Chelsea still have £112m transfer dilemma after Ian Maatsen agreement as next deal decided

One down, two to go? Chelsea's left-back overhaul has started, but just where will it stop?

As Ian Maatsen nears an exit for the second time in 12 months, questions of long-term planning for the position are raised once more. Chelsea entered the summer with three natural options of different ages, profiles, and values, but could enter the next Premier League season in totally unrecognisable shape.

Maatsen leaving was always expected. From the moment Chelsea accepted an offer of £30million on deadline day last year from Burnley, it became apparent that they were happy to let him go. For a 21-year-old who had never played a top-flight match, it was deemed too good of a price to turn down.

Maatsen stayed; he wished to fight for his place against Ben Chilwell, returning to fitness during the tour of America after a second injury-hit season in a row, and Marc Cucurella. The latter was actively being pushed out of the door as well.

Cucurella was close to moving to Manchester United on loan as cover for Luke Shaw but was instead named in a Carabao Cup squad, and the deal was scuppered. By January, Maatsen was angling to depart, having been given no real look-in from Mauricio Pochettino, either as a makeshift attacker or in his preferred left-back/wing-back spot.

Chelsea handed him a new contract to ensure that they wouldn't enter the final 12 months of his deal upon returning from Borussia Dortmund, but the £35million release clause also inserted said much. From the moment he was sent out over the winter the chances of making another appearance for the club were slim.

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Now he is set to be the first major outgoing of the summer window. Aston Villa have agreed to a deal worth just under £40million for Maatsen, football.london understands, and talks will continue between the clubs over a player going the other way, though not in a direct swap deal.

That leaves Cucurella and Chilwell, in theory, to battle it out for the first-choice spot under Enzo Maresca. But it's not that simple in reality.

Chilwell started just nine games last season in the league, featuring in only four more from the bench. It was the third year in a row that he failed to make more than 1,500 minutes, and more worryingly, the second time he didn't even get to 900. His injury issues are by now well documented, and at 27, there are serious questions over just how much he can be relied on.

As for Cucurella, even with Chilwell out and the left-back spot seemingly open, he played less than Levi Colwill, who played his last match of the season in early March. Cucurella was also out for a period over the winter but nevertheless only started 20 matches regardless.

His form spiked in the final weeks under Pochettino, when a change of system to crowd bodies in the build-up aided him, but long-term worries remain over the Spaniard, who has a tendency to rush out into tackles. Cucurella still struggles one-on-one, and even with players closer to him in the 3-2 shape Pochettino eventually adopted, his passing lacked incision and threat from wide areas is minor.

Nevertheless, looking at what Maresca may now do, Cucurella is perhaps better suited than Chilwell. Not only does he have a better fitness record of late - not that there's much competition—but he can more naturally play inside or slot into a back three.

Chilwell is able to adopt central positions well and is at his best when running beyond with dangerous movements to catch defenders off guard in attack, but he looked a long way off being at his peak during the brief sightings during 2023/24. Chelsea are also understood to be targeting a new left-back in the summer window.

Even with Conference League football and injury worries, three does not go well into one, especially not when neither Cucurella nor Chilwell have a natural second position to fill in at. Therefore, it doesn't seem impossible that at least one of them leaves alongside Maatsen.

Chilwell is now entering his fifth year at Stamford Bridge, more than half of which has been spent as a bit-part option or dealing with or recovering from injury. He remains a senior player in the squad, though, and was vice-captain under Pochettino, behind only his fellow injury-troubled England teammate Reece James.

Cucurella has less of a role than Chilwell but is a popular figure at the club. He will cost the Blues £62million in 2022 and is on smaller wages than his counterpart. Chilwell is one of the best-paid players at the club after signing a new contract just over 12 months ago.

Whether there is more value in Chilwell - who Chelsea would now bank an accounting profit on with anything over a £10million sale due to his amortised yearly cost split over the initial contract after a £50million move - or in Cucurella is up for debate. The former is arguably a bigger asset at his best, but Cucurella being available and coming into form at the right time may have something to say.

Either way, it opens Chelsea up to a big dilemma this summer. Maatsen might be gone, but the problems are not.