Remembering Hugh B. Caldara

Former Gunnery teacher, coach and Athletic Director Hugh B. Caldara, 73, of Stonington, Connecticut, passed away on Thursday, October 18, following a battle with cancer. He is survived by his beloved wife, Joanne Caldara, who lived with him in the Gatehouse on campus during his Gunnery years.
A memorial service will be held in celebration of Caldara's life at Calvary Church, 27 Church Street in Stonington, CT on Saturday, November 17, 2018 at 2:00 PM. To view his full obituary, please visit the Dinoto Funeral Home website here.

The Gunnery community will remember “Cal,” as he was known to his colleagues, students and those he coached during his 37-year tenure at the school, twice over the upcoming months. First, on Saturday, February 9, 2019 at our Alumni Hockey Game, we will dedicate a jersey to Cal that will hang above the Girls Hockey bench. Details will be posted on our website here as they become available.

Then, as part of Alumni Weekend, on Saturday, June 8, 2019, we will hold a memorial service followed by an opportunity for people to gather and share stories about Cal. We will share more details on our website once they are available.

Cal joined The Gunnery in 1977 as a history teacher and Head Football Coach. He went on to teach a variety of courses, including Ethics, Public Speaking, U.S. History and U.S. Foreign Policy, and was always one of the most popular teachers among the students. As a coach, he was revered for leading The Gunnery’s football team to more than 100 wins, and helping to lead the girls varsity ice hockey team to multiple New England championships. In his 37 years with the school, he served as a teacher, coach, dorm parent, advisor and Athletic Director.
Ed Small, a member of the math faculty and The Anne S. and Ogden D. Miller Senior Master, and his wife, Peg Small, The Gunnery’s Registrar, both joined the school at the same time as Cal. Ed Small remembers him as someone who was deeply committed to the school and his students. “U.S. foreign policy was his first love, but he’d teach anything. He would do anything you asked him to do for the school, and he did,” he said.

“If you’d get him talking about football, he’d forget everything else. He knew everything – professional, college, prep school. He was always well-prepared,” said Small, who was the JV football coach, and an assistant coach for varsity football at the time. What made Cal successful as a football coach, he said, was that he “taught his students how to play, how to win, and how to believe in themselves.”

The Alumni Association inducted Cal into The Gunnery Hall of Fame, issuing a citation in 2014 that read in part: “While he had a hand in many endeavors, the teaching of football was one of his strengths. Hugh made every player feel that they could make a difference and believe that they could win. He missed very little when it came to preparing for a game. He set the bar high for them, but he set it even higher for himself.”

Born in Buffalo, New York, on September 26, 1945, Cal was a graduate of Taft School and Coe College in Cedar Rapids, Iowa, where he majored in history and English. From 1969 to 1971, he served in the U.S. Navy. He went on to earn a degree in secondary education from the University of Wisconsin at Madison, and master's degrees in history from the Wesleyan University and maritime history from the Munson Institute at Mystic Seaport.

Prior to joining The Gunnery, Cal was a teacher, coach and dorm master at Nyack Boys School in Upper Nyack, New York, and Kingsley Hall School in Westbrook, Connecticut. He was head of the History Department at St. John’s Military Academy in Delafield, Wisconsin, where he also taught U.S. history, coached varsity track and hockey, served as defensive coordinator for football, and was the head dorm master for 48 boys.

“Hugh will be missed by generations of alumni whom he helped to shape as a teacher, coach, and advisor. He was a consummate triple threat, a dear and faithful friend to many in our community,” said Head of School Peter Becker, who shared a tribute to Cal at School Meeting on Monday. It was written by Associate Dean of Students and Head Boys Hockey Coach Craig Badger and published in the Bulletin upon Cal’s retirement in 2014:

“Legendary faculty members are part of the folklore of every boarding school. They are known for their personality as much as they are for their impact in the classroom, dorm, or athletic field. They are beloved by students and peers alike for who they are, as much as for the work they do,” Badger said of his friend and colleague. “Cal worked to foster an awareness of the world beyond The Gunnery’s walls. However, it is in the hearts of those who know him where Cal will truly be remembered.”

Alumni and friends are invited to share their remembrances with the school community online at www.gunnery.org/RememberingCal.

The Gunnery

gps address: 22 Kirby Road, Washington, CT 06793
mail address: 99 Green Hill Road, Washington, CT 06793
tel: 860-868-7334
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Founded in 1850 by abolitionist, educator, and outdoorsman Frederick Gunn, The Gunnery is a coeducational college preparatory boarding and day school for students in grades 9 through 12/post-graduate. Dedicated teacher-mentor-coaches challenge students to reach their full potential in a home-like setting where character and citizenship are valued as much as intellect and achievement. Individualized attention and high expectations help young learners develop not only the skills and confidence they will need in college, but also the moral compass and love of learning that will serve them well in life. The school attracts ambitious, academically curious students who will both shine as unique individuals and thrive as contributing members of a deeply connected community. By the time they graduate, Gunnery students have become well rounded, grounded young adults with a sharpened sense of who they are and who they want to become.