AC Milan take on Juventus on Wednesday — 2:30 p.m. ET, stream live on ESPN2 from their perch at the top of the Serie A table, a spot they’ve held since the start of the campaign, or 15 matchdays. The last time they were top for this long was 10 years, seven managers, four directors of football, two owners and a whole load of red ink ago.

Owners Elliott Management took control of the club when previous owner Li Yonghong borrowed roughly $325 million from them, and then didn’t pay it back. They hired former Arsenal CEO Ivan Gazidis and set out to rebuild the club, aiming to return it to what it once was: one of the biggest in world football. With plenty of debt and losses of close to half a billion dollars in the past three seasons, the club’s mantra has been all about trying to win while being smart and turning the books around: buy low (and young), sell high, look for value and keep costs under control.

It’s beginning to work on the pitch as the likes of Ismael Bennacer, Theo Hernandez and Rafael Leao draw rave reviews, but now they have a huge call to make as three key players all become free agents at the end of the 2020-21 season. Gianluigi Donnarumma, Hakan Calhanoglu and Zlatan Ibrahimovic are in the last six months of their contracts, and for the latter pair, as of Jan. 1 they can sign with any club outside Italy for next season.

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It’s an unprecedented situation: league-leading teams don’t let three of their most important players all get within six months of free agency, and yet there are reasons why Milan find themselves in this situation. The fact that Donnarumma (21), Calhanoglu (26) and Ibrahimovic (39) are all at different stages of their careers makes each an interesting case study of the myriad factors a club must weigh up.

Jump to: Donnarumma | Calhanoglu | Ibrahimovic

Gianluigi Donnarumma

Put money to one side and this one is easy. He’s 21 years old, he’s a homegrown player, he’s been the first-choice keeper since he was 16 and an Italy international from the age of 17. He has already made 224 appearances for the club; for context, Paolo Maldini, Milan’s all-time appearances leader, was 23 when he made his 224th appearance. Donnarumma is nowhere near his prime as a keeper, he’s generally unflappable and consistent, and he wants to stay.

A no-brainer, right? Except money does come into it.

In the summer of 2017, when Donnarumma was just 18, the club offered him a monster three-year deal that, at the time, made him the third-highest-paid keeper in the world (he’s now fifth behind David De Gea, Jan Oblak, Ederson and Manuel Neuer). The problem with huge contracts is that, when you extend them, they get bigger and bigger. That’s particularly true when your agent is one Mino Raiola — a guy who is loved by his clients and hated by club bean counters everywhere.

That’s the main reason, incidentally, why Milan were unable to extend his contract earlier. Donnarumma was on huge wages; he was in no rush. And equally, it was difficult for Milan to gauge what sort of budget they might have: they were banned from European football for a season and it was difficult to know how quickly, if at all, they could grow their revenues.

With his client’s contract expiring, Raiola has plenty of leverage. Milan are doing well, Donnarumma is a big part of it and the club would take a massive PR hit if he left for nothing. A lot of goodwill would be lost if they don’t lock him up even if it means paying through the nose.

On the other hand, there are factors working in the club’s favour, too. One, obviously, is that the global pandemic has hit football revenues hard and many clubs have had to tighten purse strings to cope with a projected $4.5 billion loss of revenue across Europe. Another is that one of the few benefits of having a guy on huge money is that very few clubs can afford him, even on a free transfer.

Were Donnarumma to move, you’d expect him to get a raise and earn somewhere north of $20m a season. Only a handful of clubs could afford that, and of those — this is the third pro-Milan factor — very few of them see upgrading their goalkeeper as a priority. You may see him linked to clubs like Paris Saint-Germain or Juventus, and while you can make a strong case he’d be an upgrade over Keylor Navas or Wojciech Szczesny, remember that those guys also have big contracts with years to run, both clubs probably have greater priorities and, like we said, everybody is hurting financially.

So how does this resolve itself? One solution that may work, and that Raiola might try to demand, is an extension with a modest raise and some sort of release fee, a price at which Milan would have to sell. It would need to be a figure that still gives Milan a handsome profit, but is less than what you think Donnarumma might be worth in two or three years’ time when the market has recovered and some of Europe’s big guns might be in the market for a top keeper.

Hakan Calhanoglu

He was named Serie A player of the month for December and the award comes at just the right time for a contract negotiation. Calhanoglu has been a starter since joining Milan in 2017, but it was really only with the arrival of coach Stefano Pioli, halfway through last season, that he began to shine. That goes a long way towards explaining why his contract was allowed to run down.

Equally, once he entered the last year of his deal and continued playing well, the tables turned and he was also in no hurry to put pen to paper. Calhanoglu is Milan’s fifth-highest-paid player, earning in the region of $6m a year. Most would agree that he deserves a bump in wages and, were he to enter the market as a free agent, even with the pandemic, he might easily get $8m annually or more.

But from his perspective, he’s a regular at a big club topping the table of a big league, and that’s by no means assured elsewhere. The perception of Calhanoglu, possibly because he hasn’t played Champions League football or starred in a major international tournament in several years, is that he’s not a game-changer for another top club. He might get an offer from a top club in a top league, but he’d have to fight his way into a starring role.

That’s the carrot Milan can dangle: He can continue to be a key part of the rebirth of a great club. They know he’ll need to get a raise, but he is most definitely not a keep-at-all-costs player. Committing to Calhanoglu means believing you’ll get the version we’ve seen under Pioli, and it also means effectively locking up the attacking central midfield position for several years, possibly putting up a roadblock for a younger player in that role.

Of the three decisions Milan have to make, this is the one that has to, necessarily, be the least based on emotion.

Zlatan Ibrahimovic

This is, obviously, an entirely different case. Ibrahimovic arrived as a Band-Aid with some skepticism a year ago, then played a huge part in Milan’s revival post-lockdown and began 2020-21 in sparkling form. His 2020 numbers speak for themselves: 24 Serie A appearances, 20 goals. On the other hand, he’s Milan’s highest-paid player, he turns 40 in October and he’s been injured since November. Plus, the club have done well in his absence.

The logical thing to do here, for him and for the club, is to sit it out and wait. See if and when he returns to fitness and what you think he can contribute, and then go and figure out whether it’s worth committing nearly one-sixth of your wage bill to him for another season.

It suits Ibrahimovic, too. He was able to return to Milan on his terms because the club were pretty desperate this time last year, and he was worth every penny, not just for what he did on the pitch, but for his leadership and charisma. But that was then. It may well be that come the summer, the club may feel that this team has been fully weaned off Ibrahimovic, his contribution is bound to diminish and he’s worth substantially less. And he himself might feel it’s time to anchor the SS Zlatan elsewhere.