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Chelsea's biggest summer transfer mistake revealed

22 Sept 2026 08:06 BST |
4 min read

© IMAGO

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Chelsea addressed a host of big issues in the transfer market over the summer and while they have endured a mixed start to the new campaign, their business can’t really be faulted.

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Morgan Rogers has already established himself as one of their best signings of the BlueCo era and the benefit of adding experienced duo Danny Welbeck and Jordan Henderson to the dressing room will be felt in due course.

Meanwhile, Chelsea’s loan business was also excellent. Ryan Kavuma-McQueen and Reggie Walsh are impressing for Portsmouth and Wigan Athletic respectively, Shumaira Mheuka has already endeared himself to the Celtic fanbase, and Harrison Murray-Campbell is now a regular for KV Kortrijk.

However, it is a different story with Jesse Derry.

The England U20 international joined Chelsea’s academy from Crystal Palace last summer and he was outstanding during his debut campaign at Stamford Bridge, registering 16 goal contributions in 29 youth-team matches for the Blues.

He was rewarded with three first-team appearances before the end of the season and Chelsea were quick to finalise a loan agreement with Sporting CP in a bid to fast-track his development.

It was seen as an ambitious move at the time, given Derry’s lack of experience and the quality of Sporting’s squad, but Chelsea opted to ignore these red flags.

However, after two months in Lisbon, the transfer already looks like a major error.

Jesse Derry transfer error

The main reason behind any loan move is to experience regular football, with the parent club eager for their player to further their development by playing consistently.

With Derry, given he is still only 19 years old, that was the only reason behind his temporary move to Sporting.

He easily could’ve remained in Chelsea’s academy set-up and fought for substitute minutes with the likes of Jamie Gittens, Estevao Willian and Geovany Quenda, but the Blues were desperate for him to experience senior football.

Jesse Derry, Sporting CP
© IMAGO – Jesse Derry, Sporting CP

After a promising pre-season, the early signs were encouraging, however Derry is now firmly down the pecking order.

The England youth international has only made three appearances so far this season, racking up 27 minutes of action from a possible 720, and he has been an unused substitute in each of Sporting’s last four matches across all competitions.

Luis Guilherme, Nestory Irankunda, Flavio Goncalves and Geny Catamo are all favoured ahead of Derry by Sporting boss Rui Borges, and while the Englishman’s lack of game time is far from Chelsea’s biggest concern following their 3-0 defeat to Brentford, it is beginning to become a major issue.

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