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Chelsea's Frustrating Winter Window

Writer's picture: maxwatkins072maxwatkins072

Paul Winstanley and Lawrence Stewart, the Co-Sporting Directors at Chelsea FC. Image Credit: Chelsea FC
Paul Winstanley and Lawrence Stewart, the Co-Sporting Directors at Chelsea FC. Image Credit: Chelsea FC

With the end of the January 2025 transfer window, I briefly revisited the strategy during this transfer period to outline and assess the factors that made January a frustrating month for Chelsea fans.


I do not agree with the sentiment that Chelsea could fix all their recent issues in one window, however, the frustration from fans of the club has been the board's lack of any attempt to address Chelsea’s current problems.


Whether it is the panicked recalls from various loans or the selling/loaning of players who have only been at the club for half a year, it seems like this window has been about damage control over the misfire transfers from the board's past


The transfer that summed up the cluelessness that is apparent at Chelsea was the six-month loan of Joao Felix to AC Milan. With a loan fee of £6m, it does not look too bad initially. Felix picks up some much-needed consistent game time and Chelsea loses a player and part of their wages for six months with £6m going back their way. However, with the context that this was a player that the club bought for £44m less than six months ago in a swap move with Connor Gallagher, questions start to arise. Especially when Felix failed to impress in his first six-month spell at the club under Graham Potter and Frank Lampard.  


Cesare Casadei departed later in the window to Torino for £12.5m with a 25% sell-on clause. In 2022 the Italian midfielder was bought by the Blues from Inter Milan for £12.6m with a potential £4.5m in add-ons. Therefore, after two and half underwhelming years spent in England, Casadei lost Chelsea at least £100,000. Whilst it is far from the worst signing of all time, it is another example of the board using this window to attempt to clean up the failed signings from previous windows.  


I understand that with Chelsea’s strategy of gambling on youngsters, ultimately losing money would seem inevitable. My issue, however, is that after making the mistake of pursuing the wrong gamble, they make the same mistake again. At the time of writing, Chelsea is close to signing Mathis Amougou, a player with good potential but has only started nine league games for Saint Etienne, for £12.4m. Does the Fee seem familiar?  


This is not trying to put down a 19-year-old who has not even signed for the club yet, instead, it is to point out the ridiculousness of the situation. An issue Chelsea on the pitch has struggled with has been a loss of depth in the midfield due to injuries and poorly timed loans. Amougou not only has worse midfield statistics than his Ligue 1 counterpart, Andrey Santos, but he is not even getting a chance under Maresca and is planned to move on loan to Strasbourg.  


The winter window is full of panicked-induced decisions and poorly made choices. Fans who want the club to sign big names that will fix every issue on the pitch have a desirable optimism. That being said, it is a delusion within the board that they can easily correct their mistakes from the past solely in this window, especially as they are already making the same mistakes again a week into February.  

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