With heavy hearts and deep love, we share that Diane (Poole) Hennessy, 64, passed away peacefully at home on September 12, 2025, surrounded by the love of her family.
Diane was born on January 11, 1961, in Brockton, Massachusetts, to the late Charles W. Poole Sr. and the late Dorothy (Sylvia) Poole. From an early age, she was known for her creativity, strength, humor, generosity, and playfulness-qualities that only deepened with time. She was the life of any party and probably the planner of it too. She truly knew how to enjoy life to the fullest and make time to stop and smell the roses. She lived a life filled with love, laughter, and devotion to those she held dear.
She will be remembered most for her selflessness, warm smile, volunteer work, her gentleness and way of caring for others, her crocheted gifts, her love of being in Martha’s Vineyard, and most of all- her time spent with those she held close to her heart, especially her grandkids. To those who knew her, Diane’s presence was a gift, and her legacy will continue in the countless lives she touched.
Diane’s greatest treasures in life were her husband of 39 years, Lawrence Hennessy; her daughter, Brittney Hennessy; her stepson, Christopher Hennessy, and his wife, Natalie; her niece, Ronda (Poole) Guerreiro, who was more like a daughter to her, and Ronda’s husband, Patrick; and her grandchildren, who were her true pride and joy Emma, Ryan, Alec, and Levon. She is also survived by her sister, Debra (Poole) Swanson and her husband Steven Swanson; her nieces Christina (Swanson) Robert and Melissa (Swanson)Bateman; and was predeceased by her brother, Charles W. Poole Jr. She was deeply loved by many close friends, including Mary Gianakis, her “Goddess sisters,” her fellow parishioners and close friend Father Phil Kuhn, and her extended family. All who knew her will carry her memory forward with gratitude and love.
A Celebration of Diane’s life will be held at Conley Funeral Home, 138 Belmont Street, Brockton, MA, on Thursday, September 18, from 4-7pm, where those who knew and loved her can gather to honor a life so beautifully lived. Her Funeral Service will be held on Friday, September 19, at 10am at Trinity Episcopal Church, 120 N Main Street, Randolph, MA. Her burial will take place on Monday September 22, 2025 at Massachusetts National Cemetery in Bourne, MA at 10:30am. Family and friends are invited to attend.
Though Diane is no longer with us in person, her love, laughter, and spirit will remain forever in the hearts of those she touched. In lieu of flowers, please consider donating in Diane’s memory to Dana Farber Cancer Institute or My Brother’s Keeper, both organizations she deeply valued.