Sales are more expected at Chelsea in the January transfer window over purchases, and it appears the Blues are about to cash in on one of their in-form youngsters.
Chelsea spent north of £250m in the summer on players like Joao Pedro, Liam Delap, Jamie Gittens and Alejandro Garnacho. So, despite the arrival of manager Liam Rosenior, the chances of signings are small.
That is, even if Rosenior has identified Strasbourg’s Valentin Barco as a key target. Exits are much more likely with AC Milan in talks to add to their growing Chelsea contingent with the signing of Axel Disasi.
Chelsea’s stance on January transfers under Liam Rosenior is clear 🗣️
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Chelsea's January transfer window stance
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Now, Fabrizio Romano has reported on X that out of nowhere, an in-form Chelsea youngster is about to complete a permanent move to one of the Championship’s best, promotion candidate Middlesbrough.
Fabrizio Romano confirms Leo Castledine set for Middlesbrough
After a disappointing loan at Shrewsbury, 20-year-old Castledine joined League One side Huddersfield Town in the summer on loan for the 2025-26 season. He is considered one of the division’s best players.
Leo Castledine applauds the fans after Huddersfield Town against Newcastle United U21 in the Vertu Trophy.
Photo by George Wood/Getty Images
His form has been superb. The London-born gem has clocked up 17 goals and assists for Huddersfield in the first half of the season, in just 27 appearances. Scoring 12 goals himself, Middlesbrough have moved.
According to Romano, Castledine is set for a permanent move to Middlesbrough as the Teesside club look to bolster their push for automatic promotion after losing manager Rob Edwards to Wolves.
Romano posted: “EXCLUSIVE: Middlesbrough agree deal to sign Leo Castledine from Chelsea on permanent move, here we go. Permanent deal proposal with sell-on clause all agreed with Boro.”
£1m is far too CHEAP for Leo Castledine, isn’t it? 🫨
He's set to join Middlesbrough in a bargain permanent deal…
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Ben Jacobs confirms Middlesbrough are paying a tiny fee
While Chelsea fans won’t begrudge Castledine for jumping ship after managing just one senior appearance for the Blues, they will feel aggrieved by the fee Chelsea are set to receive for Castledine.
Despite his stunning form in England’s third tier for one of League One’s biggest, Boro will only be paying £1m for Castledine up front. That is according to Ben Jacobs, who says he’s agreed a contract until 2030.
Jacobs reported: “Fee in excess of £1m. Understand Castledine has agreed a 4.5-year contract. Chelsea retain a sell-on. Multiple Championship clubs interested, but Castledine sold on Middlesbrough project.”
It is the first bit of business done since Rosenior took charge at Chelsea and while he is unlikely to have been involved in the decision making, he will surely have been notified by the decision to cash in.
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