Miles H. Hubbard, Jr. ’57 P’82 passed away Sunday morning, July 28th, after a relatively brief, but valiant battle with cancer. He died peacefully at his home with his beloved wife Janet and children by his side. 

Miles was a fixture of Trinity-Pawling, an embodiment of the ideals of the School that he loved. He entered Trinity-Pawling as a sophomore in 1954. During his three years as a student at Trinity-Pawling, he accomplished significant achievements as an athlete, student, and citizen. He amassed 8 varsity letters in football, basketball, track, and baseball. In his senior year, he was captain of the football and track teams and won the most valuable player award in both sports. Also in his senior year, he was an integral member of the varsity basketball team which had a remarkable season finishing with a 19-1 record which was the best in school history; the team was named Tri-State League champions and was recognized as the top team amongst New England prep schools.  Miles was a member of the Student Council and elected a Prefect in his senior year.

After graduating from Trinity-Pawling he matriculated at Middlebury College where he was a member of the varsity basketball team. Post-college, Miles served his country as a 1st Lieutenant in the U.S. Army and a Captain in the U.S. Army Reserves. 

In 1964, Miles returned to Trinity-Pawling as a teacher and coach. In 1973, Miles became the athletic director while also continuing to teach and coach. As the varsity basketball coach, Trinity-Pawling won 11 Tri-State Championships and amassed a .700 winning percentage. Miles also assisted head coach Chris Kelly ’81, when Trinity-Pawling won the New England Championship with an undefeated record in the 1993-1994 season. 

In 1989, Miles joined the Development Office as the Director of the Annual Fund. Later he would also serve as a liaison to the Development Office and was particularly adept at reconnecting alumni to the School.

Miles has been inducted into the Trinity-Pawling Athletic Hall of Fame four times: once, individually in 2001; once as a member of the 1956-1957 Varsity Basketball Team in 2007; once as a coach of the 1977-78 baseball team in 2009; and, once as a coach of the 1993-1994 Varsity Basketball Team in 2014.

Miles retired as Athletic Director in 2001 after 37 years of loyal, dedicated service to the School. In 2005, he returned to serve the school in the equipment room of the gym where he continued to provide sage advice to coaches, young and seasoned alike, as well as lessons of accountability to scores of students who were likely oblivious to the lion in their midst. 

Miles is survived by his devoted and lovely wife, Janet Hubbard P'07. He is also survived by his son, Jeff ’82,  daughter-in-law Julie Hubbard, and three grandchildren (Colin, Giles, and Ginger); his daughter Sharon Hubbard Gaines and her husband Jim Gaines; stepdaughter Alicia Hynes, her husband Tom Hynes, and their children Derek and Dylan Hynes; and stepson, Philip Ignarra '07.  He was predeceased by his ex-wife, Terry. 

On his senior page of the yearbook in 1957, Miles included a quote from Cicero which reads, "A man's own character is what most becomes him." Evinced by the thousands of students, coaches, teachers, and alumni whose lives have been indelibly impacted by the lessons of responsibility, accountability, and perseverance that Miles imparted by his life of dedication and service to the School, his life revealed an abundance of character that truly became him.

As mentioned in his obituary, services will be held at All Saints' Chapel on the Trinity-Pawling School campus on Sunday, August 11, 2019 at 11:00 AM followed by a reception near Hubbard Court in Trinity-Pawling's Smith Field House.   

Well Done, Thou Good and Faithful Servant.