AC Milan’s Regret Over Enzo Fernández: The €18m Transfer Blunder
Every big club has a transfer that keeps it awake at night. For AC Milan, one of those now wears the captain’s armband at Chelsea and drives Argentina’s midfield on the biggest stage.
Enzo Fernández was almost a Milan player in the summer of 2022. Not a rumour, not a vague idea. A real operation, pushed by Paolo Maldini and Frederic Massara, that reached the brink of completion before collapsing under the weight of clauses, percentages and a tight budget.
A Deal on the Table
Before Benfica turned him into one of Europe’s hottest properties and before Chelsea paid a record fee to bring him to London, Enzo was within touching distance of Milanello.
Maldini and Massara had moved early. They had identified the River Plate midfielder as a priority target, and crucially, they had convinced the player. An agreement with Enzo himself was practically in place. He had given his approval to joining Milan. The sporting project appealed to him, the club’s history spoke for itself, and the path looked clear.
Then the numbers arrived.
River Plate demanded the immediate payment of a clause of around €18m for 75% of his contract, a figure that could have climbed towards €23m. There was another possible structure on the table: €12m plus €8m in bonuses, filtered through intermediaries. On paper, not an outrageous sum for a player of that potential.
But there was a catch that Milan’s hierarchy could not ignore: they would be paying heavily without full control of his rights. For a club carefully managing every euro of its summer budget, that was a red line.
The Turning Point: De Ketelaere Over Enzo
That summer, Milan had already chosen their main bet. Charles De Ketelaere was considered the absolute priority, the crown jewel of their mercato. The Belgian’s arrival required a significant financial effort, and with resources limited, the room for another major outlay narrowed.
Faced with River Plate’s demands and the complications linked to the agency that owned part of Enzo’s rights, the management pulled back. The logic was clear from their perspective: avoid a deal that didn’t guarantee full ownership and instead channel funds into the player they had already placed at the centre of their project.
So Milan stepped aside.
Benfica did not.
Benfica’s Masterstroke, Chelsea’s Jackpot
With Milan out of the race, Enzo moved straight to Lisbon. It took only a few months for him to impose himself as one of the most complete midfielders in Europe. Benfica gave him the platform, and he did the rest.
His performances at club level flowed seamlessly into the World Cup in Qatar. On the biggest stage, he confirmed what Milan’s scouts and management had already seen: a midfielder with personality, range, and the courage to take responsibility when it mattered most.
Chelsea came calling with a €127m offer. Benfica cashed in. The Argentine landed in the Premier League as one of the most expensive midfielders in history. The sliding doors of that 2022 summer window had swung shut on Milan.
From Missed Target to World-Stage Leader
Enzo has not stopped there. At the current World Cup, the 25-year-old has again been central to Argentina’s charge to the final. In the semi-final against England, with the clock ticking down and the pressure suffocating, he stepped up.
Lionel Messi slipped him the decisive ball. Enzo struck the equaliser in the dying minutes. Another decisive moment, another confirmation of a player who thrives where others shrink.
Now his name is linked with Real Madrid, the natural next step in the rumour mill for a midfielder of his stature. His value, both sporting and economic, has gone far beyond any figure Milan once debated in a meeting room.
For the Rossoneri, the story is simple and brutal: in 2022 they balked at €18–23m for 75% of his contract. Two years later, Enzo Fernández is out of sight, out of reach, and firmly filed under the category that no sporting director likes to revisit: the one that got away.
