Milan’s Leao and Maignan are made for magic moments, but can the club hold onto them?

Two sliding doors. Two moments that define a match. Rafael Leao receives the ball well inside his own half and streaking down the pitch, shedding opponents (three of them) along the way before laying it off to Olivier Giroud for the easiest of side-foot finishes. And then Mike Maignan diving low to his right to snuff out Khvicha Kvaratskhelia’s penalty ten minutes from time.

That’s the thing about football. It’s a low-scoring sport and moments — chances taken and chances spurned — carry an outsized importance. You mention those two moments, and there are plenty of others you could call upon from the 180 minutes of the Napoli vs. AC Milan Champions League quarterfinal: Referee Szymon Marciniak (and the video assistant referee) not awarding a penalty when Leao’s foot hit Hirving “Chucky” Lozano before clearing the ball and that a penalty should have been awarded. Giroud himself seeing his penalty saved by Napoli goalkeeper Alex Meret.

I’m sure you can come up with your own inches and millimetres and blinks of an eye that could have turned this quarterfinal tie. But here’s the thing. Football is a team game and you win as a collective. Except, within that collective, it’s individuals who determine outcomes. Or, put differently, guys capable of the extraordinary — like Maignan and Leao — decide games.

In the simplest equation, clubs value players (or, ought to value players) based on two criteria. The first is simple. How often can they achieve the extraordinary? The other is the yin to that yang. Because, yes, it’s a team game and how well you execute the ordinary within the collective framework, without making mistakes, matters a whole heck of a lot too.

How much those two attributes are worth to you as a club are integral to the story of how those players became major contributors to Milan. And, especially in the case of Leao, whose contract expires in June 2024, whether they will remain a part of it. In both cases, major contractual decisions — one by a sports arbitration court ink Switzerland, one by MIlan themselves — led to Leao and Maignan ending up at the club. Both have worked out. Both could have gone badly wrong. And in Leao’s case, there’s another one to come.

Start with Maignan though, because that’s seen as an unqualified success. Two years ago, Milan made a very tough decision, opting to take a hard-line with their incumbent keeper: Gigio Donnarumma. Donnarumma had just turned 22 and was a prodigy who established himself as a starter at the tender age of 16. He looked the sort of generational talent who might spend twenty years between the sticks for the club. And, from their perspective, they needed such a leader, given they were in absolute turmoil: the club’s owner, Li Yonghong, had defaulted on a loan he took out to acquire the club, and Milan passed to his creditors, Elliott Advisers, an American hedge fund with no track record in football.

Donnarumma’s agent, the late Mino Raiola, tried to leverage the situation, as agents do. He had already secured a massive deal for his client three years earlier, one that paid him around $14m a season, making him one of the highest paid teenagers — influencers and pop stars aside — in the world.

Milan were haemorrhaging money — COVID didn’t help — but Raiola felt his client needed a hefty raise to reflect his growth in that time and he gambled that, with free agency a few months away, they’d be under immense pressure to pay him whatever he wanted.

Milan did what clubs should do but often don’t. They attempted to figure out what Donnarumma’s actual value to them was and how much it would cost to find a replacement. They came up with a number — substantially lower than Raiola’s, which reportedly was in the $20 million range — and stuck to it. When Raiola called their bluff, negotiating with other clubs, they walked away and signed his replacement from French club Lille: Maignan. (Donnarumma ended up at Paris St Germain, eventually signing for less than what he was asking Milan.)

Maignan’s transfer fee was around $16m, plus bonuses, and his reported salary is around $5.5m. He has been one of Milan’s outstanding performers, both in terms of consistency and in delivering the extraordinary in big moments, like the Napoli clash (not just the penalty save, but the stops he made late-on in the first leg, to preserve a 1-0 home win).

Leao’s tale is more complicated. Here too, Milan have to make a decision: extend his deal or see him leave in the summer, when he’s likely to negotiate a deal in excess of $100m in transfer fees. Leao undoubtedly does the extraordinary very, very well. His combination of unpredictability, agility and raw speed can make him unplayable. A winger who beats an opponent in a wide area is the equivalent to the old line about “everybody having a plan until they get punched in the face”: it busts open the most disciplined of defensive set-ups. He chips in with goals and assists, often when Milan need them most. And he has that Mbappesque quality of appearing out of nowhere.

On the flipside, he can disappear from games for stretches and his work off the ball isn’t as resolute or disciplined as some critics would like it to be. He turns 24 in June and the sense is he could turn into Thierry Henry or he could end up being Anthony Martial (nice player — when fit — not quite Henry).

Making that assessment — and putting together a “red-line” offer, just as they did with Donnarumma — is tough enough. But there’s a major wrinkle here, a key decision made years before by successive tribunals which complicates matters to no end.

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In May of 2018, when Leao was at Sporting in Portugal, a group of 50 hardcore fans — unhappy with the club’s performances — burst into the club’s training ground and attacked players and staff. He was 18 at the time, had made just three first team appearances and had just signed a contract that paid him a basic salary of $70,000 a year. He and a group of other players filed a motion to have their contracts terminated for “just cause,” citing fears for their safety following the attack and claiming the club’s president at the time, Bruno de Carvalho, had used inflammatory language, effectively inciting the riot.

A Portuguese tribunal found in his favour, granting him free agency and allowing him to join Lille. This set in motion a complicated series of legal events involving Portuguese courts, the Court of Arbitration for Sport in Lausanne and FIFA’s Dispute Resolution Chamber (DRC). (If you’re into sports law, you can read some of the nitty gritty here).

A year later, Lille transferred Leao to Milan, for a fee of around $33 million. In the meantime, Sporting argued that Leao was not entitled to rescind his contract and a court ruled that he needs to pay €16.5m in compensation. That too is under appeal, but for now, Leao had to pay up. And since it’s money he doesn’t have — he currently earns around $2.5m a season — every month a fifth of his pay check is set aside to repay Sporting. (The Portuguese club have also taken legal action to seek compensation from Lille, at a minimum a hefty cut of the profit they made when they transferred him to Milan.)

And this makes Milan’s decision devilishly complex. The money Leao owes Sporting has to come into the equation but to what degree? And, if, say, Leao demands a transfer fee of €100m, can Sporting come back and claim a part of those proceeds, based on the fact that he should never have been allowed to leave their club?

All questions for lawyers and tribunals. All matters that underscore just how important it is to make the right decisions at the right numbers. Maignan and Leao are players who turn games in an instant. They are what transform football games into legitimate contests: otherwise, the better team with the better players would always win. A fan might say that’s priceless. Milan know it has a price. The tricky thing is figuring out just what that price should be.

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