Phyllis Marie Malatesta Smith passed away peacefully on April 17, 2025, at her home in Havenside, with her devoted daughter Kerin O’Brien and son-in-law Michael Duffey by her side. She was 93 years old.
Phyllis’ journey in life began in Medford, as the firstborn daughter of Jeanette (Doran) and Albert A. Malatesta in 1931. Her younger brother, Albert (“Bert”) Malatesta, soon followed in 1937, and they shared a deep and loving sibling bond throughout her life. She spent her younger years attending Medford schools, spending wonderful and memorable times with her friends, camping each summer with family, and learning business education at Medford High School. She graduated in 1948, and went to work at John Hancock Financial in Boston as a secretary. She married Joseph E. O’Brien, and gave birth to her son, Charles Richard O’Brien, and her daughter, Kerin Mary O’Brien.
Phyllis moved to Falmouth in 1971 with her children and second husband, Phil O’Rourke, who introduced the family to sailing around Cape Cod, the outer Islands, and the Caribbean, giving her a lifelong love of the ocean, beach, sailing, and a quiet, relaxed way of life she truly loved. Phyllis’ love of the Cape and Islands was all-encompassing, and her family spent many happy years by the sea and beaches. Phyllis was a great lover of the arts, collecting paintings, antiques, and art glass, and listening to music; she was a voracious reader throughout her life.
While living on Cape Cod, Phyllis left the business profession to train as a social worker. She worked for Pocasset Mental Health, an inpatient facility for people with mental illnesses, and at Stepping Stone, a program to help mentally challenged individuals prepare to live their lives independently, a job very close to her heart.
One of her strongest skills was crisis intervention and emergency care for those who wanted to end their lives. She was instrumental in working with the Samaritans Suicide Prevention Program in putting up suicide prevention barriers on the Bourne Bridge.
Phyllis was extremely proud of her work helping others overcome life’s difficulties. She had a generosity of spirit, empathy, and compassion that was unmatched, and a unique ability to make everyone around her feel loved and valued. She is sorely missed by all who were lucky to know and love her.
While working as a social worker for Massachusetts, Phyllis met and eventually married the love of her life, the Rev. David Emerson Smith, who also worked for state mental health services. From friendship and mutual respect grew a wonderful love story filled with laughter, joy, and devotion. Phyllis cherished her years with her husband David as her happiest and most joyful. The devotion and love they had for each other was clear to anyone who saw them together. They shared a love for adventure and a curiosity to learn and see new things. They loved nothing better than hopping in the car to go “gunkholing,” exploring the coast of Maine and Martha’s Vineyard, often stopping to go antiquing along the way. They both had a love for exploring, but were equally happy staying home to listen to an opera, or going walking with their beloved dog, Rosco.
Phyllis and David moved to Martha’s Vineyard from Maine in 2007, having both retired, and eager to join an Episcopal community where they could be of service. David was able to fill in as a pastor at Grace Episcopal Church when needed, as well as work in hospice care. Phyllis served on the vestry and many other committees at Grace Church. They both desired a life of service to others, and found their home at Grace Church on Martha’s Vineyard. After David passed away, Phyllis was committed to continuing her service to the church and community. She formed and chaired a successful group for people experiencing grief, and was an active member of the Women’s Discussion Group. A group she was delighted to volunteer for was Friday Night Lobster Rolls, at which she helped prepare, serve, and sell thousands of rolls over many years, which benefited the church and community. She loved being a part of this group with her friends from the church.
Phyllis was a beloved member of the Havenside community, and loved the residents, especially her friends in Building B. The manager, Lucinda Kirk, and Jerimiah Miller were always there if she needed help. She often spoke of how incredibly lucky she was to be surrounded by such wonderful, caring neighbors. Before she became ill, she was always available to lend a hand, stop for a chat, or help organize dinners and parties. Being part of the Havenside community was very meaningful for Phyllis.
A series of falls starting several years ago left Phyllis severely disabled, with brain injuries that impacted all areas of her life. She coped as best as she could with the help of her family and friends. Even in her end-of-life struggles, Phyllis never lost her special spark, sense of humor, infectious laughter, and compassion. Her ability to make everyone around her feel cared for never wavered. Her gratitude to her daughter Kerin, and all who cared for her while she was ill, was genuine and deep.
Phyllis was predeceased in 2011 by her beloved husband David, and he lived forever in her memories. Not a day passed without memories of the remarkable and unique love and life they shared together. These memories sustained her throughout, and she often referred to David as her “rock” in life. She is survived by her beloved “Big Brother” Bert and his wife Barbara; her loving, devoted, and supportive daughter, Kerin and her husband Michael, her son Charles and his wife Gail, her grandson Eric, and her long-term best friend, “Aunt” Jane Malatesta. Phyllis fully embraced and loved her role as stepmother to John Smith and his wife Debbie, Tom Smith and his wife Alison, Laura De Bettencourt, Paula Smith and her husband Drew, the late Michael Smith, and her many wonderful grandchildren.
A funeral service will be held for Phyllis on Saturday, June 14, at 11 am at Grace Episcopal Church in Vineyard Haven. In lieu of flowers, please consider donating to Hospice and Palliative Care of Martha’s Vineyard, online at hospiceofmv.org/donations.
