In the early 1980s, Barbara Ann Clay was managing a restaurant in Greenport when an opportunity arose for a potentially life-altering move. She was in her 20s and had been offered a chance to intern at the White House under David Stockman, then director of the Office of Management and Budget.
As she considered the move, she consulted her parents and one other man — Richard Hilary, her former principal at Southold High School, where she graduated from in 1972.
Mr. Hilary had already helped instill a sense of self-confidence in Ms. Clay, who felt ostracized at times growing up due to her weight.
“He told me countless times: ‘You can go and do it. Whatever it is,’ ” Ms. Clay said.
Mr. Hilary’s advice to her in that moment helped shape her life: “Don’t be limited by what you see around you,” Ms. Clay recalled him saying.
A revered administrator, teacher and coach who influenced generations of students in his various educational roles and who was an avid outdoorsman committed to conservation, Mr. Hilary died Nov. 13 in Cooperstown. He was 79.
Mr. Hilary spent close to 30 years in Southold schools, with the bulk of his time in the 1970s and 1980s as principal at both the high school and middle school and as an interim superintendent. He continued working well after his retirement as an educator in Southold, most notably as director of the Peconic Dunes Camp, which is part of Cornell Cooperative Extension.
“He was a workaholic,” said his son Scott Hilary of Southold. “He was always busy with a lot of creative, innovative initiatives, mostly to do with conservation and education.”
A native of Sidney, N.Y., Mr. Hilary graduated from SUNY/Cortland, where he played football. He developed a love for the outdoors by fishing and hunting as a kid in the Unadilla and Susquehanna River Valley. He became a Boy Scout and achieved the highest rank of Eagle Scout. Scouting remained a big part of his life in later years, when he served as a longtime scoutmaster of Southold Troop 6. He continued his conservation and environmental initiatives upstate after retiring in the area where he grew up.
His two sons, Scott and Richard (Chip), both achieved the Eagle Scout rank under their father’s guidance.
Scott said the core values of scouting were a fundamental part of how he and his siblings were raised.
Jim McMahon, the former director of Southold Town’s department of public works, met Mr. Hilary when both their sons were involved in the Boy Scouts and would often work alongside him on various Eagle Scout projects.
“His connection with being at the Southold school and how dedicated he was to the Boy Scout program really drove a lot of young scouts into the program,” he said.
Mr. Hilary was instrumental in the success of the Peconic Dunes Camp, Mr. McMahon said. A former teacher himself, Mr. McMahon said he was always impressed to see how Mr. Hilary impacted kids’ lives and could get them excited about the environment.
“His enthusiasm, his ability to get kids involved really made a big difference in the kids that were involved in the program,” he said.
Mr. Hilary was principal when all three of his children came up through school. He was the middle school principal during Scott’s time and the high school principal when Chip and his daughter, Holly, graduated.
Mr. Hilary was instrumental in the start of the NJROTC program in Southold during the 1970s. At the time, Southold was the first school in the state to have a program, according to Major William Grigonis, who graduated from Southold the same year as Mr. Hilary’s daughter. Maj. Grigonis now runs the NJROTC program.
“For me, he was also a family friend,” Maj. Grigonis said, fighting back tears. “I got to know them very close.”
He remembered Mr. Hilary as someone who always pushed students to be their best and helped transform the school into one big family. He was a larger-than-life figure who commanded respect, and kids at the time knew to be on their best behavior when Mr. Hilary was around.
Even outside of school, Mr. Hilary’s presence was constant. He could often be spotted driving an old, blue station wagon with yellow lettering on the side signifying the Southold School District.
“He would honk, he would wave and if you looked like you were doing something wrong he would point his figure at you as he drove by,” Maj. Grigonis said. “You didn’t want to do something wrong, because old Mr. Hilary would get you.”
Judi Fouchet, who graduated from Southold in 1980 and is currently vice president of the Board of Education, keeps in contact with several classmates through a group chat. When the word spread of Mr. Hilary’s passing, the group members had all positive memories, she said.
“The sentiments were he was a good guy and he was fair,” she said.
A memorial service was held Nov. 18 at C.H. Landers Funeral Chapel in Sidney. He was predeceased by his parents, Bea and Francis, his wife, Evelyn, and a brother, Melville (Skip). He is survived by his children, Holly Hilary Moreno, Richard (Chip) Hilary, and Scott Hilary as well as his grandchildren, Elizabeth, Ashley and Cole, and a great-grandson, Quinn.
His family plans to hold a celebration of his life on June 3, 2018, at Founders Landing (The Wharf House). A scholarship fund for Southold students will also be established in his memory, his son Scott said. Scholarship donations will be welcomed at the celebration.
For more information on the scholarship fund or the celebration, contact Scott Hilary at [email protected].
Reflecting back on her career, Ms. Clay attributes much of her success in politics and international affairs to the faith her principal showed in her as a youth. He encouraged her to take chances in life and to never settle.
She recalled the time after high school when she considered attending school in Switzerland to gain an international experience. She had her doubts — how to pay for it for starters. And there was the boy who worked at the restaurant she was interested in and didn’t want to leave.
She consulted Mr. Hilary, who with “his inimitable subtlety,” made clear what she should do.
“Can’t remember that boy’s name,” she said all these years later.