Having lost the Coppa Italia final, the time has come for AC Milan to make strong decisions, and one of them will be the head coach position.
As La Gazzetta dello Sport (seen below) writes this morning, Milan can no longer procrastinate. Even if in the last two league games Conceiçao can qualify for a European competition in 2025-26, the management cannot wait any longer.
The rebuild must start with a winning coach and on their list – in addition to Massimiliano Allegri and Gian Piero Gasperini – Vincenzo Italiano’s name has popped up. The Bologna coach has been on the Rossoneri’s notebook for some time, but the way he won the Coppa Italia has ‘enchanted’ Milan.
An answer needed
Milan need a signal to plan a resurgence after a ‘failed season’, as CEO Giorgio Furlani honestly defined it before leaving the Olimpico on Wednesday night. The only way to change direction is to hire a winning coach, who will bring a breath of enthusiasm to a frustrated fan base.
The Curva Sud have announced that they will boycott Sunday’s trip to Rome, and the comments on social media are vitriolic. Milan must win back their trust, and they must also complete the corporate structure with a sporting director of proven ability and experience.
These are the two moves that will have to come in about ten days, a couple of weeks at most, to plan a winning 2025-26 and not start again with a handicap like a few months ago.
Learning Italian(o)
Beyond the reassuring statements about Conceiçao’s future released by the directors in the various pre-match press conferences, Milan have been working on a new coach for some time, at least since mid-February-March, when the team exited the Champions League and lost all their direct clashes in the league.
One of these was at the Stadio Renato Dall’Ara, against Italiano’s Bologna, who has been on the Rossoneri’s radar for some time. The ‘lesson’ given by Bologna on Wednesday night impressed Furlani, Moncada and Ibrahimovic and now the 47-year-old is a ‘strong idea’.
Why is he admired? For the aggressive style he plays, for the work he does on the team, but also for the moral values he highlighted by dedicating the cup victory to the family of former Fiorentina manager Joe Barone.
Transforming the idea into reality will not be easy, however, because Italiano has already spoken about a renewal with Bologna and the will of the parties, especially after the triumph in the Coppa Italia, seems to be to move forward together.
Joey Saputo’s club certainly has no doubts and Giovanni Sartori wants to secure him by extending the current agreement until 2027. At present italiano seems set to stay, but if Milan choose him and raises the level of pressure, will he change his mind?
To get him, the Rossoneri will have to start a negotiation with the Rossoblù and sit down at a table to negotiate, perhaps making the good relationships created during the Tommaso Pobega and Davde Calabria operations count.

Leader of the group
The management have understood that to reverse the negative trend of this season, they need a coach who is followed by everyone for his DNA as a leader and for the results obtained in his career. Not necessarily in terms of trophies lifted.
Italiano – with the three finals reached with Fiorentina, promotion and then salvation with Spezia and the Coppa Italia with Bologna – would have a nice calling card. Even better is Gian Gasperini who lifted last year’s Europa League and consistently brought Atalanta into European competitions.
He has an agreement with La Dea that expires in a year, but it remains to be seen whether it will be respected, extended or ended. Then there is Massimiliano Allegri, the most successful of all, the coach who, together with the six Scudetti celebrated in Italy, knows Milan well.
Max is free and wants to get back in the game with a big team that will allow him to take revenge on Juventus. The Rossoneri could be the right solution. Roberto De Zerbi and Maurizio Sarri, explored in recent weeks, at the moment seem to have lost momentum.
Sporting director
The question of the coach is linked to that of the sporting director who will arrive. After months of casting and the indecision whether or not to add a new figure, the decision seems to have been made.
The idea is to quickly identify a new director, who will be operational on the market and will support the coach in daily life at Milanello. There have been discussions with Fabio Paratici, whose candidacy fell through, and then with Igli Tare.
However, the profiles of Tony D’Amico, Sartori and Giovanni Manna are also liked, even if their respective clubs do not want to let them leave. Milan are reflecting, but will soon take action. There is no time to waste after a failed season.






Well all the news I read, is making the opinion on me, that this Milan is like Real Madrid. There is no room for failure.
To be honest, Milan, since Berlusconi decide to sell this team. Milan is no longer a european giant anymore.
No more a passionate owner for this club. Just ran this club in the point of business only.
So, you can changing coach every year. But, as long the owner have no passion to make Milan great again, its useless.
Even if we hire Maldini again, I still not sure Milan will great again.
The current owner must more care, and more in touch with his club. Make a bonding with the club, and history, and fans.
Seeing Milan right now, is no different to see a mediocre club.
So, yeah, just hoping the best for this team, whoever the coach next season, and whoever the players come in and out.
During Berlusconi’s ~5 last years we were no where near the European giant we had been. The downfall started way before the new owners came into play.
Being Italian is irrelevant. It’s more about Serie A experience and success. That is a plus, but many other aspects need to be considered:
1-Does he have a clear system of play?
2-Does it suit our current squad?
3-Does it provide a pathway to integrate our Primavera/Futuro stars?
4-Will he be supported by the management, will he get the players he wants?
5-Will he be given time?
I don’t have a problem with any of the coaches mentioned but why would Italiano or Gasperini join this current mess when they have functional teams, in a better position than us, and winning trophies?
Sarri and Allegri are solid but don’t seem like long-term solutions. De Zerbi, as a Milan fan, could be tempted despite qualifying for the Champions League with Marseille, provided he is given the time to build the team in his vision. It’ll be interesting to see which direction we go
Touché on so many points bro.
I’d also like to add that I’m a bit afraid that Italiano turns out to be a Motta 2.0 who enjoyed great success in Bologna but not so much with Juventus.
It’s just my theory, but I think it’s current Bologna under Giovanni Sartori who might be good at getting the most out of some players and coaches who might not succeed elsewhere.
Don’t also forget that the pressure in Milan is certainly way bigger than in Bologna.
The one difference between Italiano and Motta is that Italiano is a more proven coach, having success over multiple seasons with Spezia and Fiorentina. You make a very good point though that Bologna seems to have a good support system behind a coach. Something Milan has been lacking the past two seasons.
Maybe they’ll end up making Furlani, Moncada or Zlatan (or all three) the new head coach? After all, their collaboration has been extremely perfect so far and nothing could go wrong with such an approach.
Italiano isn’t ready for Milan. The pressure between coaching Bologna and Milan is night and day.
He needs another stint with Bologna or a jump to Napoli or something…