Success, mistakes, aura and the future: Reflecting on Maldini’s time at Milan

A couple of weeks have gone by since the sacking of Paolo Maldini and Ricky Massara, plus the anger and emotions that came with it.

Many Milan fans saw this decision as a huge shock, but now that the waters have calmed down a bit it feels like the right time to properly assess if the decision was a good idea and how this will impact the club moving forward.

For starters, it needs to be said Maldini was, is, and always will be AC Milan. Nobody can represent the club better than him. Not many possess the aura he does and almost everyone will be grateful for the job he has done.

Early days

Maldini was one of the main protagonists behind the rebirth of the club when he first rejoined the club in August 2018 to be part of the management team, shortly after Elliot Management took ownership of the club.

Initially, he was appointed as a sporting strategy and development director, and he worked alongside Leonardo who at the time was the sporting director. The pair worked together in the transfer market with the latter having more power in making the final decisions.

Following the department of Leonardo, Maldini got promoted to technical director and formed a team with Massara and chief scout Geoffrey Moncada which got to be known as ‘MMM’.

The three was in charge of improving the squad along with the vision the owners had: to focus on youth and make the squad more competitive while making smart investments.

This worked well as during his first summer as technical director,  as Paolo signed the likes of Theo Hernandez, Rafael Leao, Ismael Bennacer and Rade Krunic, players that have become integral parts of the squad and who’s value has more than tripled.

Image: acmilan.com

More smart additions were made following this as Fikayo Tomori, Pierre Kalulu, Sandro Tonali, Mike Magnian and Malick Thiaw joined the club on some very good deals and without having to ‘break the bank’ when dealing with the contract negotiations too.

This new approach in the transfer market turned out to be great as this allowed the club to become competitive again, reaching the Champions League after almost 10 years, wining the Scudetto after a decade and even reaching the semi-finals of the UCL.

All of this came while taking great strides forward from financial point of view which made the Rossoneri healthy again after the disastrous reign of Yonghong Li, which resulted in European exclusion and a Settlement Agreement with UEFA.

The aura at work

Of course, Maldini is not the only reason behind this success as everyone played a big part but his part in dealing with the negotiation process and how he spoke for the club to the media and fans was instrumental.

Many of the players who signed during the Maldini era also expressed to the media how talking to Maldini made their decisions to join the club so much easier.

“He called me because he wanted to see me, he surprised me, and it was a very nice meeting,” Theo Hernandez said, reflecting on his arrival at the club.

“He said I had talent, that I could become a great player. We talked about my situation at Madrid, my years at Alavés, at Real Sociedad. We did it as if we were two friends.”

Rafael Leao said similar: “Milan revealed their interest in me. When Maldini calls you, I couldn’t refuse. And I took up the challenge.”

These are just two examples showcasing how great Paolo was from a ‘human’ perspective. Other than his huge image as a player which has earned him respect in the entire footballing world, he possessed a certain charisma that many appreciated.

This is something that helped him build a relationship with the entire Milan squad and was also a big reason behind the ‘family’ type relationship within the squad that has been created over these past three years.

Maldini has been ever present from his first day at the job, from daily appearances at Milanello to stay close to the team to being present at every game and suffering/celebrating along with the rest of us.

It is rare for a football club to have a legend of this calibre this involved with it and for sure something that has been very helpful in terms of growth within a relatively young squad. 

The close relationship of Maldini with the entire Milan environment was showcased the moment he was sacked as the entire fan base rioted online and most of the players posted a picture with Maldini on their personal social media account in a way to show their support to him.

As previously mentioned, it is a decision that in the moment caused a lot of controversy and had the entire fan based worried, but with things calming down now we can evaluate the pros and cons.

Cons

As mentioned, Maldini always knew the right thing to say, whether that was to the fans or the media. He represented the club in a very respectful way and his name alone gave a very strong credibility to the club. This for sure will be missed and something that will be very hard to replace.

This also applies for the negotiation process as, although it is Moncada who has found most of these players, it is Maldini who done the second step which was to convince the players of the project. It will be hard for Milan to find someone who will be able to do this better than how Paolo did.

The presence of Maldini around the squad is another thing that will be missed massively, he built a very strong bond with each player, with Theo Hernandez in particular.

With Maldini gone, this again will be a massive void within the squad and players will miss an important role they saw on a day-to-day basis over these past few years. It makes it even worse knowing they lost him along with another important figure in Ibrahimovic in one go.

Finally, Paolo made it clear in numerous interviews how he wanted serios investment into the squad. He had the right intentions and all he wanted was for the club to be back to where it belongs.

This ‘vision’ will obviously be missed as with the new people in charge, Milan fans are not too sure what exactly they are trying to achieve. With Paolo at least that was clear as his intentions was only to make the club successful on the pitch.

Pros

One way to look at it is that Milan can now move forward with a unified vision. Previously – given Maldini and the owners had different views – it affected the club.

A clear example of this was in the summer of 2022 in which a month was wasted in Maldini negotiating his contract and that costed the club some important players in the market that seemed done (Sven Botman and Renato Sanches). 

As big Maldini is nothing and nobody comes before AC Milan. The new owner’s intentions are not clear yet but it is good that we are all moving towards one direction and no longer wasting more time when the focus should be the transfer window and how to improve the squad rather than anything else.

Secondly, although Maldini played a huge role in some very successful transfers, with 90% of the singings during his time at the club being a huge success, he was not the guy who scouted most of these players.

The person who deserves the merit for this is Moncada, the guy who has taken over Maldini’s role now. Moncada has been working behind the scenes, but his work this past three years should not be overlooked.

He is the man who found so many names that are famous now, but nobody knew about less than two years ago like Kalulu, Thiaw, Leao, Bennacer, Theo and many more.

Moncada also discovered other names that are gone onto do amazing things elsewhere like Enzo Fernandez and Julian Alvarez at Manchester City, who were offered to Milan before anyone else through him, but the management decided to overlook them. 

Maldini’s role in acquiring these players was fundamental as he is the one who dealt with the hiring process, but it is Moncada who followed the lower leagues to find these gems.

By giving him more responsibilities in the market, this can be a blessing in disguise as Moncada is known to find gems that are not worth a lot of money, something that is in line with the vision of the ownership and how the club has been operating.

Finally, this point kind of goes with the previous one but Maldini made some mistakes in the market.

He is not to be blamed as making a mistake is human and it will not overlook all the good work he done, but he did opt to go for Divock Origi instead of Randal Kolo Muani (who Moncada recommended) and for the same wages he offered Divock Origi he could have had Paulo Dybala.

He also failed to sell players and allowed the likes of Kessie and Donnarumma to leave on a free. These players could have brought in some good funds that could have been used to improve the squad.

Paolo also decided to renew Pioli in the middle of the season and then few months later rumours emerged that he was thinking of replacing Pioli.

As said, some mistakes that could have been avoidable, but they were made and the ownership was not happy with which is understandable to why they decided to sack him and hopefully the new management will not make these kind of mistakes which would benefit the club.

What comes next?

So, with the pros and cons mentioned about the decision to sack Maldini, what should the Milan fanbase expect from the updated management moving forward?

For starters, giving more freedom to Moncada is not a bad idea at all, he has proven multiple times that he has a great eye for talent.

It is yet to be seen what the transfer strategy will be like but with this issue with the management resolved very soon, hopefully the new guys in charge can get to work without wasting any time. The next few weeks will give a better clarity to the fans, but we need to stay optimistic and trust Moncada.

Secondly, with Maldini gone and the void he has left, another personality is needed. Someone who represents Milan. Someone who can be close to the team but at the same time speak out for the club well to the media and maintain a relationship with the fans, things Maldini done well.

Lots of rumours have emerged that the new management are trying to get Zlatan Ibrahimovic in for this role, but it is looking unlikely that the Swede is willing to take on this offer, partly because he has just taken a break from football and partly because he probably feels he owes some loyalty to Maldini.

So, although Ibrahimovic would be the best person to replace Maldini as he knew the squad really well, as it is looking unlikely, the second-best option might be Clarence Seedorf.

The Dutchman is one of the most underrated footballers in the history of the game. He was great for the club, won multiple titles and really represented the badge and the No.10 shirt well.

He had an underwhelming stint as head coach few years ago but for someone to stay close to the team and maintain a relationship with the fan base he would be great at.

He can speak 6 languages and is still very much loved by the supporters. His son Denzel is also in the youth sector of the Rossoneri, something that would probably make it easier to convince him to take over the role.

This is how things are looking now, more clarity will come out within the next few weeks. As sad it is to see Maldini leave and as grateful we are for the work he has done, nobody is bigger than the club so us fans need to look forward and hope for a better future with a streamlined project.