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Young Chelsea star loved by John Terry set to leave the club this summer
Chelsea have made a habit in recent years of signing some of the most promising young talents from around the world.
Over the past few seasons, the Blues have spent heavily to bring in the likes of Sporting Lisbon duo Geovany Quenda and Dário Essugo, Belgian goalkeeper Mike Penders, and a host of Brazilian prospects — including Kendry Páez, Deivid Washington, and, perhaps most notably, Estêvão Willian — spending vast sums on relatively unproven players.
At the same time, however, the club has continued to offload some of its finest homegrown academy products.
Last summer, Conor Gallagher was sold to Atlético Madrid despite an excellent season, Lewis Hall joined Newcastle United and helped lift the League Cup, and Ian Maatsen moved to Aston Villa. The previous year saw Mason Mount head to Manchester United, and Callum Hudson-Odoi to Nottingham Forest.
Other academy graduates such as Fikayo Tomori, Tammy Abraham, Billy Gilmour, and Marc Guéhi have also been sold in recent years — many of whom Chelsea may now regret letting go, especially given the team’s inconsistent performances under Enzo Maresca this season.
Now, another highly rated academy talent looks set to follow them out the door.
Castledine Set for Permanent Exit
Leo Castledine. (Malcolm Couzens/Getty Images)
According to a report from The Athletic, Chelsea are preparing to sell 19-year-old midfielder Leo Castledine this summer.
The England Under-19 international has spent the 2024/25 season on loan at League One side Shrewsbury Town, where he made 26 appearances across all competitions. While the Blues rate him highly, the club are open to offers and will include a sell-on clause in any potential deal. Several Championship and League One clubs are reportedly interested.
Castledine himself is said to be keen on leaving Stamford Bridge in search of regular senior football, though he still holds strong affection for the club.
Chelsea haven’t completely ruled out another loan move, but a permanent departure is currently seen as the most likely outcome.
Castledine earned praise from club legend John Terry following his senior debut in January 2024. Writing on X, Terry said: “Congratulations Leo. Love him and so will the Chelsea fans, he is like a magnet in the box.”
Another day, another academy gem slipping through Chelsea’s fingers.
