The groundbreaking Tottenham and AC Milan double swap transfer deal that could break the internet
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Rumours suggest that Spurs and AC Milan could be trading several players this summer - but would it pay off for Thomas Frank’s team?
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As Spurs begin the process of reshaping their squad to match new manager Thomas Frank’s requirements, Daniel Levy may soon find an unusual and convoluted deal coming across his table, centred around AC Milan’s apparent interest in two of their players.
A growing number of reports – including one from TBR Football – suggest that Milan are interested in Spurs’ first-choice goalkeeper, Guglielmo Vicario, while other reports from Italy suggest that Milan’s newly-appointed sporting director, Igli Tare, has met with the agent who represents both Vicario and his team-mate Radu Draguşin, with both considered options for the Italian side.
Spurs, for their part, are likely to still hold interest in Milan’s Fikayo Tomori, who rejected a move to the Tottenham Hotspur Stadium in January, and are supposedly “open” to selling Vicario despite his highly impressive performances in his first season with the club. Throw in the fact that Milan’s own goalkeeper, Mike Maignan, is trying to engineer a move away, and a rare double swap deal could be on the cards. It would be complex to negotiate, to say the least, but it might make a certain amount of sense for Spurs.
Would Mike Maignan be an upgrade on Guglielmo Vicario?
As it stands, none of the reports centred on Milan’s interest in Vicario have suggested that Maignan could be used directly as a makeweight, but Milan are happy to sell the 29-year-old Frenchman, and only turned Chelsea’s bid away because they wouldn’t raise it beyond a mere €15m.
Chelsea, for their part, were likely unwilling to part with more because Maignan is coming off the back of a comparatively indifferent season. Although the Frenchman was superb when Milan won the Scudetto in his debut season in Italy in 2021/22 (and arguably even better when winning Ligue 1 with Lille the year before), he has been inconsistent since, with his statistical output never matching that brilliant campaign again.
Still, while he may not still be hitting the heights which saw him widely touted as one of the best goalkeepers in the world, he remains a very fine player who is both extremely comfortable playing well outside of his penalty area but who also offers pinpoint distribution – and who still makes a higher percentage of his saves than Vicario.
Vicario has a handful of rough moments between the sticks as Spurs goalkeeper, but remains capable of the outstanding, and since joining from Empoli has prevented the equivalent of 4.4 goals compared to the xG of the chances he’s faced – Maignan, for his part, has actually conceded 5.4 more than he ‘should’ have, all things being even.
Still, based on the stats, there is a relatively slim difference between Maignan’s ability to keep shots out than Vicario’s, and there are areas of the game in which the Frenchman is clearly better. Vicario is unquestionably stronger at dealing with high balls (he successfully handled nearly 50% more crosses than Maignan over the past year) but Maignan ticks plenty of boxes elsewhere.
Depending on how Frank wants his goalkeeper to operate – how high up the pitch, and how long he wants him to go with his distribution – Maignan could easily represent a tactical upgrade who is similarly strong at making the actual saves. And if Maignan’s circumstances means that Spurs can switch Vicario for Maignan and make a profit, then it could prove to be smart business.
It’s unlikely that Spurs are desperate to get rid of Vicario, and nor should they be. While perhaps not one of the outstanding shot stoppers of the Premier League, he has few weaknesses. Still, a hard-nosed, business-focussed look at the possibility of a profitable piece of horse trading certainly doesn’t suggest that making a change would necessarily be a disastrously bad move.
Is Fikayo Tomori as good as English fans think?
The other half of the equation is a potential deal involving centre-halves Tomori and Draguşin, the latter of which has failed to impress since moving from Serie A to North London himself. Few Spurs fans would be sad to see him go.
They may well be rather happier to welcome Tomori, who is perhaps appreciated more in England than he is in Italy right now. Like Maignan, Tomori was superb during Milan’s title-winning campaign three years ago, but has found it tricky to live up to those performances since.
His positional sense and penchant for a rash challenge have both been a persistent source of criticism, and he was dropped from the starting team for half of the 2024/25 season by former manager Paulo Fonseca, partly due to form and partly due to disobeying his manager’s instructions during a match against Fiorentina to wrestle a penalty from Christian Pulisic so it could be given to Tammy Abraham. The penalty was, perhaps inevitably, saved, and Milan went on to lose 2-1.
Given that his relationship with the manager appeared to be broken after that incident, it was somewhat surprising that Tomori refused Spurs’ overtures during the January transfer window - but perhaps a new head coach and the return of Champions League football will change his mind.
For his part, Tomori did eventually win his place in the team back towards the end of a disappointing season and while he can’t be said to have his best year in Serie A – rather, his very worst – he still has a degree of technical quality that Draguşin has failed to demonstrate in North London. He’s a fine ball-playing defender with an eye for a pass, and Frank may well value that.
Presumably, Tomori would fetch a higher price than Draguşin, although with two years left on his Milan contract and doubts about his future role, the fee may not be too excessive. Given that Spurs need to strengthen the centre of their defence, bringing Tomori back to England would not be the worst chance to take.
There are so many moving parts in the potential dealings between the two clubs that it’s hard to predict the outcome of any negotiations, if they even start in earnest, and more trustworthy media outlets are yet to add their voices to the suggestion that these moves could take place. This could just be speculation rather than a solid transfer story.
But if it does turn out to be the real deal, then perhaps Spurs should give it some serious thought. There’s potential for them to upgrade in two positions ahead of a season in which they’ll be competing on domestic and continental fronts – and perhaps even to add some money to the transfer fund into the bargain.
