Gloria R. (De Silva) Jolley Obituary (1944 - 2026)

**Gloria Roselie Jolley-(Joy)** of Boston, Massachusetts, was born on December 27, 1944, to Dominga and Manuel De Silva of Cape Verde. She was the youngest of five siblings: the late Marie Sylvia (Sybil), DeSilva, and Manuel “Sonny” DeSilva. Gloria attended Saint Francis DeSales grammar school and Girls high in Roxbury. Her first job was as a model for Bonwit Teller, showcasing clothes for the upper class. Gloria was married to Richard Jolley and had two children. Brian DeSilva and Renee Jolley, along with one grandchild, Tonji Hampton. A dedicated community organizer, Gloria worked under Sarah Ann Shaw and Gloria Fox. She worked as a nursing aide at Jewish Memorial Hospital, then Deaconess Hospital, and considered pursuing that career before transitioning to the Massachusetts Bay Transportation Authority (MBTA), where she became known as "Jolley." Throughout her 23 years at the MBTA, she worked her way up from bus driver to collector, and finally to customer service for The Ride at the downtown headquarters, before retiring in 2026. Gloria touched the lives of many people, both young and old. She had a unique ability to build relationships through storytelling and laughter, making even the briefest interaction feel like family. Her home served as a common gathering place for family and friends, both new and old. Whenever she was given the opportunity to give back or care for others, she provided what was needed and, if you were fortunate, what you wanted. Visitors to her home, you did not leave empty-minded or empty-handed. Known for her outspoken nature, whether positive or negative, Gloria offered words of wisdom and loved discussing the history of Africa and Cape Verde. She was also passionate about sharing scientific facts about the world. Gloria enjoyed trying new things and often took children along, regardless of how far or how unconventional the adventure might be. She excelled at planning and organizing outings, one of her proudest accomplishments planning and hosting a tribute to Dudley Station, commemorating the closing of elevated Orange Line trains. This event became a sentimental moment for the community, made possible by her thoughtfulness. Additionally, she organized a trip to Cape Verde to bring her ailing father back home to be care for by family, accompanied by her brother Sonny. Other memorable experiences included organizing family trips, especially for the children, to the museum, boat cruises, the Topsfield Fair, for them to experience riding camels and elephants, and many more fun adventures. It was very important to her to show the children the history of Boston by visiting the many statues in the Boston area, that honor important black figures, such as A. Philip Randolph and among many others. She was a passionate advocate for her children and grandchild. She once took the City of Boston's education department to court after they misdiagnosed one of her children. After a year-long battle, she won and allowed her send her child to a school that better suited her needs. In 1976, she serve on the parent board that helped shape the newly reformed Chapter 776, which aimed to humanize the education of students with disabilities in public schools. After bravely battling breast and kidney cancer, Gloria ultimately lost her fight against lung cancer. She transitioned peacefully, surrounded by her family at home, on March 28, 2026. Her children survive her, Brian DeSilva and Renee Jolley; stepchildren Richard Jolley Thorne, Deidre Sligh, and Keith Sligh; one grandchild, Tonji Hampton; and sisters Phyllis DeSilva-Pearson (and husband Leonard) and her twin sister, Carol DeSilva. She also played a maternal role in the lives of many children not her own, including Kojo Sam from Ghana, Richard Prophete, and Stephanie Perez, to name a few. Nieces and Nephews: Kenneth Mack Jr. (and wife Sharon), Fredrick DeSilva and (wife Janet), Tyrone DeSilva, Angela Mack, Stacey Mack, David Scott DeSilva (and wife Karen), Monique DeSilva, Leonard Pearson Jr. Gloria was loved by all and will be missed by all!