

Robert, born to the late Harry B. Caldwell, Sr. and Margaret H. Caldwell on October 18, 1940, and was a lifelong resident of Greensboro. He leaves behind three daughters, also of Greensboro: Cathy (Robb) Wells, Janet Caldwell, and Robin (Robby) Eatman. Also surviving him are six grandchildren whom he loved dearly: Margaret Smith (Jacob), Virginia and Alex Wells, and Payne, Mae and Wynn Bradley. He had also recently learned that he was going to be a great grandfather. Also surviving him are brothers and sisters-in-law Ralph (Rita) and David English, Joanne Caldwell and Melinda Wood (Bennett) along with numerous other nieces, nephews and cousins. He was pre-deceased by his lovely wife, Dale, his brother Harry B. Caldwell Jr and parents.
Robert graduated from Greensboro Grimsley Senior High (Class of 1958) and from Wake Forest University (Class of 1962) with a business degree. At Wake, he was a member of Pi Kappa Alpha fraternity and played on the golf team, “bridging the gap between Arnold Palmer and Lanny Watkins.”
After service in the Army National Guard and graduating from Wake Forest, Robert returned to Greensboro where he met Dale English. The two married on December 18, 1965 and celebrated 54 anniversaries together until Dale’s death in 2020.
His love for golf continued throughout his life. He was the Club Champion and Senior Club Champion at Greensboro Country Club on more than one occasion and was a longtime competitive member within the CPGA amateur and associate senior circuits. He regularly competed in the Senior Pro and Super Senior Associate divisions across the Carolinas, carding competitive rounds on historic regional courses.
Robert was a lifelong member of First Baptist Church where he taught Sunday School for most of his adult life, served on numerous committees throughout the church, including serving as Chairman of the Deacons.
Dale and Robert loved to travel throughout the US, having visited all 50 states except North Dakota, and loved visiting spots around the world including Ireland, Denmark, Russia, Germany, Sweden, Italy, England, France, Switzerland, Greece, Turkey, Egypt and on and on. In later years, trips with the entire family became especially meaningful. Of particular note was a memorable trip with the entire family to Jamaica that none of us will forget and a cherished trip to The Homestead, returning to the site of their honeymoon with the entire family, to celebrate their 50th anniversary. Robert especially cherished time spent in Pawleys Island with Dale and his daughters and grandchildren. Robert also traveled extensively in quest of great golf rounds, having played Pebble Beach, St. Andrews and Augusta with many others around the globe.
Robert began working aside his parents at NC Grange Mutual Insurance Company in 1964. In 1980, he was named President of the company a position he would hold until his retirement in 2022. From 1985 to 2003, Robert also served as President of the North Carolina State Grange.
After his retirement, Robert kept busy – driving for Meals on Wheels, having breakfast with other GHS alumni once a month, taking part in ROMEO (Retired Old Men Eating Out) lunches, and playing with “My Buddy,” his dog. Three back surgeries limited his play on the golf course during his last years, but he still loved to watch the tournaments and ride in the golf carts with his friends. He remained a Deacon Club member and avid Wake Forest fan for his whole adult life.
Robert passed away on October 8, 2026, from complications subsequent to a fall. He was cared for by a loving group of caregivers in his last weeks. Special mention is merited for Robertha Goll, who had cared for Dale during her illness and remained a dedicated friend and caregiver to Robert since. The family also thanks Stacey Watkins and Barry Davis for the care they provided.
A memorial service is scheduled for Robert’s birthday, Sunday October 18th at 2 pm at First Baptist Church, Greensboro with a reception following in the FBC Fellowship Hall. The service will be livestreamed on the Church's website: fbcgso.org/memorial/.
In lieu of flowers, the family asks that donations be made to the Homebound Ministry of First Baptist Church (where Dale served as Minister to the Homebound for 21 years) or to Backpack Beginnings.
DONATIONS
BackPack Beginnings3711 Alliance Dr, Greensboro, North Carolina 27407
First Baptist Church1000 W Friendly Avenue, Greensboro, North Carolina 27401
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