He would no longer find Galliani singing Venditti to him — “Certain loves don’t end, they take immense detours and then return” — but Carlo Ancelotti would certainly reclaim an important piece of his heart. In Milan, as in Rome...
A suggestion? A hypothesis? A truly viable path? Or is it beautiful even just to imagine it? We are in the realm of hundred-million-dollar questions, but the thought is legitimate: now that the stars in the Madrid sky have become dim — practically shown the door by the white-clad crowd, a sad confirmation that gratitude and football most often live on different planets — why not also consider a return to where that heart once beat strongly? A question that can easily be flipped and, in fact, put this way might even seem more realistic: Milan and Roma, why not think about the old friend? Who knows, maybe that's why in Milanello and Trigoria they haven’t yet revealed their cards for next season’s bench.

Ancelotti in Madrid is at the end of a cycle, even though his contract expires next year. The Champions League exit, decidedly brutal for the refined Madrid tastes, has definitively detonated a situation that had already been precarious for a while. The Spaniards want to part way, and so does he, it’s only a matter of finding the most suitable way to do it: leaving is a coach who, in just six seasons, has placed fifteen trophies in Florentino Perez’s cabinet, including three Champions Leagues, one of which was the long-coveted Tenth. In short, the departure must be with style.
And then?
Then a world opens up. One path, not from today, leads to Brazil. The Brazilian national team has been courting him for some time and the World Cup is not that far off. The bench is luxurious, and in fact Ancelotti is not the only candidate: there are also the Portuguese Jorge Jesus and Abel Ferreira. In reality, Carletto hasn’t even closed the door on the most drastic scenario: stopping here, after thirty years on the bench filled with just as many trophies. An outrageous figure.
Or there would be, precisely, that third path that would take him back to Italy, where it all began.
Ancelotti's scenarios... Roma and Milan in the race?
Roma, where he first made a name for himself. Or Milan, where he bought out the entire store. All together, his giallorossonero adventure as a player amounts to something like 387 matches across eight years in the capital (227 games) and five in Milan (160). Successes everywhere, including cornerstone trophies in the respective cabinets such as the ’83 scudetto in Rome, the two European Cups and two Intercontinental Cups in Milan, reaching the top of the world just as, a few years earlier, the visionary Berlusconi had predicted to him and his incredulous teammates. In red and black, the second act as coach retraced the footsteps of the player: once again ahead of everyone in Italy, Europe, and the world.
But Carlo Ancelotti is much more than a coach with an endless trophy case. He is a coach loved by his teams and his directors, a man of moderation in public, and a manager who gets into his players’ heads on the pitch. A coach capable of generating positive microcosms, which Milan and Roma are both hungrily seeking to create a truly clear and ambitious project. Because, obviously, in either city they would welcome him like the Messiah — but it would be a sporting thrill that cuts across all levels of the clubs.
Lights and shadows
Of course, there are plenty of ifs and buts. Ancelotti earns about 10 million euros net per year with Real Madrid, for example. And compared to Real or Brazil, Milan and Roma would be, for him, a sportingly inferior destination. The heart would prevail, the romantic solution, just as he would be the heart of both projects. Certainly, RedBird and the Friedkins will change coaches. Conceição will finish early in June and Ranieri will become senior advisor to the ownership. Benches will be available (and with a turbulent recent past, considering the mid-season sackings of Paulo Fonseca and Ivan Juric). In Milan, he wouldn’t find the Champions League but an environment that is once again shifting back toward Italian identity. In Rome, relaunched ambitions, albeit burdened by financial fair play constraints. Lights and shadows in both places. But definitely not just any places.
He said in the past: "I’ll return to Roma, I’m in debt, it made me enjoy myself." And also: "Milan marked my life, it’s the team of my heart.” Because in the end, it always comes back to that.
Source: La Gazzetta dello Sport
