N’Golo Kante sold, Ousmane Dembele miss – Chelsea’s worst case first Todd Boehly transfer window – Daniel Childs

Chelsea fans are not being unreasonable if they approach this window with serious concern. Although this period of the football calendar naturally provokes speculation, excitement and the glamour of a marquee signing, those in west London are well aware of the serious pitfalls too.

You only need to look at the tale of Romelu Lukaku, last year’s saviour now viewed as this year’s problem. The fear of splashing more on attackers only to see their previously transformative traits seep away. The equal fear of a repeat of the academy exodus witnessed in 2021, where several promising talents were used to generate profit, almost matching the price paid for Lukaku.

Thomas Tuchel has stressed the need for a rebuild this summer after the Todd Boehly and Clearlake consortium takeover was completed, the Blues need to replace departing senior figures and upgrade areas of need.

READ MORE:Thomas Tuchel’s stance on Conor Gallagher future as key Chelsea meeting revealed

Though given Chelsea’s shoddy track record in the market over the past five to ten years that has seen a squad assembled under six very different coaches, the clamour for consistency and alignment across all levels of the club has never been more important.

football.london has already looked at the dream scenario for Chelsea this summer, but it’s time to do the opposite and predict what could go wrong in Todd Boehly’s first window.

N’Golo Kante sold and not replaced

With his contract up in 2023 and rumours of Manchester United eyeing up the possibility of a similar deal they struck for Nemanja Matic in 2017, the thought of N’Golo Kante being sold to a direct rival is already unpleasant. Though when you add in the fear that Chelsea once again misses out on the chance to sign a new midfielder, it could prove even more damaging to Tuchel’s plans.

Given the likelihood, that long-term target Aurelien Tchouameni is off to Real Madrid and West Ham’s value for Declan Rice continues to skyrocket, one of the priority areas in Chelsea’s squad could be skipped over-investing in again.

Not signing Rice would be frustrating but weakening your own midfield by selling a player Tuchel has publicly backed as one of his most valuable would be a blow.

Not improving the attack

Many attacking targets have already been mentioned and coinciding with the potential exit of Romelu Lukaku this is a very awkward area for Chelsea to navigate this summer.

Losing Lukaku would take a massive issue off Chelsea’s hands but the overall attack still has question marks and failing to add something new to a troubled area could see this baffling issue persist into the 2022/23 campaign.

Ousmane Dembele, potentially on a free from Barcelona feels increasingly like a deal Chelsea could do to reunite Tuchel with a player he helped get the best out of at Borussia Dortmund. Though more money could be instead spent on other targets who, if not smartly scouted, could fall into the same trap as Lukaku, Timo Werner and Hakim Ziyech of looking unsuited to the demands of the league and system.

Cashing in on Cobham again

A sequel to the pretty irritating Cobham exodus would only weaken Tuchel’s squad and probably lead to Chelsea having to spend more on transfers in the future.

Cashing in on potential fees for Conor Gallagher, Levi Colwill, Armando Broja, Billy Gilmour and more could waste a golden opportunity to uncover internal solutions to lessen the burden on this window’s wishlist and save money.

As Todd Boehly noted in his opening words as Chelsea’s new owner, “developing the youth squad” is one of the key commitments to invest in the club for the long term. Premier League and some European names might offer a tempting offer right now, but as the sales of Fikayo Tomori, Marc Guehi and Tino Livramento proved last season, the current squad could have benefited from those names.