The ups and downs of Paolo Maldini’s return to AC Milan, and what could be next

When Paolo Maldini was sacked during a meeting with Gerry Cardinal’s company representative, a dep crisis began within AC Milan. An organizational crisis at the beginning of a new era for the club.

Maldini and Frederic Massara were not only directors Milan. They perfectly balanced the relationship between team and ownership, trying to provide a filter for the strong pressure from the media.

Mistakes have been made and there hthere have been many, especially in the last 12 months. AC Milan has burnt its entire transfer budget, worsening the salary income statement without showing any signs of improvement.

With Maldini, a legacy built up as a player and director goes up in smoke. The former CEO has ended his very long and professional relationship with the club, which started as a player and continued as a general manager.

Maldini was an outstanding defender, regarded by many as the best Italian defender of all time. During his career, which spanned 25 years, he only wore the Milan jersey. He won 26 trophies with the club, including seven Scudettos, one Italian Cup, five Italian Super Cups, five Champions Leagues and another Scudetto in his behind-the-scenes role.

The former Milan defender was in the position for five years but was sacked by the club

Maldini protected all Milan players in the media and supported Rafael Leao during two difficult years on the pitch. It is mainly the Portuguese player who is in shock – it was only thanks to Maldini’s stubbornness that the Milan star extended his contract until 2028.

Mail Sports Alvise Cagnazzo looks at what went wrong for the former defender and what could happen to Milan in the post-Maldini era.

DE KETELAERE CASE

After Charles De Ketelaere arrived for more than £34 million, he was set to inherit Brahim Diaz’s role and position on the pitch, but has failed to adapt, on or off the pitch.

The first point against Maldini and Massara was that they had written a check for 90 percent of the budget for De Ketelaere. The Belgian midfielder had a high market value, which froze all other processes initially started, including the move to bring Paulo Dybala to AC Milan – before joining Roma.

De Ketelaere’s value has halved since joining Milan, with a smaller impact than Junior Messias – the player with the least national and international appeal in the Rossoneri midfield.

Maldini, with his choice to invest in Kaka’s possible heir, lost the trust of the entire management team, which slowly led to his resignation.

Charles De Ketelaere has had a rocky start at Milan after arriving for more than £34 million

The Belgian conceded just one assist in over 40 appearances in his debut campaign for the club this season

DONNARUMMA, CALHANOGLU AND KESSIE LOSE WITHOUT EARNING A DIMMER

Hakan Calhanoglu started in Inter Milan’s Champions League final against Manchester City, but was one of the pillars of AC Milan until a few years ago.

Franck Kessie, meanwhile, is the second major regret in Milan’s recent trades – a great technical and tactical player who was never replaced. Even Gianluigi Donnarumma, although successfully replaced by Mike Maignan, could have brought AC Milan a check for at least £43 million if his contract negotiations had been successful.

Maldini defended AC Milan’s history and economic dignity by not renewing those three contracts, but they are now likely to suffer the consequences of not retaining and then immediately reselling the team’s three jewels.

The club found it difficult to keep those players at the time, but the squad is now weaker than it was. The midfield is poor quality and Maldini and Massara are to blame for not being able to replace two of the strongest midfielders in Serie A.

Cardinale has also looked closely at what has happened and has chosen to cut ties with the past, refusing to pay attention or show gratitude to those who brought the club back to Italy’s top flight.

Neither Hakan Calhanoglu (left) nor Franck Kessie were replaced by the club when they left

Gianluigi Donnarumma, meanwhile, was allowed to leave for free and could have asked for a high fee

PIOLI LOSES ALLIES WITHIN THE CLUB

The biggest damage resulting from the decision is that Stefano Pioli will be left without the two points of reference that made him most comfortable at the club.

Pioli will now have to work without the certainty that he has his two biggest allies behind him and will have to try to create chemistry with the new directors right away.

His task will be more difficult, especially with greater responsibilities and especially in the early stages of the new season. Pioli was Maldini’s trusted man, whom he supported on other managers. He paid back support when he won Serie A.

Milan manager Stefano Pioli has now lost two of his greatest allies in Maldini and Massara

REGULAR MISTAKES SOFT THE SQUAD

In terms of other expenses, Milan was practically immobile and unable to move players who were of no use to Pioli.

The latest catastrophic transfer campaign significantly weakened the position of Maldini, who had made some poor choices – evidenced by De Ketelaere’s operation, who finished his first Italian season with just one assist in more than 40 games.

Sergino Dest, Tiemoue Bakayoko, Yacine Adli, Fode Ballo-Toure, Aster Vranckx and Divock Origi destroyed the club’s salary budget without improving the quality of the team.

Differing points of view in the choice of the player further undermined the relationship of trust between the club and Maldini, and these mistakes ended the former defender’s work with more than 500 appearances for Milan.