Debra “Debbie” O’Brien Cannata
Debbie was called home to our Lord on Wednesday, June 17th, 2026. She was surrounded by all of her loved ones and her cherished dogs as she departed. She was greeted at heavens gates by her parents, Thomas and Mary (Schutt) O’Brien of South Boston, her sister Mary O’Brien, her beloved daughter, Jillian Heaslip, nephew, Mark Walsh and her dog, Caesar.
Debbie will be remembered and loved always by her long term boyfriend (or common law husband as she would say) Robert St. Hilaire, her daughter, Lisa Heaslip, her sister’s Pauline Walsh, Kathleen Cannata, and Maureen Kelleher as well as her favorite brother-in-law, Tim Kelleher and the son she never had but always wanted, Christopher St. Hilaire. She will be deeply missed by her three grandchildren that were her pride and joy and her whole heart, Max Driscoll, Jaelynn Dasilva and Bobbi Boyns as well as her bonus kids and all her nieces and nephews. Her favorite boys, her dogs, Teddy and Shiloh will be given extra treats in her name, daily.
She was born April 4th, 1962 in Dorchester, Mass and spent most of her life in between South Boston and Dorchester. Family has always been the most important thing to Debbie and she always reminded her sisters, children and grandbabies to “Listen, you gotta stick togetha and take care of each othah! Promise me?!” If you knew her - you know!
Debbie lived to love and care for others. She was a PCA for many years caring for sick and disabled people and their families and she took a lot of pride in her work and helping people.
Debbie made the best brownies and meatballs in all of Boston and she was going to insist you try them or anything she had made, for that matter. She loved to share anything she had with those she loved.
She had an infectious laugh and a way of lighting up any room she entered with her big blue eyes and even bigger smile. Never too shy to make a new friend, she was an avid storyteller and would laugh so hard herself while telling it you couldn’t help but laugh right along with her.
She will be deeply missed by everyone who knew and loved her but the memories and laughs she left will forever live on in their hearts.
To honor Debbie, a celebration of life for her family will be taking place at a later time. In lieu of flowers, donations can be made in her name to the Granada House at https://www.granadahouse.org/general-4.