Tottenham are looking to address their left-wing woes ahead of the 2026/27 season.
Putting the disappointment of last season behind them, Tottenham Hotspur have been showing great intent in the summer transfer window.
They have already put their money on the likes of Jan Paul van Hecke, Andrew Robertson, Marcos Senesi, Martin Dubravka and Mateus Fernandes, whilst having agreed a club-record fee with Newcastle United for Sandro Tonali. Spurs do not want to stop there, as Roberto De Zerbi aims for a comprehensive revamp to make the side competitive again in the Premier League.
One position Tottenham are planning to address is on the left of their attack after failing to replace the iconic Son Heung-min following his switch to Los Angeles FC last August. Plus, Wilson Odobert and Xavi Simons are unlikely to play again in 2026 after suffering ACL injuries, leaving Mathys Tel as the only left-wing option currently in the squad.
Recent reports have linked AC Milan star Rafael Leao with a move to Tottenham. The Portuguese international has made it clear that he wants to leave AC Milan after seven long years. The Rossoneri have seemingly taken note of it and revealed their asking price for their winger.
AC Milan want €60-70m for Rafael Leao
According to reliable Italian journalist Gianluca Di Marzio, AC Milan have met with Rafael Leao’s agents and laid out a plan for his possible exit this summer. They want €60-70m to let the 27-year-old leave after a highly frustrating 2025/26 season.
Leao blew hot and cold throughout the campaign, often playing out of position under former boss Max Allegri. This affected his performance levels and brought a notable dip in his productivity, with the Portuguese trickster ending the season with just nine goals and three assists in 29 Serie A appearances.
Despite his stocks falling in the last 12-18 months, Leao remains one of the fearsome wingers across Europe. The Portuguese has proven he is a truly elite winger at Milan, thanks to his mix of pace, directness, dribbling and unpredictability. He can cause innumerable problems for the full-backs and create chances in the box for strikers.
Due to his ability to go both ways, the Milan winger is always a tricky customer to handle for a full-back. One of the biggest plus points Leao has is his ability to dribble and carry the ball for long distances. Also, the former Lille talent’s proven pedigree at the highest level cannot be ignored.
At 27, Leao is entering the prime stages of his career, and a tactician like De Zerbi could help him regain his mojo. With Milan wanting in the €60-70m bracket, signing the Almada-born talent is a no-brainer for Tottenham.