Thomas J Cunningham Jr's Obituary
A Tribute to the Life of Thomas “Tom” Jefferson Cunningham Jr.
Thomas “Tom" Jefferson Cunningham Jr. was born on December 16, 1928, in Birmingham, Alabama, to Thomas and Ethel (Hayes) Cunningham. He was the younger brother of Helen, and from an early age, Tom proved to be both resilient and full of spirit. At age seven, facing serious health issues, doctors advised his parents that a change of climate was necessary for him to thrive. The family moved to St. Petersburg, Florida, and there, young Tom found his strength — the beginning of a lifelong love for the city that gave him a second chance.
Tom attended Mirror Lake Junior High and graduated from St. Petersburg High School in 1947. Though he first joined the Naval Reserves, seasickness led him to chart a different course in service, and he joined the United States Air Force, proudly serving for four years. During his military tenure, he was deployed to Okinawa, Japan, in 1952.
That same year, he met Dorothy Shingler while attending a friend’s wedding, and just six months later they married, beginning their 73-year journey of marriage. Dottie was the love of his life. Their bond was an example to all who knew them: rooted in Christ, full of love and devotion and many games of cards.
After leaving the Air Force in 1954, Tom pursued higher education, earning both his bachelor’s and master’s degrees from Florida State University. He became a life time member of the FSU alumni association in 1956. He began his professional career with the South Florida Flood Control District in West Palm Beach. Tom's career path eventually led him to Lanier Business Equipment where he flourished as a top traveling salesman. In 1969, he was transferred back home to St. Petersburg where he and Dottie, and their four boys settled for good. At the age of 52, Tom retired from Lanier, ready for the next chapter.
Retirement for Tom wasn’t about slowing down, it was a time for him and Dottie to pursue their passions. He flipped houses, owned a liquor store (leading to what he and Dottie jokingly called the “biggest fight of their marriage”), and filled his days hunting, fishing, traveling with friends, and playing cards with Dottie. One of the greatest joys of his retirement years was building a house in Highlands, North Carolina, where he and Dottie spent the summers surrounded by nature and cherished friendships. Those Highlands summers became treasured traditions, filled with laughter, porch conversations, and peaceful mountain mornings watching the wildlife.
Together, Tom and Dottie raised four sons: Stephen (Monica), David (Sheree, predeceased), Clay (Sandy), and Brian. He was the proud grandfather to his eight grandchildren: Jason (predeceased), Andy, Bobby, Christina, Julie, Joel, Brittany, and Katie, and their spouses. Tom was also blessed with 14 great-grandchildren to keep him on his toes. Tom loved nothing more than sharing his many life stories, and of course, his endless jokes with his family. Remarkably, he maintained a steady presence in the lives his children, grandchildren, and great grandchildren.
A man of deep faith, Tom was a member of the Methodist Church. He sang in the church choir, worshipped regularly, and led by example in his walk with Christ. He was the spiritual foundation of the Cunningham family. Tom loved the outdoors, the waters of Tampa Bay, dancing, storytelling, and sharing laughs around the dinner table or over a card game. He was known for his quick wit and sense of humor — always ready with a joke or a funny story to elicit a laugh. Even in his final days, he made people smile with his well-timed one-liners and light-hearted charm.
His was a life well lived. He will be dearly missed and forever remembered by those who loved him the most – his family and friends. Tom will be remembered for his deep faith, charm, and most notably, his love for his family (especially Dottie), and the beautiful life they built together.
In lieu of flowers, please make a donation in Thomas's honor to All Children's Hospital.
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