AC Milan’s recent struggles could spell trouble for Chelsea

Sometimes things just don’t fit perfectly.

When AC Milan bought Leonardo Bonucci in the summer, that signing – more than any other in a £150m+ spending spree in the last window – seemed to herald the return of the Rossoneri back to the top of the European game.

It’s no secret that you need money to compete and by getting investment, Milan enabled themselves to do just that, or so it seemed. But this weekend appeared to show just how difficult it is to buy a new squad and compete at the top straight away. And with uncertainty around the club’s future financial footing, Champions League football could be needed next season to justify the new Chinese owners’ long-term investment in the club.

Even after nine games, that’s beginning to look like a remote possibility. Milan sit in 11th place in the fledgling Serie A table, and have lost as many games as they’ve won so far. They’re already nine points off a Champions League spot, let alone the league leaders, Napoli.

Part of the problem, of course, is expectation. After spending so much money, and especially after the signing of Bonucci, one of Juventus’ fabled defenders, it started to look as though a shot at the title would be possible.

Now that they’ve tailed off, the problem is that the defeat have come to top four rivals. Having already lost to Lazio, Roma, Sampdoria and city rivals Inter, that’s four of the top six they’ve dropped points to. Only Napoli and Juventus from the top six have yet to beat Milan. But they’ve yet to play them.

What happens next will be interesting, though, and one to keep an eye on.

Although Milan are a grand old European name, and they will naturally create interest among those who would love to see them back in the Champions League and in European football again, they might also be worth looking out for because of what might happen if they sack their manager, Vincenzo Montella.

Carlo Ancelotti is available. So too, now, is Ronald Koeman, after being sacked from his role as Everton boss. But one name that might well crop up is that of Chelsea boss Antonio Conte.

Potentially homesick, Conte will certainly not manage Chelsea forever, and could be tempted back to his homeland sooner rather than later, especially if he’s given plenty of money to spend.

In Conte’s time as Juventus manager, he was lured to a job where he could take a legendary old club back to the top of the league and back into Europe again, after their demotion to Serie B and subsequent struggles after being promoted again. But despite success in Turin, one of Conte’s criticisms of the club was the fact that he wasn’t given money to spend on players who could be successful in Europe.

If he’s given the opportunity to manage a similar sleeping giant in his homeland, and this time is promised plenty of money to spend, you could see why Conte would jump at the opportunity. And if a chance like that were to crop up in the middle of the season, would he turn it down in favour of staying on only until the end of the season at Chelsea?

Milan’s struggles this season could well leave Chelsea in a bit of a mess soon enough.