History of Bray & Oakley

Agency’s Founding in 1920

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.

August & Bray Insurance Agency Forms

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.

H.H. Oakley Agency forms

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.

Albert Bray of the Claypool & McGuire Insurance Agency Merges with Frank H. 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 Retires and Clinton Winter Became Vice President.

Albert Bray retired as the president in 1979. Frank H. Oakley then became president, and Clinton Winter vice president.

Frank H. Oakley Retires and Clinton Winter Becomes 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.

Continues Growth

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.

Contact Bray & Oakley Insurance Agency Today!

Don’t wait! Get in touch with an office near you and talk with one of the best insurance agencies around. Our staff will see to your needs and talk things through with you. Stop dealing with automation and cold sales and start dealing with people again.