Larry Henry Cheek, 85, of Taylorsville, died peacefully at home Sunday, Feb. 15, 2026.
He was born in Spencer County. He was the son of Howard Hillary and Mary Elizabeth Brookshire Cheek. He was a lifelong resident of Spencer County, and he graduated from Taylorsville High School in 1958. He was a devoted member of First Baptist Church of Taylorsville.
He earned his undergraduate degree from Western Kentucky University in 1962, followed by his master’s degree in 1965 and his Rank 1 in school administration in 1970. He began his career with Spencer County Schools as a teacher and assistant coach before becoming head coach, proudly leading his teams to an impressive 85–29 record.
While teaching, he also worked for two years as a Farm Bureau agent. In 1970, he became principal of Bloomfield Middle School and later Eli Brown Elementary School, where he completed his distinguished career in education. He retired after 34 years of dedicated service.
He was an active member of the Nelson County Education Association, the Kentucky Association of Secondary School Principals, the National Association of Secondary School Principals, and the Kentucky Association of Secondary School Administrators. He was honored as Kentucky Principal of the Year in 1993. He served on the board of directors for the Kentucky Association of Secondary School Principals for 23 years and continued representing retired principals following his retirement in 1996.
Beyond education, he was what many would call a serial entrepreneur. He served on the board of directors for The Peoples Bank from 1994 to 2020, and on the Spencer County Board of Health from 1998 to 2021. He was a lifelong farmer, tobacco surveyor, avid golfer, antique collector, business partner in grocery stores, shared ownership of the Hampton Inn in Richmond, and was a proud Kentucky Colonel. He was a devoted Kentucky Wildcats and Western Kentucky Hilltoppers fan, and he especially enjoyed tailgating for football games.
He cherished daily coffee time with his buddies, DL Chowning, Donnie Roberts, and Dale Simpson. His greatest pride and joy were his children and grandchildren. He dearly loved his cats, Amy and Kiki, and held fond memories of friendships formed in high school, at Western Kentucky University, and during his years at Old Kentucky Home Country Club.
He is survived by his beloved wife, Anna Ruth Cheek; one daughter, Lori Ann Cheek; one son, Brian Keith Cheek (Janie); two brothers, Francis Warren Cheek (Donna) and Ronald Wood Cheek (Lora); and his treasured grandchildren, Jonathan Isaac Cheek, Sophia Jane Cheek and Anna Gentry Cheek.
The funeral was Wednesday, Feb. 18, 2026, at the Greenwell-Houghlin Funeral Home in Taylorsville with Pastor Chance McConnell officiating. Burial was in Highland Memory Gardens.
The family requests that expressions of sympathy take the form of contributions to Taylorsville First Baptist Church.
The Greenwell-Houghlin Funeral Home is in charge of arrangements.
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