AC Milan's Regret Over Enzo Fernández's €18m Transfer

Every big club has its ghosts. For AC Milan, one of the most haunting wears blue in London and white and sky blue for his country. His name is Enzo Fernández, and in the summer of 2022 he was close enough to Milanello that the deal felt almost done.

It never happened. Milan chose another path. And the price of that decision keeps rising.

The deal that was there – and then wasn’t

Before Enzo Fernández became a World Cup winner with Argentina, before the record-breaking move to Chelsea and the talk of Real Madrid, he was a 21-year-old at River Plate with Europe circling.

Inside Casa Milan, Paolo Maldini and Frederic Massara had moved early. They identified him, tracked him, and pushed hard. An agreement with the player was essentially in place. Enzo had given his approval to a move. The project was there, the shirt was waiting.

The obstacle was not desire. It was money – and control.

River Plate demanded the immediate payment of a clause of around €18m for 75% of his contract, with the total potentially climbing to €23m. There was also a proposal, via intermediaries, of €12m plus €8m in bonuses. Whichever route Milan took, one thing remained the same: they would not own 100% of his rights.

For a club still walking a tightrope with its summer budget, that was a red flag. The management were reluctant to commit a significant fee without full control of the asset. They stepped back, recalculated, and made a choice.

They put their chips on Charles De Ketelaere instead, judged at the time to be the absolute priority for the attacking project.

From missed opportunity to £100m midfielder

Once Milan pulled out, the road cleared. Enzo didn’t wait around. He went straight to Benfica, a club that has built a modern empire on precisely these kinds of calculated gambles.

It took him only a few months in Lisbon to show Europe what Milan had walked away from. Fernández imposed himself as one of the standout midfielders on the continent: tempo, bite, vision, personality. The kind of all-court midfielder who looks born for Champions League nights.

Then came Qatar. On the biggest stage, he didn’t blink. Enzo played a central role in Argentina’s run, and his stock exploded. Chelsea arrived with a staggering offer, triggering a €127m move that turned River Plate’s clause into a bargain in hindsight and Benfica’s bet into a jackpot.

Milan’s hesitation at €18–23m had become a story retold every time Fernández dictated another big game.

Enzo now: far from Milan’s reach

The regret has only deepened with time. Enzo is again at the heart of Argentina’s midfield, driving them to another World Cup final. At 25, he already looks like the reference point for his national team’s next generation.

His semi-final performance against England underlined it. With Argentina on the brink, he arrived late, found the moment, and buried the equaliser in the dying minutes, teed up by Lionel Messi. It was the kind of cold, decisive contribution that defines elite midfielders.

Now he wears the captain’s armband at Chelsea, a symbol of status as much as leadership. His name is being linked with Real Madrid, the most ruthless judge of world-class talent there is.

For Milan, he is out of sight financially, a player who briefly sat within reach, nodded yes to the idea of San Siro, and then disappeared into a different tier of the market.

Football is full of what-ifs. This one has a number attached to it: €18m for 75% of a contract. Milan walked away. Benfica didn’t. Chelsea paid €127m.

The story is written now. The only question left is how many more times Enzo Fernández will remind Milan what they almost had.