At the very least, Milan deserve credit for the appointment.
A club drifting through yet another phase of uncertainty, talking openly about rebuilding, has chosen to begin again with Ruben Amorim. It is an ambitious move. It could work brilliantly. It could fail completely. Either outcome feels possible. What matters for now is that Milan have chosen a direction.
The hope is obvious enough: a new cycle, new ideas, a football identity of its own. Lisbon rather than Manchester.
When Milan’s executives introduced Amorim and spoke of having followed him for years, Sporting was almost certainly where it began. Under his guidance, the club found a place in the European conversation that had felt increasingly remote in recent seasons. A side with personality. Three at the back. Build-up from deep. Width everywhere. Five years that became something of a golden period: six trophies, a 71 per cent win rate, long stretches of control.
Before long, the former midfielder had become one of the most coveted young coaches in Europe.
Manchester United was supposed to complete the picture. Instead, he arrived at a club worn down by tension and never escaped it. The decline showed up most clearly in the results, enough to leave Amorim alongside a series of records nobody wanted. Yet his position often appeared secure. Ownership remained committed to the broader idea, convinced the football would eventually justify the turbulence.
The end came only towards the close of 2025, after Amorim publicly demanded the space and authority he believed belonged to the role. That proved harder to absorb than many of the defeats. The separation brought to a close a spell that, financially as much as sporting-wise, had become disastrous.
Milan have chosen to look beyond it.
Set aside the final months in Manchester and Amorim represents almost everything Massimiliano Allegri did not. Experience against possibility. Conservatism against change. One of Serie A’s established figures against a 41-year-old who already carries himself like a veteran.
That is how Amorim arrived here: from Braga’s reserve side to the summit of Portuguese football. His arrival was expected to alter the future of several players who seemed destined to leave. Rafael Leão, apparently, is not among them.
To strengthen the squad, Amorim has looked towards familiar names. Francisco Trincão. Gonçalo Ramos. Neither an easy deal.
What Milan will certainly get is a coach with something to prove. After the past year, that may not be the worst place to start.