Robert passed away at St. Francis Hospital on March 4, 2025. He was born in Duck Hill, Mississippi on November 10, 1935 to Gertrude and Pat McCaskill. His family moved to Memphis in 1940 where his father was an engineer on the City of New Orleans train. He attended A.B. Hill Elementary School, graduated from South Side High School and Memphis State. He was very proud of having grown up in South Memphis and remained close to many of his high school friends. He became a Professional engineer, started his own firm, which was very successful and worked there until his retirement in 2018. He was well known and respected in the construction and development community. He designed buildings for Kemmons Wilson, the founder of Holiday Inns, and Kemmons referred to him as the "worlds greatest engineer". In the 1980's he was involved with Henry Turley in the re-development of downtown and Beale Street. He structurally designed hundreds of hotels around the world as well as warehouse and office buildings.

He loved riding his horses and was thrown over the heads of most of them. He was a proud member of Hernando Baptist Church where he taught Sunday School for 40 years. He was preceded in death by his daughter Lauren Scarborough and is survived by his high school sweetheart and wife of 70 years Ann Bailey McCaskill, a son Tim McCaskill (Teresa), four grandchildren Wendy Scarborough Remmers (Joe), Matthew Scarborough, Caitlin McCaskill Burke (Austin), Connor McCaskill (Charley) and seven great grandchildren. The funeral will be held Tuesday, March 11, 2025 at 2:00 pm at Forest Hill Cemetery East with visitation beginning at 1:00 pm.