Reigan William Stephen Heskey was born on 18 January 2008 in England, the son of former Premier League striker Emile Heskey. He spent part of his childhood in Australia while his father played for Newcastle Jets, before returning to England and joining the Manchester City academy at the age of eight in 2016.
Heskey progressed steadily through City's youth ranks, making an early mark when he appeared for the Under-19 side in the UEFA Youth League in November 2023, aged just 15, scoring in a 3–0 win over Young Boys. Promoted to the Under-21 squad for the 2024–25 season, he announced himself with a hat-trick in 22 minutes on his debut as a substitute in Premier League 2 against Norwich City U21. He also scored his first senior professional goal in the EFL Trophy against Grimsby Town in October 2024.
On 24 September 2025, Heskey made his senior debut for Manchester City alongside his brother Jaden in a 2–0 EFL Cup third-round victory over Huddersfield Town. A direct and mobile forward, he uses his movement and finishing instinct to create and convert chances in and around the penalty area.
At international level, Heskey has represented England at Under-17 and Under-18 level. He scored four goals at the 2025 FIFA U-17 World Cup, netting in group stage wins over Haiti and Egypt before England were eliminated in the round of sixteen by Austria. He earned his first Under-18 cap in October 2025.
Manchester City continue to develop Heskey through their Elite Development Squad, with first-team involvement now beginning to follow.