There are a few transfer windows that have been pivot points for Chelsea. The 2017/2018 windows are still hanging around Chelsea’s neck.
When Chelsea won the Premier League in 2014/2015, Jose Mourinho demanded they build on their success instead of linger in it. The board ignored him and the squad proved stagnant the next season. One would think the board would learn from that situation, but the 2017/2018 transfer windows showed that they had failed to learn anything at all from the past.
Antonio Conte wanted particular players to strengthen after his emphatic title win. The board nodded politely while selling players out from under him and bringing in the bargain bin versions of the players he asked for. The window itself is not what caused Chelsea to fall to fifth that season, but it played a big part.
Almost every single transfer made in those two windows is hanging around Chelsea’s neck. The Blues paid too much and gave wages too high for players that have mostly done nothing for them. Because of those high wages, the Blues are struggling to move on from those disastrous times.
But first, there were good transfers during that time period. Willy Caballero has been a fine backup keeper as he replaced Asmir Begovic. Antonio Rudiger started somewhat unevenly but is now Chelsea’s best center back. Ross Barkley, Olivier Giroud, and Emerson have all taken time to break into the squad but all three have shown themselves to be very worthwhile transfers (and Barkley and Emerson will only improve). Billy Gilmour and Ethan Ampadu also arrived during that season, though they fit more into the academy than the first team.
But nearly every other player that came in that year was supposed to be a starter or major contributor and they have failed to be either. Davide Zappacosta has probably been the best of the lot which speaks volumes. Alvaro Morata started very well, but an injury and low confidence caused him to fall off the wagon and never get back on. Danny Drinkwater spent nearly his entire first season injured and his entire second season completely untrusted. Tiemoue Bakayoko came in injured and was forced into action far before he was ready.
The Bakayoko situation shines the light on how poor some of the sales were. Say what you will about Nemanja Matic, but Conte wanted him to stay to ease Bakayoko in to the side. But the board failed to convince Matic (or Nathaniel Chalobah) that they would have playing time and suddenly Conte had no choice but to throw Bakayoko into the deep end with an injured leg.
Two promising players in Bertrand Traore and Nathan Ake also departed in those windows. Buybacks are rumored on both but those bridges may have been burned. Traore, like Romelu Lukaku before him, saw the board more interested in buying new players than giving him a shot. Ake had returned from loan only to spend the next half season on the bench so it is unsurprising that he got out.
And of course, the myths around Diego Costa, rightly or wrongly, burdened the club. Costa had wanted out in January of 2017. When Conte texted him that summer, it was not Conte pushing Costa out so much as it was confirmation of what Costa wanted. But Costa threw a fit for six months as he tried to shift the blame on Conte. It worked among some fans and even though Costa’s form at Atletico Madrid has been mostly nonexistent, he still has his supporters that refuse to believe the actual time line of events.
Chelsea has salvaged the good players they could out of that season’s transfer windows. The rest they are trying to move on now but it is proving difficult. Zappacosta should be moving to Italy any day now as he has failed to be more than “just ok” for Chelsea. Morata is out on loan with a buy clause at Atletico Madrid. Drinkwater has plenty to prove yet but his wages are prohibitive to the clubs that might want him after not playing for a full season. Bakayoko will have suitors, but only weary ones concerned about his up and down form and his attitude issues that pop up from time to time.
But regardless, Chelsea will take a loss on these players after they paid too much in transfer fees and wages. This is largely because they failed to learn the lessons of Mourinho’s 2015/2016 season. The Blues are still paying for that and they need to show that they learned the lessons of Conte’s 2017/2018 season when they are able to buy players once more.