Chelsea’s baffling Mike Maignan mistake will haunt them for years to come

Chelsea have been made to look like fools by AC Milan and Mike Maignan.

After a lengthy contract saga, the France international now looks set to extend his deal at the San Siro and end any speculation over his future. For the past 12 months, rumours over Maignan’s next move have been rampant.

His current terms expire in the summer, which has naturally attracted the attention of suitors. Last summer, Chelsea attempted to exploit his contract situation and the belief that the 30-year-old was unwilling to stay at AC Milan.

The Blues explored a move ahead of the Club World Cup in June and attempted to lowball the Rossoneri, who reportedly wanted to receive at least €30 million for the world-class goalkeeper.

Chelsea, however, tried to be shrewd negotiators – and it backfired. After two minuscule bids, the second of which clocked in at just half of Milan’s valuation, they left the discussions because they felt they were wasting their time.

Chelsea left to rue Maignan mistake

Maignan was believed to be keen on the move and agreed terms with Chelsea, but he ultimately did not get his transfer. The West London club later briefed journalists that they still trusted Robert Sanchez, Filip Jorgensen and their other goalkeeper options.

Their actions, of course, told a different story. There was a clear – and justified – belief at Stamford Bridge that Maignan would have been an upgrade on Sanchez. Since leaving the talks in June, Chelsea have refrained from making a new move for him.

This has allowed Milan to reach an agreement over a surprise extension, something that seemed unthinkable – at least according to reports – just a few weeks ago. If a move to Chelsea wasn’t completely out of the question before, it most certainly is now.

Chelsea continue to insists that Sanchez is good enough to be their No.1 and they have high hopes for Belgian youngster Mike Penders, who is currently on loan at sister club Strasbourg.

However, until Penders actually steps on the pitch for Chelsea and shows that he can cope with the pressure, doubts will continue to linger. With Maignan, those doubts would never have existed in the first place.

To be sure, the Frenchman did not have a great season last term. But that was very much an aberration, as he is showing in 2025/26. Maignan has been nothing short of sensational for Milan this campaign.

He produced yet another standout performance for the Serie A giants in a crunch clash with AS Roma on Sunday. Milan were not at the races in the first half, but they were bailed out by their goalkeeper, who made numerous world-class saves to keep his side in the game.

Roma had seven shots on target, but it was only a second-half penalty that actually managed to beat Maignan. He guessed the correct corner, but it was too well-placed to be saved.

Maignan is one of the main reasons why Milan are still in the Serie A title race. He has had numerous game-changing performances this season and is showing that he is worth every penny of the bumper new deal he is in line to receive.

He is exactly the kind of big-game goalkeeper Chelsea have lacked since Thibaut Courtois left. Sanchez, though improved this term, is simply not at the same level and he continues to make baffling decisions – like almost running out his box with ball in hand against Crystal Palace.

If Chelsea continue to falter in Premier League title races in the coming seasons, their decision not to spend a little more to bring in Maignan will have been a massive contributing factor.

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