There was a time when AC Milan were the most feared team in Europe, revered not just in Italy but across the continent as they swept all before them in the pursuit of glory. With names like Franco Baresi and Marco van Basten in their line-up, the Rossoneri were envied and unrivalled anywhere in the world.
After the early 1990s, when those Arrigo Sacchi-inspired teams dominated the game, manager Carlo Ancelotti led stars like Kaka, Paolo Maldini and Andrea Pirlo back to the summit. The Champions League triumphs of 2003 and 2007 were the pinnacle of that team, although they would cling on to add the 2011 Serie A title to their bulging trophy cabinet.
Even now that seems like a distant memory, the team torn apart by a combination of age, expired contracts and a desperate need to cut costs. While both Massimiliano Allegri and Clarence Seedorf have seemingly carried the burden of responsibility, the management above them must also be held to account.
Money may well be much tighter than it was when Silvio Berlusconi first arrived, but Milan’s spending on the transfer market has been difficult to understand and often extremely wasteful. Over the following slides is a chronological look at the five worst examples of that profligacy, looking at their worst deals over the last two seasons.