Caleb Ernest Winston, Jr.

Obituary For Caleb Ernest Winston, Jr.

Caleb Ernest Winston, Jr. was born on October 10, 1947, Clearwater, Florida to Caleb Ernest Winston, Sr. and Mary Annes Winston.

He attended the public schools of Pinellas County and was a graduate of Pinellas High School, Class of 1967. He accepted Christ at an early age and united with Mt. Olive African Methodist Episcopal Church, where he served on many ministries for numerous years. Caleb later joined St. James African Methodist Episcopal Church under the leadership of Pastor Althea Winston, where he served on the Usher Board, with the Breakfast Ministry, as the Church Security and sang in the Male Chorus and with the Sons of Allen.

Caleb was employed with the City of Clearwater Parks and Recreation Department at the Eddie C. Moore Softball Complex, Larkins Funeral Home and Woody’s Funeral Home. He served as a softball coach for many years and traveled for softball tournaments.

Caleb Ernest Winston, Jr. transitioned from this earthly life to his eternal home on May 14, 2026, Clearwater, Florida.

He is preceded in death by his parents, Caleb Ernest Winston, Sr. and Mary Annes Winston, great-grandmother, Catherine Bevells, siblings, Bernice Flanders, Solomon Winston, Mary Evans and Louise Mickens and niece, Voncreaser Winston.

Loving memories will forever remain with…his son: Caleb Hardy (Tonya); daughters: Dionne Winston Houston (Antonio) and Ivy Gamble; devoted special nieces: Felicia Washington (Harvey), Karen Winston Roziers and Pam Conoly; devoted special nephews: John Evans (Katrina), Theroun Winston, Elijah Flanders (Shirley), Jimmy Lee Flanders and Frank Flanders; devoted special great-nephews: Harvey Washington, Jr., Tevin Washington (Ariel), John Evans, Jr. and Jonathan Winston; devoted special great nieces: Leshenda Winston and Misha Winston; grandchildren: Kelvin Jackson, Kyle Jackson, Jondalyn Gamble and Dillon Gamble; friends: Ben White, The Woodys, Don Butler, Jonathan Wade and Maryann Woodard; and a host of other nieces and nephews, extended family, Bishop Rebecca McKay, St. James African Methodist Episcopal Church Family and Alberta Everett Family.

Public Viewing: Friday, May 22, 2026, from 5:00 – 7:00 p.m. at Smith Young Funeral Home, 1005 Howard Street, Clearwater, Florida 33756.

Celebration of Life Service: Saturday, May 23, 2026, at 1:00 p.m. at St. James African Methodist Episcopal Church, 1436 S. Madison Avenue, Clearwater, Florida 33756.

Services Entrusted To The Care of Smith Young Funeral Home – 727-442-2388.

Send flowers to the service of Caleb Ernest Winston, Jr.