Athletic Director Rocco DeMaio Jr. ‘86 Inducted into Hall of Fame in New Haven

Hopkins Director of Athletics Rocco DeMaio Jr. ’86 was recently inducted into the New Haven Gridiron Club Hall of Fame, an honor that recognized his distinguished football career that began on the Hill.

DeMaio was a standout three-sport athlete at Hopkins, excelling in football, basketball, and baseball. On the football field, he developed into one of the area’s top players, earning All-Fairchester League honors and serving as team captain. He scored 39 career touchdowns, including 18 during his senior season, and was among Connecticut’s scoring leaders throughout his career. He was also recognized as Hopkins’ Bill DeGenarro Outstanding Male Athlete.

DeMaio continued his football career at Trinity College, where he became a record-setting tight end. As a senior, he earned All-NESCAC and All-ECAC honors and was named Trinity’s Senior Offensive Player of the Year. His career included several school records for a tight end, including 143 receiving yards in a game against Williams and 583 receiving yards during the 1990 season.

“Football gave me much more than wins and losses. It taught me leadership, discipline, mental toughness, loyalty, how to handle adversity, and the importance of being accountable and understanding that you are part of something bigger than yourself. For me, football has always been a metaphor for life,” DeMaio said.

Baseball was an equally important part of DeMaio’s athletic career. As a senior at Hopkins, he helped lead the Hilltoppers to the program’s first Fairchester Athletic Association championship. At Trinity, DeMaio was a four-year starter at shortstop while also serving as the team’s closer. He captained the Bantams as a senior under head coach Bill Decker and finished his career as Trinity’s career saves record holder. 

DeMaio earned All-NESCAC and All-ECAC recognition in both football and baseball, and his two-sport collegiate career culminated with the George Sheldon McCook Trophy, Trinity’s top athletic award presented to the outstanding senior male athlete.

Following college, DeMaio returned to Hopkins. He spent 23 seasons as an assistant football coach on the Hopkins sideline under longtime head coach Tom Parr, helping mentor generations of Hopkins student-athletes.

DeMaio has served Hopkins for more than three decades as a coach, teacher, and administrator and has been Director of Athletics since 2015. He also currently serves as the School’s varsity baseball coach.

DeMaio was honored at a ceremony on September 9, 2026, at Woodwinds in Branford, Connecticut.