The separation between Milan and Maldini would arise from the differences in the plans for the new course and for next season in particular.

RedBird evidently wasn't satisfied both with the season's performance, with a fifth place transformed into fourth only by the penalty suffered by Juventus, and with the summer investments, with Charles De Ketelaere and Divock Origi symbols of choices that didn't give results on the field. Flag as a footballer, Maldini returned to Milan in the summer of 2018, nine years after his retirement, assuming the role of strategic development director of the sports area.

In 2019, after Leonardo's resignation, Maldini became head of the technical area. Together with Massara, Maldini built the team that won the Scudetto in the 2021-2022 season, bringing the Italian flag back to San Siro after 11 years and thus winning his first trophy as a manager.

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