Rupert Bailey

Rupert Bailey, AKA "Sherif," passed away peacefully at his home in Meriden, Connecticut, on Thursday, April 17, 2025, at the age of 78. He was the beloved husband of Teslyn Bailey and a cherished father, grandfather, brother, and friend.
Born in Grewaley, Westmoreland, Jamaica, Rupert was the fifth child and third son of the late Enoch and Albertha Bailey. Known for his loving heart, hardworking spirit, and endless generosity. Rupert was a pillar of support for his family and friends and always someone you could count on. He was incredibly talented, and his skillful hands could fix almost anything.
Besides his wife, Teslyn, Rupert is survived by his four children, Mark, Kemar, Krystal, and Deidre; and his grandson, Markus. He also leaves behind nine siblings: Carmen, Monica, Cecil, James, Beverly, Cherry, Sharon, Carl, and Walford, as well as numerous nieces, nephews, grandnieces, grandnephews, great-grandnieces, great-grandnephews, cousins, in-laws, and a wide circle of friends. Besides his parents, Rupert is predeceased by his brothers Sadie and Lorenzo Bailey.
Family and friends are invited to attend calling hours on Friday, May 9, 2025, from 9:00 AM to 11:00 AM at Cross Street AME Zion Church, 440 West Street, Middletown, CT 06457. A funeral service for Rupert will begin at 11:00 AM. Entombment will follow at Sacred Heart Cemetery Mausoleum, 250 Gypsy Lane, Meriden, CT 06450.
Rupert Bailey will be deeply missed but forever remembered for the love and light he brought to the world. His kindness and generosity touched countless lives, and his memory will live on in the hearts of all who knew him.
For online condolences, please visit jferryfh.com.