Chelsea have been pretty busy this January already, but it was to sign players. Instead, they parted with Enzo Maresca on the first day of 2026. It was not due to his results on the pitch, which had been poor, to be fair. Instead, it was largely due to disagreements behind the scenes, and now, there are serious questions over whether any manager can last under the constraints of the model put in place by the owners.
That has not stopped them from handing new manager, Liam Rosenior, a six-and-a-half-year contract upon arrival from Strasbourg. That feels more like the club trying to publicly prove their backing rather than a genuine expectation of how long he is expected to last in the role.
On the other hand, the transfer business is rolling on in the background. In fact, a deal has now been agreed, although it is a departure, and not an arrival.
As reported by [Fabrizio Romano](https://x.com/FabrizioRomano/status/2009268408022409305), Middlesbrough have agreed a deal to sign Leo Castledine from [Chelsea](https://theprideoflondon.com/liam-rosenior-wants-argentine-international-first-chelsea-signing) on a permanent basis. The Italian journalist has given the move his famous 'here we go'. The Blues have accepted the proposal with an important sell-on clause included.
Castledine is another highly-rated youngster who is not going to make it at Chelsea. We can only wish him the best of luck at Middlesbrough.
The transfer fee is believed to be a modest £2 million. But it is believed that Chelsea have a significant sell-on clause.
On the other hand, it remains to be seen if the club will back Rosenior with some new signings in this winter window. There are a lot of holes in the squad that need to be filled. In fact, they were there in the summer as well, and one of the reasons that the Blues have been struggling in this campaign is that they were overlooked.