MN: Top five most expensive signings made by Maldini and Massara – a new leader

By Oliver Fisher -

Charles De Ketelaere will be the most expensive purchase that AC Milan have made for some time, taking top spot in the ranking of the Paolo Maldini and Ricky Massara era.

MilanNews writes how over their four years as directors, Maldini and Massara have shown that they are willing to invest quite large sums for young and talented players if the owners (Elliott Management) allow them to.

That has continued into this summer, and De Ketelaere will arrive from Club Brugge for €32m plus €3m in potential bonuses which instantly puts the Belgian at the top of the ranking of the most expensive purchases overseen by the current technical and sporting director.

  1. Charles De Ketelaere – €32m + €3m bonuses
  2. Rafael Leao – €29.5m
  3. Fikayo Tomori – €29.3m
  4. Theo Hernandez – €21.5m
  5. Ismael Bennacer – €17.2m

The striking thing about the list above is that the four signings made prior to CDK have all become key parts of the squad, suggesting a ‘sweet spot’ has been found regarding investment.

Tags AC Milan Charles De Ketelaere Fikayo Tomori Ismaël Bennacer Rafael Leao Theo Hernandez


  1. When we bought leao then we also gave them Tiago Djaló who was valued at 4 mil in the deal to lessen the price.

  2. This is how Milan have always done business, and glory hunters don’t understand that, they want us to spend 100m on a player who in the end could be a flop like Maguire, Hazard etc. Shrewd business done by the guys at the top.

  3. I hope this list shows also how important the player is to the club. IF CDK can take the no1 spot amongst these 5, then he’d be the purchase of the decade. 😀

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