GdS: Maldini’s infatuation and multiple attempts – the sliding doors for Zaniolo and Milan

Nicolò Zaniolo will hope to score against AC Milan tonight, but there was a time in the not too distant past when he could have donned the red and black.

As La Gazzetta dello Sport write, seeing Christian Pulisic play for Milan might fill Zaniolo with a bit of envy. It was Milan that the Italian saw as the ideal place to be reborn and rediscover himself, but his career took a different turn and he ended up as an opponent.

The background

Zaniolo was regularly linked with Milan. Both Paolo Maldini and Ricky Massara were great admirers, and every transfer window stories surfaced. The first time was in the summer of 2022, when Nicolò was the preferred option should the Charles De Ketelaere deal fall through.

In fact, the Rossoneri management had even made moves in the spring. The player would have been happy to sign, but the demands of his then-club Roma made Milan hesitate, and in the end nothing came of it.

A couple of secret meetings could have unlocked everything. First between Maldini, Massara and Zaniolo’s entourage, then with Nicolò. The player for his part was flatted by Maldini being interested, and by the idea of working with Stefano Pioli.

In January 2023 came the second act. Nicolò was going through a difficult period in the capital and was eager to move to the Rossoneri. Maldini and Massara tried to start negotiations: first in secret, then through discussions with Roma.

The Rossoneri had even created a specific program for him. The goal was to get him back to fitness as quickly as possible and maximise his performance towards the end of the season. The ideas were clear, and Zaniolo was enthusiastic about them.

He was also enthusiastic about the role he would play in Pioli’s system, which had the attacking midfielder position. The coach was crazy about him, as was the management. In short, all the ingredients for a happy ending were there, because Milan and Zaniolo had chosen each other.

There was a romantic element to things too. Kaká had always been his idol, Zlatan Ibrahimovic a role model. After the 2022 UEFA Europa Conference League final – in which Zaniolo scored the winner – Juventus, Napoli, and Milan knocked on the door.

The Rossoneri immediately became his first choice and the playmaker told his agents about this, but again nothing came of it. Not in January 2022, nor six months later. Roma always asked for a lot of money – around €25-30m – without ever appearing particularly open to discounts.

Maldini, moreover, would have signed him after his experience at Galatasaray, but his departure from Milan nipped the idea in the bud. Then, in June, the Rossoneri signed Pulisic, in that role that in another life would have been tailor-made for Zaniolo.

Who knows how it would have gone. Nicolò will surely think about it on Saturday night, watching the team where he could have tried to revive his career.