August 7, 2025

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How Rafael Leao feels about leaving AC Milan after Tottenham offered chance to sign him

TBR Football understands that Rafael Leao is excited by the prospect of working under Massimiliano Allegri at AC Milan, and vice versa.

The Italian coach makes his return to the San Siro after spending almost 11 years away, and there is a sense of excitement again at Milan.

Allegri himself is also eager to work with the Portuguese attacker and has made clear his intention to transform him into one of the best attackers in world football.

Leao has attracted interest from clubs like Arsenal and Tottenham, who were keen to see if he would be available after Milan missed out on European football, but at this stage, he looks set to stay.

Tottenham offered Rafael Leao, but he wants to stay at AC Milan

Tottenham Hotspur have been offered the chance to sign Rafael Leao through intermediaries, but AC Milan insist the winger is going nowhere, TBR Football chief correspondent Graeme Bailey understands.

James Maddison’s injury and Son Heung-min’s departure have left Spurs in desperate need of reinforcements in attack.

Allegri has already dismissed Leao being sold, and now the Italian giants have made it clear that he is going nowhere.

How Rafael Leao feels about leaving AC Milan after Tottenham offered chance  to sign him

Bailey told TBR Football: “My understanding is that intermediaries on the back of Son’s transfer and Maddison’s injury have put Leao to Spurs, in theory. Opportunistic, yes, but that is how some of the biggest deals in the world have come about.

“However, I have spoken to Milan, and nothing is happening. They do have a new manager, but I am told that even though Massimiliano Allegri has just come through the door, he is firm on his stance that Leao stays.

“Allegri signed off on the sale of Tijjani Reijnders, so that meant he could have a say in other big decisions, like going for Dusan Vlahovic, but also keeping the likes of Pulisic and Leao.

“I am told that Allegri has informed Milan’s hierarchy that he can turn Leao into one of the very best forwards in the world. They are not planning on losing him, and I don’t believe Leao has the wish to leave at this point; he is excited by Allegri.”

Tottenham could be in big trouble if Son Heung-min and James Maddison replacements aren’t signed

Tottenham’s options to replace Son and Maddison are continuing to shrink with 26 days remaining in the transfer window.

Both players contributed to a share percentage of goals in North London last season, and losing that many at once could hurt them

The duo ended the campaign, both managing 23 goal contributions across all competitions, and Spurs will need to find a way of replacing that many goals.

Rodrygo is another sensational option for Tottenham, but like with Leao, he is currently reluctant to leave Real Madrid.

A new number ten and left wing must be targeted, with time running out for them to get deals over the line.

Tottenham actually made an 11th-hour enquiry to sign £37m star but he joined Chelsea instead

Chelsea 'miss out on signing Rafael Leao as AC Milan reject £69m offer' |  Daily Mail Online

Tottenham Hotspur and Chelsea share a fierce rivalry in the Premier League.

Fans of the two London clubs have no love for each other, and the derbies between them every season are usually a great watch.

Chelsea have been the more successful club in recent years – not just on the pitch but in the transfer market as well.

That was evident once again in this window, as Chelsea and Tottenham both eyed a move for the same player, and it was the Blues who ended up winning the race.

Photo by Robin Jones/Getty Images

Tottenham made a late enquiry to sign Jorrel Hato before he joined Chelsea

Jorrel Hato has been a popular name in the transfer window over the last two years.

The Dutch defender made a tremendous name for himself at Ajax after bursting onto the scene as a teenager, and he has been developing brilliantly since.

TBR Football revealed that Chelsea beat Arsenal and Liverpool for Hato’s signature this summer after sealing a £37 million (BBC) agreement with Ajax.

AC Milan Confident in Keeping Star Attacker Amid Barcelona, PSG Rumors

However, just before that happened, Tottenham made an enquiry to sign Hato, but it was too late.

That’s according to Ben Jacobs, who said on Last Word On Spurs: “There is a possibility that another left back is looked at.

“For example, nothing came of it, but very soon after Chelsea came formally to the table for Jorrel Hato, Tottenham put in an enquiry to Ajax as well. It didn’t lead to anything, but it shows you that there’s a young profile of left back that Tottenham are prepared to consider.

“So, let’s see if they sort of stick with Ben Davies, knowing that he’s valued on and off the field, or actually, they try and bring in a sort of teenage profile of left back to compete with Destiny Udogie.

“But either way, I don’t think we’re done with the exploration of the left back position.”

 

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