Obituary: John D. Bailey, Sr.

“There are few men left standing who gave so freely of themselves to ensure that my hometown could continue to offer the best in cultural, educational, medical, recreational and financial opportunities as John Bailey.  He will always remain in my memory as a man of character and a model of good citizenship for our future.”  Michael Gold, Editor, Historic City News.

The flags at City Hall will fly at half-staff on August 28, 2018 as is the custom upon the death of former mayors and recipients of the de Aviles Award or the Order of La Florida.

“The elected officials and entire staff of the City of St. Augustine join the community in sending our condolences to the family of John D. Bailey Sr. who died last Friday, August 17.  As an elected official, he served St. Augustine during some pivotal times. He was elected to the City Commission in 1963 and became Mayor just two years later presiding over the city’s 400th anniversary in 1965.  Mr. Bailey’s influence in St. Augustine stretches far beyond his public service in government. He cared for our community through his service on the boards of many charitable organizations and on those of businesses important to the community’s livelihood.  In 1977, Mr. Bailey was honored by the city with the Order of La Florida, being the third person to receive the city’s highest award.”  John Regan, St. Augustine City Manager.


John Denver Bailey, Sr., passed away peacefully at home surrounded by family and loved ones on August 17, 2018, at the age of 94. John was born May 10, 1924, in Hartwell, Georgia to parents Denver and Jewell Bailey. Denver, a Georgia Power foreman, and Jewell moved John and his younger sister, Frances, to Athens in 1937, thus beginning John’s love affair with the University of Georgia Bulldogs. John Denver, as he was known in Athens, frequently rode his bike to the stadium to watch the Dawgs practice and listen to the Redcoat Band. After graduating from Athens High School, John enrolled in the University of Georgia to pursue a degree in Business and was active in his Sigma Chi fraternity. However, the start of WW II interrupted his education. Eager to defend his country, he enlisted in the United States Air Force in April of 1943. He was a member of the 234th Army Air Forces Base Unit and participated in the battles and campaign air offensive against Japan as a B29 Aerial Gunner. John was honorably discharged in February of 1946. After his military service, John returned to Athens to complete his college education. On his first day back on campus and looking forward to playing the field, he was swept off his feet at a dance when he admired the lovely shoulders of Margaret “Peggy” Bassing, who became the love of his life. They celebrated their 70th wedding anniversary in June of this year.

John graduated from the University of Georgia in 1947 with a business degree and joined the Insurance Company of North America. After completing his training in Philadelphia, he moved to Orlando to work as INA’s agent liaison for the State of Florida. Shortly thereafter, he and Peg married in Augusta, Georgia on June 25, 1948. They lived happily in the Winter Park area of Orlando for seven years, welcoming the first two of their five children. John and Peggy moved to St. Augustine in 1954,where he became a partner in the Thompson-Ryman Realty Company, which was subsequently renamed the Thompson-Bailey Agency and later became the Thompson Bailey Baker Insurance Agency. In 1996, John joined his son, Mark, at The Bailey Group, enjoying the title of Founding Executive and Director of Morale. There he enjoyed holding court in his office, giving free advice and serving as a friend and confidant to employees and clients. He was an astute businessman and continued to monitor his business activities well into his 80’s.

A Memorial Mass will be held at 11:00 a.m. on August 28, 2018, at the Cathedral Basilica – St. Augustine. In lieu of flowers, memorial donations may be made to, Bailey Family Center for Caring, 4266 Sunbeam Road, Jacksonville, FL 32257; Flagler College, John and Peggy Bailey Scholarship Fund, P O Box 1027, St. Augustine, FL 32085-1027; Lightner Museum, 75 King Street, St. Augustine, FL 32084; or your favorite charity. The family would be honored if you choose to wear black and red in recognition of Big John’s love for the University of Georgia. Craig Funeral Home and Crematory Memorial Park is in charge of arrangements.

The move to St. Augustine was the beginning of the happiest years of their lives. John enjoyed a successful career in the insurance and real estate industry. Along with that success came a heartfelt desire to give back to the community. John dove in headfirst, serving on numerous boards, representing the City as a Commissioner from 1963 to 1967 and serving as Mayor from 1965-1967 during the city’s 400th Anniversary. He was most proud of his relationship with Flagler College and the success it has achieved, having joined its board of trustees in 1971 and serving for over 40 years before recently being named Trustee Emeritus. He was also very proud of serving on the Lightner Museum board of trustees for 30 years, Florida School for the Deaf and Blind Foundation board, Flagler Hospital board through the 1960’s and 1970’s, Barnett Bank’s board of directors for 28 years, Historic Preservation Board, Kiwanis Club, YMCA and the St. Johns County United Way. John received recognition over the years for his achievements and community service. He was honored by the City of St. Augustine as recipient of the “Order of La Florida”, honored by the Salvation Army as recipient of the Gus Craig Award, recognized by the St. Johns County Welfare Federation as its Community Volunteer of the Year, and named Jaycee Young Man of the Year. While John was busy with his career and community service, Peggy was holding down the home front, serving as a gracious hostess and partner to John and being the mother to a now- busy household of five. John and Peggy enjoyed wonderful, warm, lifelong friendships and watched St. Augustine transform from a small, quiet town in the 1950’s to the bustling tourist destination it has become today. John was an unofficial tour guide for St. Augustine, often taking visiting friends and clients on three hour tours of the city that always included Flagler College and the Lightner Museum. He and Peggy were fortunate to have a waterfront view of the city and he always said that you could go all over the world and never see any place more beautiful than St. Augustine.

John never met a stranger and had friends from all walks of life. As a member of the Greatest Generation, he was fiercely patriotic and proudly wore his flag pen on his jacket lapel. John loved the Georgia Bulldogs, boiled peanuts and an occasional Early Times. If you wanted to make him happy, a skillet of cornbread and buttermilk always did the trick. Most importantly, he loved people. He sought out any opportunity to go out to dinner, host a great party and, in general, just get people together. He taught that a good handshake told you a lot about people and would make a point of instructing those who might not know the art of the handshake. The annual GA/FL game was one of his favorite weekends and his party bus to the game is a memory that many will never forget. He lived life to the fullest and enjoyed helping others do the same.

Despite his many business, social and community endeavors, his family remained his pride and joy. He was great at giving advice to his children and grandchildren and did not mind letting you know what you should have done differently. Although the last several years have been difficult for him, there was not a moment of complaint or any utterance that he would rather not be around. On his 94th birthday when asked what he wanted the most he replied, “I want to be around a little longer”. John Bailey lived an extraordinary life filled with friends, family and lots of love. To say that he will be missed is an understatement.

He is survived by his wife of 70 years, Peggy, children, John D. Bailey, Jr ,Bruce Carlton Bailey, Joanie Bailey Thornton (Tom), Mark Franklin Bailey, Sr. (Alecia), all of St. Augustine, and Cathy Bailey Peterson (Bob) of Atlanta, Georgia. He was extremely proud of his twelve grandchildren and 19 great-grandchildren. He was pre-deceased by his parents, Denver and Jewell Bailey and his sister, Frances “Freddie” Sims.

The family would like to extend their heartfelt thanks to Community Hospice and John’s personal caregivers (Chris, Cathy and Bobbie) for the excellent and loving care that John received over the last several months.

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