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AC Milan forcing Tottenham fans to rethink everything about Rafael Leao

Colombia v Portugal: Group K - FIFA World Cup 2026
Colombia v Portugal: Group K - FIFA World Cup 2026 | MB Media/GettyImages

Portuguese international Rafael Leao is one of the biggest attacking names available in the summer 2026 transfer market, and Tottenham Hotspur have been among the clubs linked to a player who has long been deemed a dream target for clubs in need of a dynamic, goal scoring right footed left winger - and these are clubs as big as Arsenal, Chelsea, Manchester City, and even Barcelona.

Leao has been a disappointment for AC Milan in recent seasons, but, well, Milan have been an even bigger disappointment to themselves, hiring some of the worst coaches in the world and still paying for their 2023 decision to part ways with Paolo Maldini and Sandro Tonali.

The left winger won the Scudetto in 2021/22 and was the MVP of Serie A, and at his best, he is one of the biggest weapons in world football. Big clubs in the Premier League are hoping that they can be the ones to bring that out of him again, and he is seen as one of the biggest gambles available this summer.

Rafael Leao looks better for Spurs now

But he may not be such an expensive gamble after all. Many assumed Rafael Leao would cost 80-100 million euros this summer transfer window, but top Italian transfer insider Gianluca Di Marzio reports that AC Milan's current valuation of the forward is between 60 and 70 million euros, which is a pretty palatable gamble for Tottenham Hotspur and others.

Tottenham just spent a lot more than that on his former teammate Sandro Tonali in the middle of the park, as well as compatriot Mateus Fernandes from rivals West Ham United. So Spurs could very well land a world class left winger who can add 10-20 Premier League goals in a season - and potentially outscore their players from the last two seasons - for a reasonable price.

Leao, again, is not without risk. He has a bit of an injury history, and there are consistency and attitude questions. But given how he has been treated by the Italian media and even his own coaches, namely Paulo Fonseca and Max Allegri, it's hard to fault him entirely for the attitude stuff.

Tottenham have a very charismatic coach in Roberto De Zerbi who coached in Serie A at the same time that Leao was on the rise in Milano, and he is a guy who relishes working with explosive attacking talents. Leao is, at 60-70 million euros, suddenly looking very appealing to Spurs.

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