Charles Temple “Charley” Gaynor, 73, of Winchester, VA passed away Wednesday, February 26, 2020, at his home.

Charley was born in 1946 in Elkton, VA, son of the late Joseph and Lavon Gaynor.  He was a graduate of Elkton High School and furthered his education at Virginia Tech earning a Bachelor’s Degree in Marketing Education in 1969. In 1978 he earned a Master’s Degree in Career and Technical Education and completed his degree in School Administration and Education in 1980 from Virginia Tech.

In 1969 he began his teaching career at Clarke County High School and was hired in 1973 to teach marketing classes at John Handley High School.  Charley led the DECA students and the club to win numerous state and national competitions.  He served on several curriculum writing committees for marketing education.  He was the class sponsor of several classes at Handley.  Students and colleagues alike often remarked, “Gaynor, you’ve got to love him!”

Charley was co-manager of Jake and Charlie’s Sports Club Restaurant from 1989 to 1994.

Upon retiring from the Winchester Public Schools in 2002, he was hired on a part-time basis as the Coordinator of Career and Technical Education (CTE).

Charley was very active in key leadership positions in the City of Winchester government which included City Councilor, President of the Council, and at one-point he served as both the President of Council and interim City Manager simultaneously. His terms of service for the City of Winchester government were from 1994 to 2008.

He married his first wife Jane Bergeron in 1967 and they had one son Jim Gaynor. He married his wife Ann Katunas on June 20, 1982 in Winchester, VA, and they had one son Greg. Surviving with his wife Ann are his sons, Jim Gaynor and Greg Gaynor, both of Winchester, VA; his daughter-in-law Laurie Gaynor of Winchester, VA; grandchildren, Megan and Brent Gaynor of Winchester, VA; and Abbie – his canine granddaughter. He was dearly loved by his wife and family.

Charley enjoyed his time at Colonial Beach fishing and boating with friends and family. He was an avid reader of history, enjoyed watching movies, and spending time with his family. Later in his life, you could find Charley on his front porch sipping coffee and talking to the neighborhood community members.

He was a member of Christ Episcopal Church in Winchester. A celebration of life will be held at a later date. In lieu of flowers, donations may be made to the Winchester Education Association for Student Scholarships at https://winchestereducationfoundation.org/ or Handley Judges Athletic Association (JAA) at https://www.judgesathleticassociation.com/.

Arrangements are being handled by Omps Funeral Home, Amherst Chapel.