The art of selling at the right moment: Milan to face a big conundrum

Nearing the end of the Silvio Berlusconi ownership period after dominating both Italian and European football for the past two decades, the ‘banter era’ truly came into existence as the club spiralled into arguably its longest period of darkness over the course of its proud history.

Die-hard Milanisti will want to cover their eyes before reading out some of these past players: Michael Essien, Cristian Zaccardo, Alessio Cerci, Kevin Constant, Mario Yepes. There are so many more to name, but let’s spare the blushes and embarrassment.

Signing free agents and players well past their prime became a constant theme in the work of former CEO Adriano Galliani. Clearly, that strategy to save costs did nothing but damage the club.

In 2016, Yonghong Li bought the Rossoneri under Chinese ownership, implementing the opposite strategy which led to big-money transfers. It was rash from the very beginning as no real plan was evident from the very beginning in terms of structuring the squad.

Not long after, transfer values would begin to diminish such as Leonardo Bonucci (equalling the club record for the most expensive transfer of €40m) witnessed his stock fall dramatically.

Copying the model of Paris Saint-Germain and buying as many players as possible (only of lesser quality) was deemed another failed strategy.

Yonghong was unable to repay loan instalments and thus Elliott Management – the US-based vulture fund he borrowed from – seized control of the club. Another new era was ushered in, one that quickly saw Milan banned from European competitions for one season after violating Financial Fair Play (FFP) regulations.

They achieved what no previous ownership could accomplish : convincing Paolo Maldini to be part of the project as technical director, aligning the vision of creating success through youth and smart buys, whilst witnessing player values skyrocket over time.

Working alongside former director of football Ricky Massara, Milan all of a sudden regained a sense of identity and self-worth in the way they were handling their business.

As per Transfermarkt, the following signings made since Elliott’s takeover are as follows:

➤ Rafael Leão – Purchased for €34.5m / Current market value of €90m
➤ Theo Hernandez – Purchased for €22.8m / Current market value of €60m
➤ Mike Maignan – Purchased for €15.4m / Current market value of €45m
➤ Fikayo Tomori – Purchased for €31.6m / Current market value of €40m
➤ Malick Thiaw – Purchased for €8.8m / Current market value of €30m
➤ Ismaël Bennacer – Purchased for €17.2m / Current market value of €38m

As you can see, the scouting and networking done behind the scenes to identify raw talent and develop them astronomically should be viewed as a success for the club’s long-term project.

It can be argued that what’s even tougher, however, is knowing the right time to sell your brightest assets at their peak for the best possible price.

Milan has already fallen victim to the expiration of contracts relating to high-performers and regular starters such as Gianluigi Donnarumma, Hakan Çalhanoglu, Alessio Romagnoli and Franck Kessié; all of which drew differing levels of anger from the fanbase.

We understand how the modern game is nowadays. Loyalty is very rare to come by due to the financial standing of some of the best clubs in the world who can afford to splash the cash.

Timing is absolutely everything when it comes to understanding when the most productivity has been exacted from a player and having the sense of awareness and maturity to offload at the right time.

Leão’s name seems to always resurface in these types of debates. The talent is obviously there for all to see and when the Portuguese star is on, he is virtually unplayable with his pace and the seemingly effortless strides he takes with the ball.

Consistency, consistency, consistency. If only that keyword would be a fitting description for the 23-year-old. For as reliable as the team is on him to perform at maximum capacity, that over-reliance is part of the problem for a player who is still yet to prove that he can be reliable every week.

Despite putting pen to paper on a new deal lasting until 2028 with a reported €175m release clause, is it time to ponder whether Leão is worth rejecting big money for?

Well known for his attacking flair and lightning speed down the left-hand side, Theo Hernandez has been an explosive phenomenon partnering Leão. Since his arrival from Real Madrid in the summer of 2019, the Frenchman has contributed a mind-blowing 25 goals and 30 assists to act as a real threat to any opposition defence, good enough to see him transition into a regular starter in the France national team setup.

Besides an inch-perfect cross for Oliver Giroud to head home the winner against Paris Saint-Germain two weeks ago, the 26-year-old has been rather underwhelming by his high standards as of late.

For all of his brilliant work going forward, Hernandez is still vulnerable defensively, especially in one-on-one scenarios. Looking at his discipline record, it’s not good viewing with a total of 47 yellow cards and three red cards accumulated in a little over four seasons at Milan.

Frankly speaking, his childish acts when going to ground after the barest of touches brush his body needs to be stamped out of the full-back’s game in an instant. In the 2-2 draw against Lecce, Hernandez was clutching his leg on the floor after a challenge with minimal contact in the hope of gaining a free-kick. Instead, a goal was conceded at the other end with Milan essentially a man down.

And wouldn’t you know it, Hernandez got straight back up to his feet and continued playing as if nothing happened, except, conceding a costly goal in the process. Yunus Musah copped the full brunt of the blame, but Hernandez has not been pulled up on his antics enough to the point where Stefano Pioli doesn’t want to address the issue.

Would it really be the end of the world if Milan pocketed a hefty fee in the near future?

It certainly felt like the world was coming to a halt when Donnarumma walked out on a free transfer until the signing of Maignan has since proven to be a masterstroke. Yes, some of his saves have been crucial along the way, but should injuries and a potentially high transfer sale be enough to justify a potential sale within the next year or so?

This season, Fikayo Tomori has demonstrated the same level of quality and consistency that made him a household name in his early days under Pioli to hold the defence like glue. Perhaps, he may fancy a move back to England to cement his place in the England team to further convince Gareth Southgate that he is in fact the real deal.

Then there’s the possibility of Bennacer’s reported €50m release clause being triggered, albeit not playing a single competitive match since May. Although the Algerian’s quality in midfield has been sorely lacking which is crying out for some control both on and off the ball, the tough questions will need to be asked.

In order to compete long-term and nail down a long-term project, the depth within the squad will be fundamental when comparing Milan to their rivals both domestically and in European competition.

That said, there comes a time when the financial implications of the game outweigh the talent side of the equation. Of course, selling multiple big names in one window or even letting stars go in consecutive summers would draw scrutiny, threaten the stability of the project and require individual consideration.

Arms were frantically waved in the air after learning about the sale of golden boy Sandro Tonali to Newcastle United for a reported €70m plus bonuses. As the dust settled, and with the way things have worked out since, most didn’t care to bat an eyelid.

It has the feeling of an important 12 months coming up for Cardinale and the Milan management to swallow their pride and make the difficult choices required to consistently compete at the top.

The Rossoneri can ill-afford to make the same costly mistakes.