One thing becomes clear in the summer and winter windows: very few people within Chelsea FC seem to know what they’re doing. Their supposedly amazing sporting structure and the multiple directors involved in transfers, every window provides a new array of head-scratching decisions and leaks that make everyone involved look subpar. The Athletic’s transfer roundup DealSheet from June 2 has the latest Chelsea transfer reports on over a dozen different players, and it isn’t a good look.
Read More: Every Chelsea Player Going to The 2026 World Cup
Chelsea Transfer Reports Indicate a Lack Of Strong Planning
Squad Bloat & FOMO
The Blues failed to get any European football for 2026/27 meaning they’re looking at a campaign of around 40-50 matches, depending on how far they advance in the cups. With that, their squad that was built to compete in the Club World Cup and multiple competitions is bloated with a number of fringe players who are unlikely to get many minutes.
Despite that, the reports from today show that the club are dilly-dallying over a number of players who need minutes to develop or need to be cut loose. They want to keep Josh Acheampong and Mamadou Sarr, but they also want to keep Tosin Adarabioyo, Levi Colwill is untouchable, Wes Fofana and Trevoh Chalobah aren’t mentioned as being on the market. Oh, and the club want to sign a starting level centre-back.
Read More: Every French Player to Play for Chelsea In the Premier League Era
So, for either two or three centre-back spots you could be looking at at least seven different options (not to mention Reece James could play RCB in a three and Jorrel Hato the left). Where are the minutes expected to come from for Acheampong and Sarr? These young players need to play to develop or raise their value but Chelsea would rather keep them around on the fringes by the looks of things.
Read More: Best Chelsea Players to Wear the Number 20 Jersey Ever
There’s no mention either on what the plan is for the overloaded attacking area, Pedro Neto, Estevao, Alejandro Garnacho, Jamie Gittens, and Geovany Quenda are all expected to compete for two spots on the wing, with Cole Palmer also possibly in the mix. There should already be something in mind for trimming these numbers or someone like Quenda faces a wasted year watching from the bench.
Indecision & Lack of Planning
The midfield area is a big question mark for the upcoming season and once again, the DealSheet makes it seem like the directors don’t know what to do. They want to keep injury-prone and out-of-form Romeo Lavia, they might sell Andrey Santos and Enzo Fernandez but aren’t sure and haven’t made a decision which makes one wonder who they want to partner Moises Caicedo next season when they don’t even have any idea how to trim the options, given they’re going to play fewer matches. Dario Essugo is also there and struggled for minutes with the swathe of games in 2025/26. How can he, Lavia, Santos, Enzo, and Caicedo all get suitable minutes?
The same goes for the striker spot. Joao Pedro is the in-form first choice option, but around him, the sporting structure can’t decide the obvious pick between Liam Delap (two goals last season) and Nicolas Jackson. In addition, they haven’t decided what to do with Marc Guiu who has barely played in his two years around the team, just let him go! He won’t play or develop in the team. Why hasn’t a decision already made about his future? And to make matters worse, Emmanuel Emegha is joining on a pre-agreement, meaning there will be five strikers for one position, with no European football.
Read More: Projected Chelsea Squad for 2026/27 as of May 26
Fans have to wonder how the squad planning has been so bad that there’s no clear way to cash in on the player trading, there’s no development pathways for young talents, and there’s no certainty over the ideal 11 or squad of 18 to take into the new campaign.
The same goes for the goalkeeping position. This is a headache that’s been brewing but the return of Mike Penders means the Blues are staring down the barrel of having an unconfident Rob Sanchez share the first-choice jersey with a young Belgian acclimatising to the league. A good team would make a strong decision and work to it, either stick with Sanchez and loan Penders again or go all in on Penders and sign a veteran backup who can help him out. But that would be too much for this club; they’d prefer to have their cake and eat it, and another cake, and another one.
Featured Image Credit
IMAGO / Visionhaus
