De Zerbi puts Rafael Leao on Tottenham's shortlist after informal talks with AC Milan
Quick summary
Tottenham manager Roberto De Zerbi has added AC Milan winger Rafael Leao to his shortlist following informal contacts with the Serie A club.
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Attributed to original sourceReports in the UK claim that Roberto De Zerbi is hoping to add another left-sided forward to his ranks at Tottenham Hotspur, and that the club have held informal discussions with Milan for Rafael Leao, who is part Spurs’s three-player shortlist.
Leao option for Tottenham after record deal for Tonali Tottenham have made it clear that they are willing to invest heavily in order to avoid a repeat of the 2025-26 season, which almost saw them relegated despite having won the Europa League the year before.
The headline news is that Italy international Sandro Tonali is set to join in a club-record deal worth €116m including bonuses . That is on top of another expensive deal for Mateus Fernandes from West Ham and Jean-Paul van Hecke from Brighton & Hove Albion. The North Londoners have also brought in proven Premier League experience in Andrew Robertson and Marcos Senesi on free transfers.
NEWCASTLE UPON TYNE, ENGLAND – FEBRUARY 24: Sandro Tonali of Newcastle United celebrates scoring his team’s first goal during the UEFA Champions League 2025/26 League Knockout Play-off Second Leg match between Newcastle United FC and Qarabag FK at St James’ Park on February 24, 2026 in Newcastle upon Tyne, England. (Photo by Carl Recine/Getty Images) If Tottenham bring in another starting-quality left winger, the club’s total summer spend could be approaching the €400m (£350m) mark according to reports from the Independent .
The Independent reports that Tottenham and De Zerbi’s preferred option in attack is AFC Bournemouth’s Eli Junior Kroupi, who is said to be valued in the region of €93m (£80m).
MILAN, ITALY – MAY 10: Rafael Leao of AC Milan gestures during the Serie A match between AC Milan and Atalanta BC at Giuseppe Meazza Stadium on May 10, 2026 in Milan, Italy. (Photo by Marco Luzzani/Getty Images) Thursday’s report claims that Tottenham have a shortlist of three players for their left wing position, which also includes Milan’s Leao and Manchester City’s Savinho. The Independent reports that there have been informal discussions regarding Leao between Spurs and Milan.
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What happened
Tottenham have opened informal transfer channels with AC Milan over a possible move for Rafael Leao. The Portuguese winger has been placed on the Spurs shortlist by head coach Roberto De Zerbi, who sees him as a key attacking reinforcement. No formal offer has been reported at this stage, with discussions described as preliminary. Leao remains under contract at Milan but his future has been the subject of recurring speculation in recent windows.
Chance analysis
Leao is a high-value attacking talent whose potential availability would significantly reshape Tottenham's forward line. The informal nature of the talks suggests early-stage exploration rather than imminent action, but De Zerbi's personal endorsement indicates strategic priority. For Milan, losing Leao would be a major sporting and financial blow; for Spurs, securing him would mark a statement signing. Prediction models should weight this as low-probability but high-impact rumor.
If advanced, a Leao deal would significantly strengthen Tottenham's attack while weakening AC Milan's offensive depth and potentially forcing a squad rebuild.
Monitor for progression from informal talks to a formal offer — a confirmed Leao signing would materially upgrade Tottenham's attacking output projections.