Another day, another mess for Milan as Donnarumma nears the exit again

Milan needed this like they needed a hole in the head.

The club are currently seventh in Serie A, albeit 11 points (14, if Roma win their game in hand) away from the Champions League spots. UEFA have yet to rule on whether the club will be granted a "voluntary agreement" enabling them to play in European competition next year without sanction and if they don't get it -- the prospects aren't good -- they will be hit with a settlement agreement, limiting further spending and possibly incurring a fine and other restrictions as well.

Then there's the ownership situation, with the club actively seeking to both find new investors and refinance the monster loan they will need to repay by next October, which I previously covered here. And as if all that wasn't enough, now they're embroiled in another dispute involving their prize asset, 18-year-old goalkeeper Gigio Donnarumma.

Donnarumma's lawyers have written to the club saying the contract extension he signed last summer was done under duress and pressure. Should they take the matter to arbitration (and win), it would mean his current contract would be invalidated and he would become a free agent in June. What's more, it has been further revealed that the release clause -- €70 million ($82.5m) if Milan are in the Champions League, €40m ($47m) if they are not -- negotiated at the time of his extension was never actually registered with the Italian league.

In other words, it can only be described as a "cluster-mess" because a different four-letter word would be inappropriate.

So how did we get here? The tale begins a little more than a year ago.

Donnarumma, who had made his debut at the age of 16 and won his first international cap a few months earlier, was still on his original youth contract, earning around $60,000 a year. Milan were naturally keen to give him a new deal since his was set to expire in June 2018. However, given the uncertainty with the club's situation -- Li Yonghong, who would eventually acquire the club, had paid a deposit but had twice missed deadlines for the balance of what would be a €740m ($850m) purchase -- Donnarumma's agent, Mino Raiola, delayed negotiations knowing that the closer his client crept toward free agency, the more leverage he would have.

Things got so acrimonious that in June (despite the fact that in the meantime, Li had acquired control of the club thanks to a mega-loan from Elliott Management) Raiola went so far as to say that Donnarumma would not be signing a new deal. That led to some fans dubbing him "Dollarumma" and Swedish Milan supporters pelting him with fake dollar bills during the European Under-21 championships.

A month later, in July, a deal was reached as Milan pulled out all the stops to persuade him and his family. Donnarumma signed a four-year contract extension, tying him to the club through 2021. Along the way, he got a nice bump in wages as well, up to a reported figure of around $13m a year (gross). It's probably not a coincidence that they also signed his older brother, Antonio (also a keeper) as a free agent to a deal worth in excess of $2m a year. An appendix to the contract was added, stipulating that the younger Donnarumma was subject to the above-cited release clause.

This is where things get fuzzy, on two separate parts.

The first concerns the clause itself. For reasons on which we can only speculate, it was never registered with the Italian FA, meaning it has no legal validity within Italy. It does have legal standing with FIFA, however, as long as it is countersigned by both parties. And that means that it can be exercised by a foreign club, at least in theory.

In practice, there isn't much jurisprudence on the matter and according to a sports lawyer familiar with such matters, it would be a very complex and uncertain process, particularly since there is no standard wording for such clauses in Italian sporting jurisprudence -- unlike, say, in Spain, where the Neymar deal was rather straightforward -- and we simply don't know what exactly is in it.

According to Italian rules, such clauses must be registered by the club within a set number of days. If this doesn't happen, the player or his representatives can do it. In this case, neither did, perhaps because they figured it was to their advantage.

The second point is that Donnarumma's representatives contacted Milan on multiple occasions beginning in late September. They complained that the club exerted undue pressure on the player and that he was effectively compelled to sign without the required serenity. Milan replied with a statement simply saying that Donnarumma was an important sporting and economic asset with a deal through 2021 and the dialogue with him is always "positive" and "open."

Raiola could appeal to an arbitration tribunal to try and get the contract canceled, at which point Donnarumma would become a free agent in June. According to Fabio Iudica, a law professor and judge at the Court of Arbitration of Sport, who spoke to Corriere della Sera, it would be a long shot because the burden of proof would be on the player and it's difficult to prove. Still, that it's even a possibility does not bode well for Milan.

Having one of your most important players -- and your biggest asset -- threatening to take you to court and accusing you of coercing him into signing a contract is not a good look. Especially at a time when you're doing the rounds, looking for investment and trying to persuade UEFA's Club Financial Control Body that you have a solid plan for the future.

It's not surprising, therefore, that Donnarumma has already been linked with clubs such as Paris St Germain and Real Madrid: teams who could use a gifted young keeper. What strikes you most though is that after what happened last June, he would agree to be put through the wringer by the media and fans once again.

I don't know Donnarumma personally; maybe he is entirely ice-cool and unflappable. Yet given the bile that greeted him back in June, it's hard to imagine wanting to go through that again now and being once more cast as some kind of greedy villain. Fans generally always eventually forgive ... though they don't always forget. But this promises to be a bumpy few months for him, and that's not a good thing for Milan on the pitch.

Then there's the economic aspect. Properly maintained and nurtured, Donnarumma becomes an asset of $100m or more (maybe a lot more) on the balance sheet. That only happens if he's kept happy and that happens with a solid Milan moving in the right direction quickly enough. Right now, we don't have that.

As for Raiola, he's doing what he does. From Zlatan Ibrahimovic to Romelu Lukaku, from Paul Pogba to Marco Verratti, Raiola is a super agent and that means sometimes going to war for your client. There's no sense blaming him or his methods especially since when the shoe is on the other foot and a club needs him to deliver a player or a fee, they're only too happy to have him around.

Milan are paying a price for the protracted takeover and for failing to put pen to paper earlier. So what can they hope for here? Other than a sudden change of heart -- unlikely but not impossible since footballers are strange animals -- the best seems to be a big fee. Why? Because it's in Raiola's interest to not humiliate Milan any further. After all, at some point he may want to do business with them.

The €40m clause (assuming Milan don't make the Champions League) is just a club for leverage for this point. An interested buyer, knowing Donnarumma wants to come, can offer a little more (say, €50-60m) and avoid the pitfalls of FIFA and litigation. That's what Raiola is banking on and that may also be Milan's best-case scenario.

Either way, it's the last thing the club needed right now.