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Football London
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Tom Coley

How Chelsea can use previous transfer failure to exploit Milan's Rafael Leao World Cup deadline

In cricket, you can't win a test match inside one session, but you can often lose one. Chelsea are in a similar situation in the transfer market. They have AC Milan in a position whereby the Blues can't sign Rafael Leao before the World Cup, but they can pull the strings and be in a strong position after it.

The 23-year-old was already sought after by Todd Boehly over the summer and had there not already been a £250million transfer spend, his release clause - a sizable £127million - may have been met or at least seriously tested. As it happened, Chelsea probed away with Leao throughout the summer and did what they weren't able to do between March and June, the groundwork.

Having been a frozen asset of Roman Abramovich's, Chelsea couldn't steal any yards on their rivals in the transfer market and started someway behind the opening blocks, and they did it from a walking start too.

READ MORE: Mason Mount sent perfect message to Reece James as Graham Potter's Chelsea prediction comes true

Next summer promises to be different though, and this time Chelsea know that if AC Milan don't act fast to tie down Leao to a longer term deal then the door will be open for them to burst into. The forward, who is on the 30-man shortlist for the Ballon d'Or, has until 2024 on his current deal but would be left approaching sensitive territory if nothing is sorted before the winter World Cup.

Leao will almost certainly be a key player for Portugal in Qatar and will have just weeks remaining before the January window opens before intense speculation and conversations start again. Having allowed Jorginho and N'Golo Kante's contracts to run down over two years and seeing Andreas Christensen and Antonio Rudiger leave on free transfers in the summer, Chelsea know what can happen in this situation.

The contract itself may not put Chelsea off as fellow target Christopher Nkunku signed his own extension over the summer but has a pre-agreement with the Blues, football.london understands. However, it will still be a pressing issue for Milan to solve, and transfer expert Gianluca Di Marzio thinks the World Cup deadline is vital.

Speaking to wettfreunde he said: "I think the only situation that can happen and is interesting to follow is the contract of Leao because Milan has to renew the contract of Leao as soon as possible. Before the World Cup because otherwise one year and a half left until the contract is very dangerous and is a risk for AC Milan.

"It is a risk for AC Milan not to renew the contract of Leao because Leao was and is a target of Chelsea. Of course they wanted the player in the last days of August and they will come back again if he will not renew the contract with AC Milan.

"So the focus of Milan at this moment is only to try to find an agreement with the new agent of Leao and his lawyer and they will do their maximum to renew the contract of Leao. Even if AC Milan in the recent past with the cases of Donnarumma, of Kessie, of Calhanoglu, they decided a price and that's the price. They don’t do exceptions.

"So if they think the contract of Leao should be €6million or €6.5million (£5.2million or £5.6million), that’s the price."

Reports in Italy have suggested that Leao would be willing to sign a new deal at San Siro which does leave Chelsea slightly in a precarious position, but given their attraction to him and that they have recently been in close proximity to the player, it isn't unfeasible to think that he could be persuaded.

Over the summer, technical director Paolo Maldini told Sky Italy: "We have already started talking to him. But not now, for a long time. Every renewal can be simple or complicated, the will of the player makes the difference because that of the club is there.

"Renewal is an issue that we addressed many months ago. Rafa knows that to become stronger than now the solution is to stay with us. We are a young and growing team. He still has to learn many things but we intend to do great things and grow with him. Chelsea’s officially written offer did not arrive but on an informal level it did. Of course, it was rejected."

Di Marzio doesn't think that it is that simple though and it could be a deal that Milan come to regret if they don't get it done soon. "They will not give Leao €10million (£8.6million), €11million (£9.5million) to renew his contract because the philosophy of AC Milan is not to make exceptions but to decide what’s the maximum salary for a player and that’s the offer," he added.

"If the player wants to take this offer and say ok then good. Otherwise they will finish the market."

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