Obituary of Dudley Winfield Bryan, Sr.

Dudley Winfield Bryan was born in Roadview, Saint Peter on June 11, 1940. He departed this life on October 4th, 2019. He leaves to mourn a daughter, a son, grandchildren, brothers, sisters, nieces and nephews. He will be missed by many others on the island who called him “Major”.

He grew up in Barbados, son to Rose Etheline Bryan and Arthur Ifill, where he made a living spearfishing and cutting cane, while contributing to the family after his mother immigrated to the United States. In his spare time, he painted, wrote songs, and ran a local gym. At 27, he travelled to America, first to Florida and later to Massachusetts, where he rejoined his mother Rose and adopted father Cleophas. He then met his wife Lillie at 29, and together they raised a daughter and a son, as he became a dutiful husband, father and member of the church community in the years that followed. He attended various churches over his long life, including Church of the Nazarene, Shawmut Community Church of God, and Jubilee Church, assisting on occasion as an usher, van driver, and small group host for bible studies at the family home.

With a generous recommendation from his father-in-law Cleophas, Dudley and his brothers began employment at the Coca-Cola bottling company shortly after arriving in Massachusetts. As a truck driver and porter, he worked there for over 40 years as an exemplary employee setting new standards in dedication. Additionally, Dudley explored entrepreneurship by selling licensed insurance and health products through partnership with various companies.

In his leisure time, Dudley enjoyed a wide spectrum of interests. He briefly studied architecture at Wentworth Institute and his love of painting was readily apparent to those that knew him best. He was an aspiring model and continued his love of bodybuilding throughout his life. He wrote numerous songs and had several professionally recorded. He could always be heard singing as he prepared breakfast on Saturday mornings. He became an avid bowler in a league and won numerous trophies. During his time at Coca-Cola, he enjoyed bringing home foreign coins to add to his daughter’s growing collection. He especially loved cooking (fish cakes, cou cou, bakes, split peas and rice).

At age 59, he and his wife divorced, and he ultimately pursued his dream of retiring to Barbados, returning to the family home in Roadview. He spent his retirement time re-discovering his love of Barbados, enjoying his time swimming, dancing and spending time with friends new and old. 

He is survived by his two children, Lisa Stringfellow and Dudley Ablorh-Bryan, their mother and former spouse Lillie Bryan, three grandchildren, Michaela, Althea, and Benjamin Stringfellow, his brothers Edward Bryan and Henry Bryan, sister Cleo Thompson, and numerous cousins and extended family members in both the United States and Barbados.