Walter C. Roberts was Masconomet High School’s first Varsity Football Coach, from the opening in 1959 to 1973 ("In Memoriam"). He led the team to numerous victories and perhaps his greatest legacy with the 1963 team, Masconomet’s only undefeated season (Williams).

Roberts graduated from Johnson High School in North Andover, and went on to play football as a tight end at The College of The Holy Cross from 1940-1941 ("In Memoriam"). He was an East College All-Star and played in the East-West Shrine game at Holy Cross. From 1942-1946, Walter served as an Air Force Tail Gunner in WWII with the 501 Bomber Group in the Pacific Combat Zone. He returned to Holy Cross and graduated in 1947. After briefly coaching at Andover, Belmont, and Methuen, he began his career at Masconomet with the opening in 1959 ("In Memoriam"). He was a Masconomet math, and later a physical education, teacher from 1959 to his retirement in 1982 (Pugh). In addition to being the head football coach, he also coached Masconomet varsity baseball with a recognizable 19 game streak from mid season 1962 to 1964 (Richardson). In addition to his successful career, Walt was also a father of seven (Richardson).

Roberts led the football team for 13 straight seasons with an accumulated record of 64-43-2 ("Masco to Dedicate Field in Initial Coach's Honor"). In 1980, he was inducted into the Massachusetts High School Football Coaches Association Hall of Fame as well as the Johnson High School Hall of Fame (North Andover, MA) in 1983 (Souza). In 1987, he was recognized by the College of Holy Cross for his achievements as a player himself and was inducted into the Holy Cross Athletic Hall of Fame ("In Memoriam").

Mr. Jim Pugh, a former coach of Masconomet football and overlapping teacher with Walt, describes Walt's coaching and teaching style as "old school" (Pugh). Roberts was known for being a strict and disciplinary coach, yet was adored and celebrated by his players (Pugh). Paul Richardson, a four-year quarterback for Walt and a member of the celebratory 1963 team commemorates his former coach, “Walt took us from being a bunch of kids to being men and that's what we loved,” (Richardson). Richardson also praises Walt as a coach expressing "he had an offense more elaborate than some colleges at the time," (Richardson).

In 2013, members of the 1963 squad reunited to celebrate the 50th anniversary of their undefeated season specifically their infamous Pentucket defeat (Williams). The 1963 team was "reliving the glory days" as stated by Dick Ray, and remembering their beloved coach who made it all possible (Williams).

Masconomet dedicated their football field in 1997 in hopes of capturing the achievement and legacy Walter Robert’s holds for both the school and the football program (Pugh).