Cynthia O'Connor Woolverton

Cynthia Ruth O'Connor Woolverton, lovingly known as Cyn, Grammy, Mama, and Titi, passed away suddenly, leaving behind a legacy of love, laughter, and unwavering support for those around her. Born in Somerset, New Jersey, to Eleanor Cleveland and Anthony Gianchiglia, Cynthia’s life was defined by her deep devotion to family, her sharp wit, and her boundless generosity.

Her daughter, Dr. Katharine “Katie” O’Connor (Aaron Howe), and grandsons, Connor, Callum, and Corban Howe, were the absolute center of her world. She loved them fiercely, celebrated their every achievement, and was their greatest cheerleader in life.

Cyn is survived by her devoted husband, Thomas Woolverton; her daughter Katie O'Connor (Aaron); stepdaughter, Michelle Keller (Jeff); and stepson, Brent Woolverton (Patricia),bonus grandchildren Hunter, Sarah, Kyrsten, Bailey, Tyler, Emily, and Ryan. She was also part of a large and loving family, with many siblings, nieces, and nephews who brought her immense joy throughout her life. She was preceded in death by her mother, Eleanor; father, Anthony; sister, SueAnn; sister, Mary; and brother-in-law, Mack.

For over 30 years, Cyn built a successful career with Walgreens, where she used her leadership to uplift others and give back to the community. Never one to stop learning, she returned to college after retirement, earning her associate degree from FSW and later her bachelor’s degree from FGCU. It was then that she found her true calling—teaching. She embraced her role as an educator with passion, shaping young hearts and minds with wisdom, encouragement, and an unwavering belief in her students' potential.

Beyond her professional and academic achievements, Cyn was a truly brilliant and quick-witted woman who could light up any room with her humor and intelligence. She had an unmatched ability to make people laugh, and her presence brought warmth and joy to those lucky enough to know her. Above all, Cyn had a rare and beautiful gift—she accepted everyone exactly as they were, offering love, kindness, and support without hesitation. She made people feel seen, valued, and cherished. This is how she will always be remembered.

As we grieve her passing, we find comfort in knowing that Cyn now walks in the garden with the One who knows her name, surrounded by peace and love. Though our hearts are heavy, her laughter, wisdom, and unwavering spirit will remain with us always.

Her family and friends will gather to celebrate her extraordinary life, honoring the incredible woman she was and the love she so freely gave. The service will take place on Saturday, March 15th at 10 am at Living Waters Family Worship Center (1315 Viscaya Parkway Cape Coral, 33990), all are welcome to attend. In lieu of flowers, please donate to the grandchildren’s education fund, you may do so here: https://www.529egift.org/FL/KYqkfs.

Rest in peace, Mama. I love you. Your love, laughter, and brilliance will never be forgotten.