History of Bray & Oakley
Our Agency was originally founded in 1920 as Claypool & McGuire Insurance Agency with John Claypool and John McGuire as the operators. Additional incorporators of that original agency were Harold H. Oakley and Lilly McDonald Oakley.
In the middle of the 1920’s Robert M. August acquired the agency and hired A.B.C. Bray, Jr. They later became partners and formed August & Bray Insurance Agency.
Meanwhile, the H.H. Oakley Agency was formed in 1935 by our original incorporator Harold H. Oakley. He then brought in his son Frank H. Oakley, who later was very instrumental in merging our present-day Bray & Oakley.
After Robert August passed away, the Claypool & McGuire Insurance Agency continued under Albert Bray and Robert L. Copley’s leadership. In 1961, Albert Bray of the August & Bray Insurance Agency merged with Frank H. Oakley of the H.H. Oakley Insurance Agency and became Bray & Oakley Insurance Agency, Inc.
Albert Bray retired as the president in 1979. Frank H. Oakley then became president, and Clinton Winter vice president.
In 2002, Frank H. Oakley retired, and Clinton Winter became president. In 1999, Clinton Winter brought in his son, Michael P. Winter, who is the vice president.
The agency has continued to grow and prosper and add branch offices, with the first being in Lexington, KY in 2014, followed by Pikeville, KY in 2016, Richmond, KY in 2017, and Chapmanville, WV in 2019.
