Tottenham Hotspur are being backed to land a major upgrade to their forward line by signing AC Milan winger Rafael Leao. Reports indicate that the Portugal international has already said yes to moving to north London, as the club looks to solve its long-standing left-wing problem.

Since club legend Son Heung-min departed last summer, Spurs have struggled to find a consistent performer on the left flank. Several players have been tried in that position, including Xavi Simons, Wilson Odobert, Mathys Tel, Richarlison, and Randal Kolo Muani, but none have managed to deliver the required output. Manager Roberto De Zerbi, who took over midway through the 2025/26 season, saw enough in a short seven-game sample to recognize the need for a top-quality winger to play opposite Mohammed Kudus.

Leao, 27, has been a standout performer for AC Milan over the past few seasons, contributing goals and assists from the left wing. However, his form dipped slightly in the 2025/26 campaign, leading to speculation about a potential move. European football expert Andy Brassell has offered his assessment, suggesting that Leao could be a bargain for a Premier League club despite his current dip.

Why Leao fits Tottenham's needs

Brassell described Leao as a player who is not at his peak but still possesses immense talent. 'He's had some stuff going on off the pitch as well – personal stuff that he's had to deal with which is no doubt affected him,' Brassell told a major radio station. 'But even with him playing below potential, the numbers have actually been pretty good.'

The winger's buyout clause is reportedly €175 million, but no club is willing to pay that amount. However, Leao's desire to leave Milan and test himself in the Premier League has brought several English clubs into the picture. Brassell noted that Leao has shown a 'real disinclination to go to Saudi' and wants to stay in Europe and challenge himself at the highest level.

Leao's performance at the World Cup, where he contributed a goal and an assist in limited game time, highlighted his ability to impact matches. He created the winning goal for Goncalo Ramos with a superb cross, demonstrating his quality on the left side. Brassell compared his playing style to Thierry Henry, praising his effortless dribbling, pace, and ability to change direction.

'He never looks like he's busting a blood vessel, but he's completely outpacing others,' Brassell added. 'Working with a coach as intense as Roberto De Zerbi might get the best out of him consistently, which is exactly what he needs at the age of 27 if he's really to become one of the best players in the world.'

The left-wing problem at Tottenham

Since Son's departure, Tottenham have lacked a dynamic presence on the left. De Zerbi has experimented with various options, but none have provided the explosiveness and creativity needed to unlock defenses. Leao's arrival would not only fill that void but also add a different dimension to the attack. His ability to cut inside and shoot or deliver crosses could complement the strengths of Kudus on the right, forming a formidable front line.

Tottenham's interest in Leao is part of a broader summer transfer strategy. The club has already been linked with several other targets, including a potential triple deal to reinforce the midfield and attack. However, Leao remains the priority for the left-wing position, with sources confirming that the player is ready to make the move.

Expert analysis and career context

Leao joined AC Milan from Lille in 2019 and quickly established himself as one of Serie A's most exciting talents. He played a key role in Milan's Scudetto-winning campaign in 2021/22, scoring 11 goals and providing 10 assists. His dribbling skills, acceleration, and directness make him a nightmare for defenders, and he has drawn comparisons to some of the game's greatest wingers.

However, inconsistencies have sometimes frustrated fans and coaches. Off-field issues and injury problems have occasionally disrupted his rhythm. At 27, he is entering his prime years, and a move to the Premier League could be the catalyst he needs to reach his full potential. De Zerbi's attacking philosophy, which emphasizes fluidity and vertical play, seems tailor-made for a player of Leao's attributes.

Brassell believes that the Premier League's pace and counter-attacking opportunities will suit Leao perfectly. 'He's always fighting for the right to counter-attack,' Brassell explained. 'The fluidity of the Premier League and the pace of it really works for him.'

Potential challenges and competition

While Leao has expressed his willingness to join Tottenham, the transfer is not yet complete. Other Premier League clubs, including Manchester United, have also been linked, though reports suggest United have decided against hijacking the deal. Manchester City's Savinho has also been mentioned as an alternative, but Leao is the primary target.

Financial considerations will play a role. Tottenham may need to negotiate a fee lower than the release clause, given Leao's desire to leave and Milan's willingness to sell. The player's camp is reportedly pushing for a move, and De Zerbi's personal involvement could be decisive. If the deal goes through, it would represent a significant statement of intent from Spurs, who are eager to rebuild after a disappointing 2025/26 season where they finished 17th in the Premier League.

Leao's addition would not only solve the left-wing problem but also provide a major boost to the squad's quality. His arrival could also influence other transfer decisions, as Tottenham look to create a balanced and potent attacking unit. With the new season approaching, all eyes are on Daniel Levy and the Tottenham board to see if they can secure this 'huge, huge upgrade' for the attack.

Source:TEAMtalk News