Olga Pearl (Phillips) Bailey, 87, of Boston, Massachusetts, passed away peacefully on September 18, 2025. Born in Greenland District, Manchester, Jamaica, she was the daughter of the late Alfred George Phillips and Ivy Louise Walters ("Sister Annie") and the beloved wife of the late Clifford E. Bailey. She is survived by her children: Goinette "Pauline" Meade, Jennifer (Magnus Neptune) Bailey, Clive Bailey, Roderick "Ricky" Bailey, Noel Bailey, Beverly Bailey, and Jacquelyn "Jax" Bailey; six grandchildren; her brother, Clive Gladstone Phillips; along with nieces, nephews, and extended family.