Shawn Hilliard

Shawn Hilliard ObituaryObituary published on Legacy.com by O'Brien Funeral Home - South Boston on Mar. 3, 2026.Shawn Hilliard, born on February 5, 1975, passed away peacefully surrounded by family on March 1, 2026. He was a devoted husband, father, son, brother, uncle, and friend whose generosity, humor, and love for his family and community defined his life. He was known for his warmth, loyalty, and natural ability to bring people together.Born and raised in South Boston, Shawn grew up deeply connected to his neighborhood and remained rooted there throughout his life. He was a lifelong member, supporter, and staff member of the South Boston Boys & Girls Club, where he built lasting relationships and gave back to the community that helped shape him.Shawn had a deep love for baseball and carried that passion throughout his life, whether on the field, coaching, or supporting the Red Sox. He attended opening day with friends and family every year.He loved hosting gatherings with friends and sharing laughs over a few (or more) drinks. He never met a drink menu he couldn't conquer, and is the sole name on a plaque honoring that accomplishment at Campy's Bar at Ellis Haven. He loved taking spontaneous trips to Florida and drinking his way around Epcot, which has now become a tradition for family and friends at least once a year.Above all, Shawn was devoted to his family. He shared a lifelong love with his wife, Jill, who had been his best friend since the day they met in first grade. He took immense pride in his three children Brooke, Allison and Robert and his fiancé Kylie Donovan. He found joy in the relationships he nurtured over the years.Before his passing, Shawn began the early vision for a foundation that will be led by his children, wife, and lifelong friends. The Shawn Hilliard Foundation will continue his legacy of community support and ensure that those who need it receive the same care and opportunity that meant so much to him.Shawn's legacy lives on through the countless people he impacted and the community he loved so deeply. He is survived by his mother Deanna (O'Connell) and the late Robert A. Hilliard. Beloved husband of Jill (Costello) Hilliard. Devoted father of Brooke Hilliard, Allison Hilliard and Robert Hilliard and his fiancé Kylie Donovan. Cherished brother of Kevin Hilliard and his wife Janet, Shannon Reuben and her husband Donald. Son-in-law of Patricia Costello and the late Edward Costello. Brother-in-law of Kim Giordano, Dawn Warwick and Edward Costello. Also survived by many nieces and nephews.Visitation in the O'Brien Funeral Home 146 Dorchester St South Boston on Thursday March 5th from 4-8pm. Funeral Mass in St. Monica Church 331 Old Colony Ave South Boston on Friday March 6th at 10am. Relatives and friends are kindly invited to attend.In lieu of flowers, donations may be made to The Shawn Hilliard Foundation to continue his commitment to supporting the community he loved. All donations can be made by visiting https://www.shawnhilliardfoundation.org/To plant trees in memory, please visit the Sympathy Store.