James W. Bailey was born in Boston, MA on October 4th, 1962, to the late Margaret F. Bailey and the late Lawrence S. Bailey. He was the last child of 11 children. James departed this life on August 30, 2021, because of a long-term illness.
James grew up in the South End, where he attended and graduated from Charlestown High School. He was very popular and well known by many as “J.B,” the boxer and a Master Chef. If James was your friend, you could guarantee you had a friend for life.
James enjoyed spending time with his family, playing cards, listening to music, and enjoying life to the fullest.
He was a father who bragged constantly about having 3 sons of his own. He always would say having his 3 sons was like “knocking someone out in the boxing ring” He was proud grandfather to his 4 granddaughters and 1 grandson.
James leaves to cherish his memory, his 3 sons James, Harold, and Samuel Randall, their mother Roneka Randall, his grandchildren Janiya Randall, Jalila Randall, Arielle Randall, Lyric Williams-Randall and Corey Tucker; ex-wife Rondella Washington and step son Maceo Crowder. His late siblings, Margaret Roisten, Noah Roisten, Samuel Bailey, and Daniel Bailey; his surviving siblings Cora Lewis, Virginia Davis, Maudeana Strumph, Shirley Bailey, Sylvester Bailey, Lorraine Keyes, and a host of nieces, nephews, and cousins who loved him dearly.
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