MN: Difficult renewal, bitter dismissal - why Maldini and Cardinale's relationship never took off

Gerry Cardinale and Paolo Maldini were mentioned together again after Cardinale, during a media briefing, described Maldini as a “one-man show.” Maldini responded at a Sky event with “It speaks for itself.” Their relationship has been tense since May 2022, when RedBird Capital took over Milan after Elliott Management agreed to sell a majority stake. On 1 June 2022, Maldini said he had not yet received a contract renewal offer. Cardinale later leaked intentions to continue with Maldini, but disagreements emerged over financial terms and operational autonomy. The dispute ended on 30 June 2022 with a two-year extension signed by Maldini and Ricky Massara. Later, Cardinale decided to remove Maldini at season’s end, finalized in late 2022 and communicated to management in January 2023.

"The Milan owner - during Monday's media briefing with selected journalists - called the Rossoneri legend a 'one-man show'. 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."

"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 Cham"

Read at SempreMilan