Paolo Maldini and Ricky Massara to leave AC Milan: What’s going wrong at the Rossoneri?

Things were looking good for AC Milan this time last year, but problems have now come to the surface with Paolo Maldini and Ricky Massara leaving the club. What's going on at the San Siro?


Just days after the 2022/23 Serie A campaign has ended, AC Milan supporters have been rocked by the news that technical director Paolo Maldini and sporting director Ricky Massara will be leaving this summer after being dismissed by the club.

Former Rossoneri captain Maldini is best known for his 25-year playing association with the Milanese giants and lifting the Champions League an astonishing five times during a trophy-laden career, but he returned to the club in an administrative capacity in 2018 and is largely credited with getting the Serie A giants back on track and being influential in their 2021/22 title win.

Massara joined a year later and, alongside the ex-Italian international, helped the club challenge for major honours once more, but The Athletic report that RedBird Capital owner Gerry Cardinale informed them shortly after Milan’s win over Hellas Verona on the season’s final matchday that the club would not follow a new recruitment strategy, which had been desired by Maldini and Massara.

Has Paolo Maldini been a success at AC Milan?

Paolo Maldini and Andriy Shevchenko at San Siro. [@acmilan]

While it took AC Milan a few years to win the Serie A title after Maldini and Massara arrived, the seven-time scudetto winner played an influential role in building the side that coach Stefano Pioli took to the 2021/22 Serie A title, with his standing in the world game enticing several promising young players to the club.

With the 54-year-old back at the club, they secured the signings of Theo Hernandez, Rafael Leao, Fikayo Tomori and Mike Maignan, whilst also having the foresight to understand the benefit elder statesmen can have, such as Olivier Giroud. Maldini was quickly promoted from sporting strategy and development director to his current position within one year.

In 2022, the duo were rightly recognised for their role in that Serie A success when jointly awarded the Sporting Director of the Year award at the Globe Soccer Awards.

Why have Maldini and Massara been sacked by Milan?

Paolo Maldini and Zlatan Ibrahimovic. (@acmilan)

Maldini and Massara have paid the price for the Rossoneri’s miserable attempt to defend their Serie A crown this season, finishing 20 points behind champions Napoli and only just scraping into the Champions League qualification places with the help of Juventus10-point deduction for their capital gains case.

In addition, Milan lost the Champions League semi-final comprehensively to Derby della Madonnina rivals Inter, during two matches that exposed a lack of depth on the Rossoneri bench.

The recruitment policy in place last summer was criticised heavily, as it saw the underperforming Sergino Dest, Yacine Adli, Divock Origi and Charles De Ketelaere arrive.


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