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Hill Community Mourns the Loss of Revered Longtime Faculty Member and Coach Dick O'Shaughnessy '50

We have learned the sad news that one of Hill’s greatest treasures, Richard E. "Dick" O’Shaughnessy ’50 P’73 ’76 ’80 GP ‘05 ’10 ’13, a member of The Hill faculty from 1959 – 1996 and father of Senior Master of the Arts Ellen O. Nelson P’10 ’13, passed away on December 5 at the age of 89.

To begin to get a sense of who Dick was and the impact he had on generations of Hill students, one needs to look no further than the 1994 Dial, which was dedicated to Dick.  The four-page dedication begins, “Sometimes the best leaders in a community are the silent ones, the sages that lead by example.  Mr. Richard E. O’Shaughnessy is just such a person.  Since his post-graduate year, Mr. O has brought to this community a zesty love of life that few, if any, can match.”  He was widely regarded as a soft-spoken, extraordinarily kind, compassionate, and principled man; one who was tough but fair and who made each person with whom he interacted feel that he cared deeply about them and their success.  

The O’Shaughnessy connection to The Hill began in the fall of 1949 when Dick arrived at the School for a post-graduate year.  He was a standout lineman and linebacker on Hill’s undefeated 1949 football team and he starred on the 1949-50 wrestling team, winning his weight class at the National Prep tournament as he helped lead Hill to the second of 11-consecutive National Prep championships.  Dick also was a member of the undefeated 1950 spring track and field team.

After graduating from The Hill, Dick attended the University of Michigan, where he continued his stellar football and wrestling careers.  Dick was captain of Michigan’s 1953 football team, and on the wrestling mat he was a two-time Big-10 champion. 

While at Michigan, Dick caught the eye of Winifred “Winnie” Sarr, whom he married in 1954, beginning a 66-year marriage.  

In 1959, Dick returned to The Hill as an instructor of science and instructor of physical education following an honorable discharge from the U.S. Air Force, where he was an electronics warfare officer.  In his first year at Hill, Dick was the director of Hill’s first Hill Christian Association summer camp, and in 1962 he became the supervisor of camp activities for The Hill Summer Camp in Wolfeboro, N.H., a capacity which he held for nine summers.  

Dick was appointed head football coach in 1964, succeeding the legendary Frank Bissell ’33, who remained an assistant coach on the football staff while Dick assisted him on the wrestling squad. 

The Lawrenceville game in Dick’s second year as head coach has become enshrined in Hill School lore.

On a dreary November afternoon, a Hill team sporting a record of three wins and four losses traveled to New Jersey to meet an undefeated Lawrenceville team.  Hill entered the fourth quarter with a 12-7 lead, but quickly surrendered two touchdowns and suddenly trailed 19-12.  With six minutes remaining, Hill forced a Lawrenceville punt and took possession needing to cover most of the field.  Knowing his first string was low on energy, Dick began platooning groups on an every-other-play basis: while one group was on the field, the other was on the sideline catching its breath and reviewing the next play.  His strategy allowed Hill to move the ball effectively downfield while running time off the clock, and with 20 seconds remaining Roger Waltemyer ’66 scored to pull Hill within a point. 

It was time for Dick, or “Coach O” as he was known to his players, to make one final decision.  A relatively new rule at the time allowed a team to attempt a two-point conversion following a touchdown.  Rather than attempting to kick an extra point, Coach O took the ultimate gamble and elected to attempt a two-point conversion.  He called Waltemyer’s number again, and Waltemyer stormed up the middle, only to be met by a swarm of Lawrenceville defenders who stopped him short of the goal line.  Except, as Headmaster emeritus David Dougherty would emphatically state in his annual Lawrenceville Weekend Chapel talk, he didn’t have the ball.  The ball was in the hands of Chip Piper ’66, who scampered into the endzone untouched to lift Hill to the 20-19 victory. 

Dick remained head football coach through the 1983 season.  His final team was one of his best, winning the final five games of the season to finish the year with a 6-2 record.  Following a 24-14 victory over Lawrenceville, the members of the victorious Hill team hoisted Dick onto their shoulders and carried him off the field.  An excerpt from the football team page in the 1984 Dial reads, “As any member will attest, Mr. O’Shaughnessy gave himself to the team during every moment of the season. This included the brutal pre-season practices as well as the lavish dinners that he and his equally caring wife provided every Friday evening. He was a friend on and off the field, gladly giving advice and comfort at any time.”

Although he was ready to step out of the head coaching role in 1984, Dick couldn’t step away from the gridiron altogether.  He coached at the sub-varsity level for three years before returning to the varsity staff as an assistant in 1987.  Throughout his time at Hill, Dick also was an assistant coach in the wrestling and track programs.     

In addition to serving as an instructor of science and as an instructor of physical education, Dick was the assistant dean of students from 1974 – 1978 and the dean of students from 1978 – 1986.  He oversaw the Dining Hall captains for several years and, as is natural for any longtime boarding school employee, he served on countless committees throughout his 37-year tenure. 

If any faculty family best personifies the family boarding school idea, it would be the O’Shaughnessys.  Dick and Winnie raised seven children on campus: sons, Timothy ’73, Patrick ’76, and Andrew ’80; and daughters, Susan, Ellen, Mary, and Ann.  In addition to Dick’s 37-year tenure on the faculty, Winnie worked at Hill for 26 years, making history in 1970 by becoming the first woman appointed to Hill’s faculty.  Initially hired as an instructor of reading, Winnie later became chair of the Academic Support Services Department, and in 1987 she became the director of testing, helping students navigate the standardized testing aspect of the college application process.  That same year, Ellen joined Hill’s Arts Department and spent the next decade working alongside her parents. 

In 1970, Dick and Winnie purchased and renovated a 200-year-old farmhouse and barn near Wolfeboro in Mirror Lake, N.H., which became the family’s summer retreat, and later their home.  Dick converted the barn into a blacksmith shop, The Country Forge, which he operated as a summer job from 1974 until his retirement from Hill, when he became a fulltime blacksmith.  He and Winnie also became avid fly fishermen and spent ample time enjoying the outdoors.  

The Hill remained an important part of Dick’s life following his retirement.  He often returned to campus and several times he provided motivational talks for the football team prior to the Lawrenceville game.  When the Athletics Hall of Fame was established in 2012, Dick was one of 17 members elected to the Founders Hall, a one-time induction class of the “uncontestable legends of Hill’s athletics history.”

Dick is survived by Winnie; their seven children; and several grandchildren, including Brooke Warren ’05, Marie Nelson ’10, and Tom Nelson ’13.  Plans for an on-campus remembrance of Dick will be communicated at a later date.  

In lieu of flowers, please send memorial donations to The Hill School at the address below or online to support financial aid in honor of Dick O'Shaughnessy.

Those alumni and friends wishing to send expressions of sympathy may send them via email to dwosh@yahoo.com.