AC Milan will host Juventus on Sunday night, and there are six players who could have been on the opposite side had things gone differently.
As La Gazzetta dello Sport write, the nature of Italian football and the media coverage of transfers is such that Milan and Juventus often get brought up as contenders for the same players, and there are even those who could have crossed the divide to join a rival. They reconstruct six such cases.
From Thuram to Tomori
In another life, Inter-Milan would have been the Thuram brothers’ derby. In the summer of 2024, Marcus’s little brother Khephren had a chance to become a new AC Milan player, who were looking to bolster their midfield with a physical player.
Geoffrey Moncada endorsed the acquisition, but Milan didn’t make the move, eventually turning to Youssouf Fofana. At that point, Juventus – looking for a replacement for Adrien Rabiot, now in red and black – closed the deal.
Jonathan David has been targeted several times by Milan over the past three years. In the summer of 2023, Milan attempted to bring him on loan after the Mehdi Taremi deal fell through. Ibra, Furlani and Moncada tried again in April 2024, before attention shifted to Zirkzee and Morata.
The third opportunity came in the fall of 2024, with David’s contract with Lille expiring in June. Fonseca wanted to coach him again, but he didn’t know his time in Milan would be shorter than expected. David had many admirers and a significant salary, so the Rossoneri pivoted to Santi Gimenez.
If it weren’t for Sergio Conceiçao, perhaps Fikayo Tomori would be playing in a black-and-white striped shirt today. In the winter of 2024, the Englishman was close to leaving Milan for Juventus, when things weren’t going well under Fonseca.
Juventus were looking for a replacement for Bremer, and Tomori was at the top of the list. Milan had the chance to earn €25m, but selling cornerstones of the 2022 Scudetto to a rival in the Champions League race wouldn’t have been well received. Conceicao arrived, and asked that he stay.
If there’s one player Allegri would take away from Juventus on Sunday night, it would be Andrea Cambiaso. He is a protégé of Max’s: the two have worked together before at Juventus, they know each other and have similar footballing ideas.
Allegri likes him for his versatility, technique and because he’s Italian, which can’t hurt. Aside from Athekame Milan don’t have a natural right-back, and Cambiaso has already been put at the top of Milan’s wish list several times. There’s one problem: his price. A year ago, Man City offered €60m.
Max did reunite with Koni De Winter in October. He watched him grow up at Juve, where KDW played for four years, between the youth team and the second team. Interesting fact: Allegri gave him his debut in the Champions League (against Chelsea and Malmo) but never in Serie A with Juve.
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At Milan, he had a terrible start, playing in the Supercoppa Italiana in December and getting dominated by Rasmus Hojlund, but then he recovered over time, even scoring a goal against Roma at the Olimpico.
Until three months ago, Mike Maignan was set to be a free agent. His future was uncertain, his contract expiring, and Juventus were shadowy, trying to determine the feasibility of a free transfer this summer. Comolli was convinced he could become the Bianconeri’s No.1 goalkeeper for the future.
Nothing concrete ever materialised and ultimately Maignan extended his contract with AC Milan until 2031 at the end of January, quelling all transfer rumours. Milan will have their captain guarding the net again next year.