St. George's, Grenada
Winner was born in St. George's, Grenada to a white British father and an Afro-Caribbean mother, and moved to Leicester, United Kingdom at seven years old. Winner is one of three brothers and is the middle child. His older brother is William and his younger brother is named Michael. Michael is often in his corner during his fights and often assists in training. He started in sports during his high school years, competing in football and other athletics. Winner never thought of being a mixed martial artist but loved sports. He went to self-defense classes at Leicester Shootfighters and met Dan Hardy and Paul Daley. Hardy inspired Winner to give the sport a real try.