John Williams Boynton Jr

John Williams Boynton, Jr.

John Williams Boynton, Jr., born February 18, 1933, in Baltimore, Maryland, passed away peacefully at the age of 93 on February 19, 2026. He was the son of Dorothy and John "Benny" W. Boynton, Sr.

John was predeceased by his beloved wife of 67 years, Diane Hamilton Boynton, who died in 2021, as well as his siblings, George Boynton (Elsa) and Lynn Randall (Edward).

He is survived by his three sons: John (Jay) Boynton III (Becky), George "Ham" Boynton (Ginger), and Craig Boynton (Rebecca); 9 grandchildren; and 11 great-grandchildren, all of whom were a source of immense pride and joy.

John graduated from The Gilman School in 1950 and from Johns Hopkins University in 1954, where he played varsity lacrosse. He briefly attended the University of Maryland School of Law before serving two years in the United States Army at Fort Bragg.

Education and mentorship became the cornerstones of John's life. He began teaching at The Gilman School before moving to Avon Old Farms School (1956–1961). He later spent 13 impactful years at Greenwich Country Day School, where he taught Latin and coached football, lacrosse, and wrestling. His lacrosse and wrestling teams dominated their conference, as he consistently sought stronger competition to challenge his athletes. Dedicated to scholarship as well as sport, he published two Latin textbooks for use in his classroom.

In 1974, John and Diane moved to New Hampshire, a place they dearly loved. He joined Holderness School, serving as teacher, coach, and Admission Director from 1974 to 1978.

In 1978, John returned to Baltimore and entered the life insurance and pension administration field, founding and running Benefit Designers of Maryland, a third-party administrator specializing in qualified retirement plans. Working closely with agents of the MassMutual Boynton Agency (his brother, George, acting as the General Agent), he designed and administered pension plans for companies throughout the East Coast. He led the company until 1996, eventually bringing his sons Jay and Craig into the business. After turning leadership over to Jay, John returned to his first calling-education-teaching Spanish and assisting with lacrosse at St. Paul's School for Boys.

John was also a longtime counselor at Camp Deerwood, where he was best known as the water-skiing instructor. Camp Deerwood was his true love, and the summers spent there created cherished memories for generations of campers and for John himself.

In 2007, John and Diane moved to Acts Fairhaven in Sykesville, Maryland. There, John remained deeply engaged in community life. He shared his passions for golf and theater by organizing a resident golf program and producing one-act plays performed by fellow residents. He was widely loved for his energy, warmth, and enduring commitment to helping others grow.

John will be remembered as a devoted husband, father, grandfather, teacher, coach, mentor, and friend. His legacy lives on in the countless students, athletes, colleagues, and family members whose lives he shaped with high standards, humor, and unwavering encouragement.

A memorial service will be held at Acts Fairhaven on a date yet to be determined.

Please omit flowers. Contributions, in memory of John Boynton, should be made to the Deerwood Foundation at Attn.: Bruce Wilhelm, 133 Edgewood Road, Cornwall, VT 05753 or can be made online at deerwoodfoundation.org.