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Athletic Director Inducted to Hall of Fame
Hopkins Director of Athletics Rocco DeMaio Jr. ’86 was inducted into the New Haven Gridiron Club Hall of Fame on September 9, 2026, recognizing a distinguished football career that began on The Hill, continued at Trinity College, and has included more than three decades of coaching and service to Hopkins Athletics.
Rocco DeMaio Jr. — Hopkins School, Class of 1986, Trinity College 1991
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.
To read more about the Gridiron Club Hall of Fame and this year's inductees, click here.
Congratulations, Rocco, for this outstanding achievement!
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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.
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, where football remained an important part of his life. 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 currently also serves as the school’s varsity baseball coach.
His induction into the New Haven Gridiron Club Hall of Fame recognizes an accomplished playing career and a lifelong connection to a game that has shaped him both on and off the field.
“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.
Congratulations, Rocco, for this outstanding achievement!
Hopkins is a private middle school and high school for grades 7-12. Located on a campus overlooking New Haven, CT, the School takes pride in its intellectually curious students as well as its dedicated faculty and staff.
Hopkins School admits students of any race, color, national and ethnic origin to all the rights, privileges, programs, and activities generally accorded or made available to students at the school. It does not discriminate on the basis of race, color, national and ethnic origin in administration of its educational policies, admissions policies, scholarship and loan programs, and athletic and other school-administered programs.