carolina State Coach Bob Guzzo and SUNY-Canton ATC. After two years, Winterton transferred to Brockport State University where he started both his junior and senior years on a State Conference Championship team. In 1972, Winterton competed in the Small College Nationals in Owego, NY. He then returned home to teach Physical Education and coach wrestling at VVS High School for two years before becoming an assistant for Coach Guzzo at N.C. State from 1975 to 1977. In 1976 and 1977, Winterton helped the Wolfpack the win the ACC regular season championship. In 1976, N.C. State also won the ACC tournament championship. 

From 1977 until 1981, Winterton taught and coached wrestling at East Wake High School before moving over to Cary High School where, for over four decades, he led North Carolina’s most dominant high school wrestling program. Under Winterton’s leadership as head coach, Cary won 11 state tournament championships, eight state dual-team crowns, 167 tournaments (at one point #2 in the nation), 28 consecutive conference championships (31 total), and 265 consecutive home regular-season matches.  Winterton coached 42 different individual state champions, 32 High School All-Americans, two members of USA Wrestling’s High School Dream Team, and owns a career dual meet regular season 581-3 at Cary High School. Competing in the state’s largest division (4A), Winterton’s Cary teams boasted four or more state champions on five separate occasions. In 2003, Cary had seven state finalists and in 2008 had five individual state champions. Winterton stepped down as Cary’s head coach in 2010 but returned to coach the team from December 2019 through February 2021 following the unexpected passing of Coach Anthony Dunbar. Winterton’s overall dual meet record is 685-35 including records of 663-17 at Cary and 22-18 at East Wake. He was the North Carolina coach of the year ten times and named national coach of the year by the NHSCA (2007) and the NWCA (2009). In 2013, Winterton was selected one of the top 100 coaches from all sports in the 100-year history of the North Carolina High School Athletic Association. Coach Winterton has been inducted into the Cary High School Hall of Fame (1995), North Carolina Chapter of the National Wrestling Hall of Fame (2004), North Carolina High School Athletic Association Hall of Fame (2015) and National Federation of High School Sports Hall of Fame (2017). He is one of only three coaches (all sports) from North Carolina to be inducted into the NFHS Hall of Fame.