George Pope Cawood, Jr.

George Pope Cawood, Jr., age 87, of Middlesboro, KY, passed away on May 22, 2026, at Baptist Health in Lexington, Kentucky. George was born in Middlesboro, Kentucky to Eula Annette (née Graham) and George Pope Cawood, Sr. (“Pope”) on August 22, 1938.

George was inspired in his Christian faith by the example set by his mother and father. He was a lifelong member of Covenant Methodist Church, Middlesboro, KY. As a young boy, George could often be found hanging around his family’s businesses, Cawood Funeral Home and Perry & Pope Drug Store, in downtown Middlesboro. He also cherished time with his Graham grandparents and extended family at the family farm near the Flatwoods community in Lee County, Virginia.

George was a 1956 graduate of Middlesboro High School. He attended Emory and Henry College, Emory, VA, where he earned a Bachelor of Arts in History, and the University of Tennessee, Knoxville, TN, where he earned a Master’s in Education Administration. Despite his academic tenure at UT, George remained loyal to the Kentucky Wildcats throughout his life. 

Upon receiving his degree from UT, George began his career as an educator. His first teaching job was in a one-room schoolhouse at Beans Fork School, Middlesboro, KY, which he fondly remembered as one of his most rewarding experiences. He later taught history at Middlesboro High School, served as the last principal at the old Middlesboro Junior High School before its closing, and became the first principal of Middlesboro Middle School. 

After his years as a school administrator, George embarked on a new career in banking at Middlesboro Federal Bank, Middlesboro, KY, where he worked as a loan officer, followed by Vice-President, and ultimately President of the bank. Throughout his career in banking, he never lost his passion for education. Following his retirement, he joined the Kentucky School Boards Association, where he traveled throughout the state working as a school board team facilitator, training school board members and helping them secure funding for new buildings. George was also elected and served as a school board member for Middlesboro Independent Schools for many years. In addition to his active involvement in the local community, George served his country as a member of the United States Army Reserves.

George had a lifelong appreciation for the American West. He traveled throughout the western United States visiting National and State parks with his family, and with special friends Tim Holt and Patrick Hutchens.

In addition to his parents, George was preceded in death by his grandparents, James Frank and Mary Victoria (nee Pope) Cawood of Cawood, Kentucky and William and Emma (née Hobbs) Graham of Lee County, Virginia; mother and father-in-law, William Edward and Martha Frances (née Miller) Wilson; sister-in-law Addie Lou Cawood, and nephew Mark Wilson.

George is survived by his wife of 58 years, Patricia (nee Wilson) Cawood; daughter, Elisa Anne Cawood; granddaughter, Catherine Olivia Zanca; brother, Hobart G. Cawood; brother-in-law, David Wilson (Debra Walter); nephews, Stephen (Kassi) Cawood and Brian Wilson; niece, Toni (Mark) Butterfield; and cousin, Paul Connor (Laura) Cawood as well as many other relatives and close friends.

The family of George Pope Cawood, Jr. will receive friends on Friday, May 29, 2026, from 5:00 p.m. until 7:00 p.m. at the Cawood Funeral Home Chapel, Middlesboro, KY. Funeral services will immediately follow at 7:00 p.m. with Reverend Chuck Shroll presiding. Music will be provided by Nicole Mike. 

On Saturday, May 30, 2026, family and friends will meet at Cawood Funeral Home, Middlesboro, KY, at 11:00 a.m. to travel in procession to Green Hills Memorial Gardens, Middlesboro, KY, where graveside services will be held. 

Pallbearers will be Paul Connor Cawood, Jr., William Edward Cawood, Dr. Stephen A. Cawood, William Jospeph Holder, Jr., Stephen C. Cawood, and Christopher Jacob Partin, Sr. 

In lieu of flowers, the family requests that memorial gifts be made to Covenant Methodist Church, 602 Dorchester Ave., Middlesboro, KY 40965.

Online register book and condolences are available at www.cawoodfh.com.

All arrangements for George Pope Cawood, Jr. are under the care of Cawood Funeral Home, Middlesboro, KY.