Manchester City could be set to lose one of their brightest academy prospects, Reigan Heskey, with the teenager reportedly on the verge of leaving the club on a free transfer.According to a report from Football Insider, the highly-rated winger’s scholarship agreement expires on June 30, leaving his long-term future at the Etihad Stadium in serious doubt.DOWNLOAD THE OFFICIAL CAUGHTOFFSIDE APP FOR ALL THE LATEST & BREAKING UPDATES – STRAIGHT TO YOUR PHONE! ON APPLE & GOOGLE PLAYReigan Heskey could leave Manchester City on free transferManchester City are facing the prospect of losing Heskey after talks over his first professional contract stalled.The 18-year-old’s current scholarship deal is due to expire, meaning he could become a free agent if no agreement is reached.The uncertainty has alerted a number of Premier League and European clubs, with several teams reportedly monitoring the winger’s situation and ready to move should he become available.For City, losing one of the academy’s standout talents without receiving a transfer fee would represent a significant setback.Who is Reigan Heskey?The son of former England international striker Emile Heskey, Reigan joined City’s academy at the Under-8 level.TeamAppsGoalsAssistsMan City U18402311Man City U2132913Man City Youth League1591Man City (First Team)100Total884125Reigan Heskey career stats via TransfermarktCapable of playing across the front line but most effective cutting inside from the left, Heskey enjoyed a remarkable 2024/25 campaign, registering 27 goals and nine assists as City won both the Under-18 Premier League North title and the FA Youth Cup.He continued his development with the Elite Development Squad during the 2025/26 season, recording four goals and 11 assists in Premier League 2 before earning his senior debut under Pep Guardiola in a Carabao Cup victory over Huddersfield Town.Could Manchester City repeat the Cole Palmer mistake?Losing Heskey on a free transfer would be a significant blow to City’s academy structure, drawing immediate comparisons to the club’s past recruitment errors.Palmer struggled for consistent first-team opportunities at Manchester City before completing his move to Stamford Bridge, where he quickly established himself as one of the Premier League’s standout attacking players.Want more CaughtOffside coverage? Add us as a preferred source on Google to your favourites list for news you can trustWhile Heskey is still at a much earlier stage of his career, City will be keen to avoid another situation where one of their most promising academy graduates flourishes elsewhere after leaving the club.With time running out before his scholarship expires, the coming days could prove decisive in determining whether Manchester City retain one of the brightest talents in their academy or watch another highly-rated youngster continue his career elsewhere.The post Report: Manchester City set to lose 27-goal attacker as contract talks stall appeared first on CaughtOffside.