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Manchester United could miss out on another transfer target to Tottenham Hotspur, with reports suggesting that the North London side are preparing a bid for AC Milan forward Rafael Leao.

Although Leao’s contract at San Siro includes a €175 million release clause, AC Milan are reportedly willing to let the 27-year-old Portuguese attacker leave this summer for a reduced fee of around €50-60 million (£43-50 million).

The forward’s time in Italy has not been without controversy, as last season saw concerns raised over his attitude and professionalism. Currently representing Portugal at the World Cup, Leao is said to have had a falling-out with former Milan manager Massimiliano Allegri. While Allegri has since joined Napoli, his successor, Ruben Amorim, is believed to support the club’s decision to sell the player.

According to TEAMtalk, Amorim—who was dismissed by Manchester United in January—has “approved the player’s exit as he begins reshaping the Rossoneri squad ahead of the upcoming season.”

Leao shares several traits with Marcus Rashford; both players excel in similar attacking roles and possess the ability to dismantle defences when in top form. Even Zlatan Ibrahimovic once described Leao as “magical.”

However, Amorim’s 3-4-2-1 formation does not favour traditional left wingers who prefer cutting inside, especially those reluctant to track back defensively. As he demonstrated during his time managing Rashford, the former Sporting CP coach has little patience for players unwilling to contribute off the ball, regardless of their attacking prowess.

Manchester United, under the guidance of INEOS, are reported to be searching for a new left-sided forward this transfer window to replace Rashford, who failed to complete a move to FC Barcelona after the Spanish giants opted to sign Anthony Gordon instead.

Leao has often expressed his ambition to play in the Premier League, calling it a “dream” and naming Manchester United as a club he particularly admires. Despite this, United, Arsenal and Manchester City have yet to make formal offers, even though his representatives reportedly approached all three clubs last month.

This hesitation has opened the door for Tottenham Hotspur, with new manager Roberto De Zerbi eager to strengthen his attacking options on the left flank. The Lilywhites have already spent approximately £185 million this summer, including deals for Sandro Tonali and Mateus Fernandes—both ahead of Manchester United in transfer races—but remain active in the market.

TEAMtalk reports, “Spurs continue to explore options for a left-sided attacker, and while talks are ongoing regarding Manchester City’s Savinho, Leao has now emerged as another marquee target under serious consideration.”

The report further adds, “Leao’s international pedigree, experience, and game-changing ability make him an appealing option as De Zerbi looks to inject proven quality into his frontline. Tottenham’s management are said to be fully backing De Zerbi and the long-term vision he is crafting.”

Manchester United, Arsenal, and FC Barcelona are all believed to be “keeping tabs on the situation” in Milan, hinting that a formal approach could still be made. Should Leao’s price drop late in the transfer window, or if a loan deal with an option to buy becomes available, INEOS might view it as a calculated opportunity worth seizing.

Nonetheless, Tottenham could move decisively, removing yet another player from United’s shortlist. Leao is reportedly “intrigued by the chance to play in the Premier League and would be open to joining Spurs if the opportunity arises.”