Ground- breaking Tottenham and AC Milan double swap transfer deal that could break the internet

As Tottenham Hotspur begin the process of reshaping their squad under newly appointed head coach Thomas Frank, chairman Daniel Levy may soon be presented with a highly unusual and complicated transfer scenario involving Italian giants AC Milan. At the center of this intriguing development are reports of Milan’s growing interest in two of Spurs’ key players — goalkeeper Guglielmo Vicario and defender Radu Drăgușin — which could open the door to a multi-player swap deal rarely seen at this level of the game.

According to multiple reports, including a recent update from TBR Football, Milan are seriously considering a move for Vicario, who impressed during his debut season in the Premier League. Additionally, fresh claims from the Italian media indicate that Milan’s recently appointed sporting director, Igli Tare, has already met with the agent who represents both Vicario and Drăgușin. The implication is clear: both Spurs players are being evaluated as options to reinforce the Milan squad, with Tare eager to reshape the Rossoneri’s defensive and goalkeeping departments.

Interestingly, Tottenham themselves have a lingering interest in Milan centre-back Fikayo Tomori. The England international previously turned down a move to North London during the January transfer window, but circumstances may have shifted. Tomori’s future at the San Siro appears uncertain following a turbulent season in which he lost his starting place under former manager Paulo Fonseca. Spurs are reportedly still keen and may be willing to revisit a deal.

Crucially, this emerging transfer saga gains further complexity due to the situation surrounding Milan’s current No.1, Mike Maignan. The French goalkeeper is actively seeking a new challenge and is believed to be on the market. Chelsea have already had a bid rejected, reportedly unwilling to meet Milan’s valuation after Maignan endured a disappointing season by his own high standards. Although Milan have yet to offer Maignan as part of a direct swap, his availability raises the intriguing possibility of a rare goalkeeper exchange involving him and Vicario.

Despite Maignan’s recent dip in form, his pedigree is undeniable. A standout performer during Milan’s 2021/22 Serie A title-winning campaign and Lille’s Ligue 1 triumph before that, the 29-year-old still boasts exceptional distribution and comfort operating as a sweeper-keeper. Statistically, he has conceded more than expected based on xG models in recent seasons — around 5.4 goals above expected — yet his shot-stopping technique, passing range, and experience still make him a highly attractive option, especially for a manager like Frank who may value a goalkeeper’s role in initiating attacks.

Vicario, by comparison, enjoyed a strong first campaign at Spurs, saving his team an estimated 4.4 goals above expected and establishing himself as a reliable presence between the sticks. He has had occasional shaky moments, but overall he’s been a consistent performer. His dominance in the air, particularly in dealing with crosses, is an area where he statistically outperforms Maignan by a significant margin. However, if Spurs can upgrade tactically and profit financially by bringing in Maignan while allowing Vicario to leave, it’s an option the club may seriously entertain — especially given Levy’s reputation for balancing ambition with shrewd business.

Meanwhile, the defensive component of this potential exchange is just as intriguing. Radu Drăgușin, who only arrived in North London from Genoa in January, has yet to fully convince. While young and promising, his performances have not inspired confidence, and few Spurs fans would mourn his departure should a better alternative become available.

Fikayo Tomori, in contrast, remains a highly regarded figure in English football, despite his recent struggles in Italy. Like Maignan, Tomori played a vital role in Milan’s title-winning season, but consistency and decision-making issues have plagued him since. A controversial incident earlier in the 2024/25 campaign — where he defied his manager’s instructions by insisting on taking a penalty (which was subsequently saved) — reportedly strained his relationship with Fonseca. The fallout saw him benched for several weeks, further fueling speculation about his future.

Even so, Tomori eventually regained his place in the squad toward the end of the season, and his quality as a ball-playing defender with Premier League experience remains attractive. His contract runs until 2027, but Milan’s openness to reshuffle and Tomori’s fluctuating status could make him available for a reasonable fee. From Spurs’ perspective, he could be a valuable asset in bolstering a defence that still lacks depth and proven quality at the top level.

While any swap involving Maignan, Vicario, Tomori, and Drăgușin would be highly complicated — with valuations, wages, and agent fees all posing obstacles — it’s a situation that could develop as all parties seek solutions that suit their respective summer agendas. Tottenham, competing in both the Premier League and Europe next season, must enhance their squad depth and quality across multiple positions. A strategic double-swap, if executed correctly, could provide them with upgrades in goal and defence while potentially even generating some transfer profit.

At present, none of the more trusted UK-based outlets have confirmed that negotiations are underway, so it’s entirely possible this remains speculative chatter. Nevertheless, the logic behind the proposed deals holds water, and there’s enough circumstantial alignment — from Milan’s goalkeeper dilemma to Tomori’s unsettled status — to suggest this is one to watch.

In the end, whether these moves materialize or not will depend on how aggressive Levy and Frank want to be in this rebuild. But if the right balance of player fit, finances, and squad needs align, then a complex, but mutually beneficial, agreement between Tottenham and AC Milan might just be more realistic than it seems.