Devil’s Advocate: Prudence and proactivity – Milan’s refreshed stance provides concrete hope for the future

By Oliver Fisher -

The January transfer window feels like it only just ended, but yet speculation never ceases and the rumour mill seldom stops churning regarding what AC Milan are planning for the future.

The hottest topic a fortnight ago was how Milan have decided not to make any notable moves in the January mercato aside from signing 18-year-old striker Marko Lazetic from Red Star Belgrade to replace the outgoing Pietro Pellegri, yet the narrative seems to have quickly chanced.

Winter window

January is the obvious starting point when reflecting upon what we know about the strategy that Milan are in the process of outlining, and many bemoaned the management for their decision to have a quiet month.

Juventus signed Dusan Vlahovic from Fiorentina and Denis Zakaria from Borussia Monchengladbach while Inter got Robin Gosens from Atalanta and Felipe Caicedo from Genoa, so naturally social media into a frenzy given that the Rossoneri are in the middle of a hotly contest battle for both the Scudetto and a place in the Champions League, with their biggest rivals strengthening significantly.

The refereeing catastrophe in Milan’s 2-1 defeat to Spezia and the failure to score against Juve caused some anger around the Milan environment, with the general consensus that something is missing in order to be close to move to the next step.

However, the strategy that Milan deployed was one of patience and prudence rather than desperation. Sven Botman and Renato Sanches were the two names that the club tried for concretely as we have found out since, but the margins were not there to do a deal in January for various reasons.

Rather than signing a player or players who they did not see as being right for their respective roles, they chose instead to try and work ahead of time to bring in the two they really believe will make a difference to the squad in the summer. Milan are working under the constraints of Financial Fair Play, so almost every signing has to be a hit.

January is known as the ‘repair market’ in Italy, and aside from the long-term injury to Simon Kjaer – which saw Pierre Kalulu step up well – the management believe the squad to be in a position to achieve the one main objective for the season: top four.

Is it excited to only sign an 18-year-old striker? No. Is it good for a website like ours to have little to report on, with many links but nothing concrete? Far from it. Despite this, the big-money winter moves for Piatek and Paqueta still haunt and teach us that nothing is a guarantee in reaching that ‘next level’.

Then we turn to sales, and there was almost an equal amount of anger vented at the inability to shift players outside of the project compared to the frustration that no starter-level players came in.

Andrea Conti went to Sampdoria, Milos Kerkez was sold to AZ Alkmaar from the Primavera and Pellegri’s loan was terminated, while Samu Castillejo’s exit failed to bear fruit for a number of reasons.

On the Castillejo front, there seems to have been a common misunderstanding about the player blocking every possible destination. Gianluca Di Marzio told us that he was happy to join Valencia yet they went for Bryan Gil, while Sampdoria emerged as a deadline day option and he wasn’t convinced. He is not solely at fault, nor was it easy to sell either for Paolo Maldini and co. given where the winger’s stock is at the moment.

Just like buying players, selling is difficult too. Firstly there has to be an interested club who are serious about pushing the deal through, then they must agree a fee with the selling club through whatever formula, then the player must green light the move and personal terms must be agreed, all within what might be a very time-sensitive period because the market is so fluid.

On-field resurgence

It must be noted then that any hangover from such a tame January transfer window now seems to have evaporated into thin air, because the cure for it was always going to be success on the field and that has come in abundance.

The first game in February was a 2-1 derby comeback win over Inter where Olivier Giroud showed his tremendous value and all of his experience, which reopened the Scudetto race. A 4-0 hammering of Lazio followed where Giroud, Brahim Diaz, Rafael Leao and Theo Hernandez ran the show, then most recently Leao scored the only goal in a 1-0 win over Sampdoria that sent the Rossoneri back top.

All of a sudden, the question marks surrounding the depth and character of the squad completely flipped to a mantra of belief and the door to the Scudetto race that was hanging open by a thread has been firmly booted back open.

Not only that, but there is a chance to get one over on the neighbours from across the Navigli in the Coppa Italia too and solidify a really good chance at winning a first trophy in over five years.

The old cliche that some managers and directors have used is that players coming back from lengthy injury lay-offs can be like new signings, and at the moment Milan look healthy (touch wood) and deeper than they did going into January, with a less crowded fixture schedule than their rivals too thanks to an absence of European fixtures.

Programming for the future

We can enjoy the current moment and the excitement of a legitimate fight on two fronts, yet it is also important to look ahead because time waits for nobody and also being mindful of the fact Paolo Maldini and Ricky Massara have faced criticism for not being proactive enough.

Starting firstly with the chapter of renewals, there has been a clear change in stance, one which was needed too. Over the summer, many were baffled at how Gianluigi Donnarumma and Hakan Calhanoglu – two assets with a substantial market value regardless of the opinions on them in hindsight – were allowed to walk away without generating a penny in transfer fee.

It was quickly overcome through a blanket acceptable that Maldini was sending a message to agents and players of a hardline stance, that Milan were not going to be pushed around and forced to sign bad contracts any more, and that anyone can be replaced.

Now we have Franck Kessie – who was one of the best midfielders in Italy last season and is only 25 years of age – on his way out while there are doubts over club captain Alessio Romagnoli’s future two. Losing another two key pieces for nothing has forced a complete overhaul in renewal strategy.

Proactivity is the operative word. Head coach Stefano Pioli extended his deal which was always the most important, then Davide Calabria renewed until 2025, Simon Kjaer until 2024, Alexis Saelemaekers until 2026 and Matteo Gabbia until 2026.

The last to commit his long-term future was Theo Hernandez and that was in many ways symbolic, as he netted a big pay rise as a reward for his new-found status as one of the best left-backs in the world, just as Rafael Leao should soon do for becoming arguably the league’s best winger.

Rather than waiting until absolutely necessary to offer players a pay rise, Maldini, Massara and CEO Ivan Gazidis know that working ahead of time to armour core pieces of the project and paying them what they are worth at that very moment is a much more secure and efficient way of future-proofing the project.

Looking into signings for the summer, it seems Milan have clear ideas on what to do in defence and midfield: Sven Botman is the target for the centre-back role and Renato Sanches is the chosen heir to Franck Kessie.

As per Fabrizio Romano and multiple other sources, the Rossoneri leadership are already working through agents to try and get deals agreed for both of them before the window even reopens, which is a good time to link back to the earlier point of trusting in the scouting process and not letting go of the players they 100% believe are right.

Regarding the other positions that obviously need addressing there will no doubt be names that pop up for the striker and winger roles that are being worked on behind closed doors, while it must be remembered that Yacine Adli will be arriving and Tommaso Pobega too will return from loan to play for a spot in the squad.

A well-oiled machine

We conclude with the outline of Milan’s vision which was provided by Gazidis in a recent interview.

“I would still say we are a work in progress. We are still progressing towards where we want to be. But we’re clearly on the right path,” he said.

“And the foundation of that is young players that develop with Milan into world-class talents which then raise the level of the team, which then increases our revenues, which enables us to invest more into the team to be able to retain them.

“If all we do is look back at a glorious past, we’ll be left behind. It’s already happened. It won’t continue to happen. I’m very optimistic about what we’re going to do.”

There is a reason for us all to be optimistic. The club are moving forward on the field and are fighting for trophies for the second season in a row, the mistakes of previous managements are being rectified and strategies are adapting to safeguard the future right now, proactive steps are being taken to improve the squad which feeds into an off-field resurgence where revenues are rising and losses are falling.

Milan fans can step back and look at a very competent squad full of players who care and have further room to grow, a leadership that are quickly learning and an ownership with almost infinite funds to push the boat out when the time is right. The dark days of the mid 2010s suddenly seem so far away.

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