Tottenham Hotspur had a chance to sign the AC Milan star player

13 August 2025 - 6:09 am

 

Reporter Graeme Bailey recently revealed in an interview with TBR Football that Tottenham Hotspur had an opportunity to sign AC Milan winger Rafael Leao. Bailey said:

“My understanding is that, theoretically, due to Son Heung-min’s transfer and Maddison’s injury, some middlemen recommended Leao to Tottenham. It was opportunistic, but that’s how some of the world’s biggest deals are made.”

“However, I have spoken to AC Milan and there has been no progress. They do have a new manager, but I heard that, despite Massimiliano Allegri’s recent appointment, he was adamant that Leao would stay.”

Allegri approved the sale of Tijani Reynders, which means he has a say in other major decisions, such as the signing of Dusan Vlahovic, while also retaining players like Pulisic and Leao.

I hear Allegri has told Milan’s top management that he can develop Leao into one of the best strikers in the world. They don’t intend to lose him, and I don’t think Leo has any plans to leave just yet; he’s very excited about Allegri.

Should Tottenham Hotspur manager Thomas Frank sign Leo?

Leo’s pace is enough to cause problems for defenders on the wing. He possesses a keen eye for key passes in attacking areas. He’s an excellent ball-handler and capable of lobs. Leao has dominated the team’s attacking play thanks to his scoring and chance creation.

The Portugal international primarily plays as a left winger, but can also operate as a center forward if needed. However, there are some questions about whether he can maintain his form in the Premier League.

Leao will add more firepower to Tottenham Hotspur manager Thomas Frank’s attack. His ability is more than enough to make him a regular first-team player for the north London club next season.

At 26, Leao is in his prime, making him a player worthy of consideration for Tottenham in this transfer window. Therefore, it would be wise for Frank to sign Leao as soon as possible.

Leo’s Outstanding Performances in Serie A

Leo excelled for AC Milan last season, delivering a string of impressive performances in Serie A. The Portuguese prodigy made 50 appearances for AC Milan last season, scoring 12 goals and providing 13 assists across various competitions.

The 26-year-old averaged 2.56 shots per 90 minutes in Serie A, with a 43.9% accuracy rate. Leo’s distribution of the ball is also excellent, with a 74.2% pass completion rate in Serie A.