AUGUSTA, Ga. — We celebrate the life of Heyward Holson Bailey, 92, family pillar and community leader who entered peacefully to rest on Tuesday, March 10, 2020. Married for 62 years to his beautiful wife, Mary, who passed in 2015, Heyward was widely known for his passions: caring for people; horses and everything about them; hospitality; décor and design; serving God; and everything Southern. 

Born in Modoc, S.C., on June 30, 1927, Heyward was an animal lover from early in life. He raised and trained homing pigeons as a boy and maintained a lifelong love for birds. In his teen years, he became an avid English hunter-jumper rider, and was known for teaching horsemanship to generations of riders around the CSRA and up the East Coast. Talented in many aspects of horse sports, Heyward enjoyed fox hunting, playing polo and dressage riding. Among the many horse associations in which he was active, he was an ardent member of the James River Hunt Club in Hampton  and was among the only surviving members of the Augusta Polo Club (c. early 1940s). Heyward’s skill in the jumping ring continued to win him show ribbons well into his 80s. 

Heyward was known as a hard worker in all that he did. With honors in ROTC, Heyward graduated from Augusta’s Richmond Academy in 1944 and served in the Army Signal Corps in World War II at Fort Belvoir in the Washington, D.C. area. Working early in his life on his customer service skills, Heyward was an ice cream scooper at the local soda shoppe, worked at the Augusta employment office finding jobs for the unemployed and then at the Augusta Cotton Exchange as a staff accountant. In his 20s, he was hired on by J. C. Penney Co. and was a “Penney Man” through-and-through, embracing the company’s original purpose as the Golden Rule Store, and training personally with Mr. James Cash Penney himself. Heyward rose through the management ranks easily, with positions in Augusta and Savannah, Georgia, Jackson, Miss., Knoxville, Tenn., Oklahoma City, Okla. and Anderson, S.C. where in 1969 he opened the first Penney store in an indoor shopping mall in the region. There he became mall President and an advocate for retail marketing and public relations. 

Bailey’s business successes led to his appointment as the store manager to open the Hampton Penneys in 1973, where he quickly grew the store into the highest grossing J. C. Penneys in the chain. He became president of the Coliseum Mall and worked in leadership on the Peninsula Chamber board in Virginia. He became well-known in Southeast retail for his community relations and his press events with celebrities, notably those in the Miss USA pageants and regional and national sports events, enjoying camaraderie with tennis pros in the 1970s. Known as “Mr. Bailey” to thousands of employees over his career, Heyward became a teacher in retail and business management, continuing his long tradition of taking young business students under his wing, and he began mentoring youth through DECA and Junior Achievement in Virginia public schools. 

Recognized nationally for his talents in networking, benchmarking in advocacy for retail management, and volunteerism, Heyward was tapped by the National Retail Merchants Association for state, regional and national awards of Excellence. A strong Rotarian, serving Rotary Club International in several states, he hosted international business leaders and helped create the global business network that Rotary has become today. 

Bailey built and enjoyed his dream home in Carrollton with a small private stable for his horses on the James River. Upon retirement from retail management in 1987, Heyward brought his bride back to Augusta to be near family. He replanted himself into his Georgia community once again and served in finance, administration and benevolence with First Baptist Church of Augusta, with a special love for his work with The Augusta Habitat for Humanity. Always devoted to serving God and people through his church, Heyward served as a Sunday school teacher and a deacon in the Southern Baptist Church throughout his life. 

He commenced a second career with Westover Memorial Park in sales and counseling those in bereavement. Always active and friendly with his neighbors, Heyward served on his neighborhood boards, including those of Willow Creek in Augusta and Amberley at Riverwood Plantation in Evans. 

As the strong patriarch of the Bailey family, Heyward’s family will greatly miss his fearless guidance, enormous heart and fun-loving nature. Surviving him are his children whom he treasured, Elizabeth Bailey Hodges of Evans, Ga. and Newport News, and Lydia Bailey Brown (Michael) of Evans, Ga. and Louisville, Ky.; and his grandchildren, whom he adored and admired; Michael Cary Brown, II (Sarah) of Myrtle Beach, S.C.; Callie Page Brown of Dyer, Ind.; and Tyler Harriss Hodges of Hampton. Too, he is survived by four generations of beloved nieces, nephews and cousins. His passing was preceded by his wife, Mary Harriss Whitaker Bailey; his parents, Henry W. Bailey and Willie Ethel Holson; his brother, Henry Ellison Bailey; and his sisters, Martha Bailey Moore and Willie Vivian Bailey. Because of his impact on others as a helper and leader, and due to his genuine kindness, Heyward H. Bailey will be remembered by more friends than most people would ever dream of even meeting, and by thousands of former employees and horseback riding students whose lives he touched for the better. 

Family received friends March 15 at Thomas Poteet & Sons Funeral Directors, 214 Davis Road, Augusta. A graveside service was held March 16 at Westover Memorial Park, 2601 Wheeler Rd, Augusta, with celebration and memory-sharing afterwards at the First Baptist Church’s Storey Chapel and Fellowship Hall, 3500 Walton Way Extension, Augusta. 

Thomas Poteet & Son Funeral Directors, 214 Davis Road, Augusta GA 30907, 706-364-8484, is assisting the family. 

Please sign the guest book at www.thomaspoteet.com