Paolo Maldini and Gerry Cardinale’s names have been side by side in headlines again recently, and not because the former is returning.
MilanNews recall that the most recent exchange between the pair was sparked earlier in the week. The Milan owner – during Monday’s media briefing with selected journalists – called the Rossoneri legend a ‘one-man show’.
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This obviously got back to Maldini, who chose to respond on the sidelines of a Sky event, stating: “It speaks for itself.” This is the most recent chapter in a love story that never truly blossomed between the two, a tense relationship that has endured various stages since May 2022.
From renewal to divorce
There’s a specific date when the two met: 1 June 2022, the day after RedBird Capital took over after Elliott Management agreed to sell a majority stake in Milan. It was the day after Maldini’s interview with La Gazzetta dello Sport, in which he announced he hadn’t yet received a contract renewal offer.
That news was toned down when Cardinale had it leak out from Casa Milan that he wants to continue with Maldini. But the problem was that the new owner wasn’t willing to accept all the demands that Maldini had laid out, financial ones and others to do with operational autonomy above all.
The dispute was resolved on June 30, with Maldini and sporting director Ricky Massara signing their two-year contract extension late that evening. Almost four years later, rewinding the tape makes things clearer, especially in light of the events of recent days.
Over the months, something was beginning to brew in New York, and according to what has been reconstructed, Cardinale’s decision to relieve Maldini of his role at the end of the season was finalised at the end of 2022, then communicated to some members of the management in January 2023.
Meanwhile, the team were struggling in the league after the World Cup break but reached the Champions League semi-final against Inter, where Maldini made some bold statements about investing more to get back to that stage more regularly.
Those words, at the time, were seen as a challenge to Cardinale and his vision for the club. In reality it didn’t matter what he said, as Maldini’s (and Massara’s) fate had already been decided months earlier.
Various disagreements with other members of the management had emerged too, such as with the CEO Giorgio Furlani, as Maldini himself revealed in an interview with La Repubblica.
With the season over and Zlatan Ibrahimovic having bid farewell as a player, Monday 5 June 2023 is the day of reckoning between Cardinale and Maldini. The venue for the meeting was the then Milan headquarters of the RedBird founder, the Portrait Hotel.
Here, in a face-to-face meeting, the definitive separation occurred: Cardinale told Maldini of his dismissal. It was a breakfast that lasted about ten minutes, during which the owner acknowledged Maldini’s status as a living legend, but wanted to emphasise that Milan were and are his property.
Cardinale had even proposed to Maldini the chance to invest in RedBird, but Paolo declined the American’s offer. This refusal, however, apparently had no bearing on Cardinale’s decisions regarding Maldini’s departure from Milan.




Yes already figure it out, Now Milan is only a property not a Champion Club like it was. It all began after Redbird come, fans can only see this Loved Club sinking because some business man that always bragging about strong team in Europe but can’t compete in the league. The problem is clear, to save Milan by got rid Cardinale and his Redbird.
Cardinale is a joke!!! He will eventually sell the club, sooner or later!!! He acting as Owenr but in reality he is just running a hedge fund who ownes the club!! I hope he won’t make long term damage!!! With him we are mediocre team and will never be a serious team!!!
So at the point Cardinale decided to get rid Maldini it was a possibility that he would be firing the architect of a team that became champions of Italy and Europe in consecutive years?
And that still wouldn’t have mattered? What is this guy even doing?
Milan were in the wilderness Before Maldini arrived.
Milan won the Scudetto under his reign, and yet no financial support from Furlani or Cardi.
Cardi sacks him because he believes Maldini is a one man band. Who believes these words from Cardi?
Cardi is only interested in making himself the Golden Boy of the business world, and Milan comes in second.
Milan need Maldini back and Galliani to bring them back to some respectability now!
Ibra is just an ambassador and that’s all he should not choose the next coach.
The constant repetition of Cardinale name alongside Maldini is a perpetual reminder of failure. The public and the media relentlessly criticize the current administration, invoking the “ghost of Maldini” with every setback. The simultaneous appearance of both names in the headlines today isn’t about a “possible comeback,” but rather a “historical reckoning” for the project. Maldini’s desire to preserve the Rossoneri pride is understandable, but clinging to a “glorious past” and refusing to embrace modern financial mechanisms (which now govern clubs worldwide) has sidelined him. The press uses his name as a tool to attack the administration, and he allows it because he hasn’t yet found a project that matches his stature. This makes him appear as a “historical victim” instead of a dynamic decision-maker who develops his economic tools.