Cyrus Benson Jr. Obituary

Cyrus Benson Jr.

Who was Cy Benson? A loving husband to Miriam; a devoted dad to Cy, Tom, Bob, and Bill; a lifelong educator and coach; and a man who brought warmth and compassion to every encounter.

Cy was born in Brooklyn, N.Y., the only son of Cyrus and Ellen Benson, and died at home on Feb. 19, 2023, after a brief illness. In between those two events, there was lots of living and loving.

Cy’s life and passions are defined by consistent themes: family, education/coaching, and relationships.

He was a gifted athlete, beginning at an early age in Babe Ruth baseball (coached by his future father-in-law William C. Fitts, Jr.), but football was the sport that dominated - threading through his 87 years. His last trip was to UPenn to cheer on the Quakers football team, which his son Bob coaches.

Cy grew up in Mamaroneck, N.Y., and graduated from F.E. Bellows High School in 1953, where he exhibited strong leadership skills and excelled (and focused) more on the football field than the classroom. He attended Cornell University in Ithaca, N.Y., where he played Ivy League basketball and football and forged life-long friendships. He graduated in 1957 with a BA and worked briefly in corporate America as a sales representative for IBM. His career was interrupted by a call to serve in the United States Air Force as an Instructor Navigator for two years of active service. He was honorably discharged from the reserve in 1970.

During his active service in the Air Force, Cy took an important leave to return to Mamaroneck in the summer of 1960 to marry Miriam Fitts, with whom he treasured 62 years of married partnership.

In 1962, Cy earned his master’s in education from Springfield College in Massachusetts and launched his life-long teaching/coaching career at Monmouth Regional High School in New Jersey. His career success brought him and his quickly growing family to Vermont’s Northeast Kingdom in 1970. Buying an old, fixer-upper farmhouse on a hill in Morgan, Vt., Cy built his life around his family (now four sons and Miriam) and the community where he lived and worked. He integrated his love of sports and teamwork into a value system and lifestyle that respected everyone - students, colleagues, neighbors, friends and extended family. Like all successful competitors, he wanted to win, but not at any cost. More important to him were integrity, hard work, collaboration, and a can-do attitude. He greeted and acknowledged everyone he met - and made them feel seen and understood. He had charisma, for certain. It may sound like a cliche, but folks literally “lit up” when Cy walked in a room, restaurant, or store. He made friends with everyone. Valuing consistency and loyalty, he found change difficult and at times was seen as stubborn and inflexible.

Career-wise, he progressed from coach and classroom teacher to administrator: for more than 10 years at North Country Union High School in Newport, Vt., in various supervisory roles; for six years as Headmaster at Lyndon Institute in Lyndon, Vt.; and then returning to North Country Union H.S. for five years as Co-op Education Coordinator, Adult Services Administrator and coaching the football team to a state championship! In 1994, Cy worked for the Vermont Department of Corrections as a Reparative Board Facilitator, still focused on helping young people by offering alternative sentencing to first time offenders. He continued his involvement in education until his retirement in 1988.

During his long career, Cy received many accolades and honors, including Lyndonville, VT Citizen of the Year in 1987 and Administrator of the Year in 1988.

Life-wise, Cy and Miriam focused on raising their four active and gifted sons, who excelled in sports and academics, each with unique talents and personalities. Cy was predeceased by his granddaughter Hope Alexander Benson and his son Thomas Fitts Benson. He is survived by Cy and Jessica Benson, Bob and Juli Benson, and Bill and Nancy Benson. In addition, he leaves his beloved grandchildren: Nicholas, Connor, Kaylyn, Luke, and Liam.

The family is appreciative of the kindness and concern shown by Cy’s many friends. In lieu of other memorial gifts, please send donations to BAYADA Hospice, 316 Main Street, Unit EH-6, Norwich, VT 05055.

Condolences may be left to Cy’s family at an online guestbook at

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