Where are they now? The 7 Milan signings Maldini made in his first season as technical director
Paolo Maldini loves Milan, and Milan loves Paolo Maldini, thus it’s only fitting that their renaissance was in large part thanks to their second-generation hero.
Son of Cesare, the bloodline runs deep at the Rossoneri. After a fantastic and trophy-laden 25-year senior career with Milan, ‘Il Capitano’ returned to his home in 2018 as a sporting strategy development director under new owners Elliott Management, and found himself promoted to technical director just a year later.
By 2022, Milan had won their first Scudetto in a decade. But how important was the groundwork laid by Maldini in his first summer as technical director? We’ve looked back at their seven signings in 2019 and how they’re faring now, with Maldini having been nudged out of the club by new owners RedBird.
Rafael Leao
Undoubtedly the club’s most valuable player some five years on, Leao arrived to Milan under controversial circumstances, with the winger leaving Sporting CP for free a few years earlier to sign for Lille, before his move to Italy.
Leao was ordered to repay Sporting for the move and the disruption reflected in his first season, but he only grew from there. An improvement under Stefano Pioli in 2020-21 was noticeable and by the 2021-22 campaign, suddenly all eyes were on the Portuguese and his mesmerising ability when running past defenders.
Eleven goals and 10 assists doesn’t even do justice for how joyous Leao was as Milan won Serie A. Paulo Fonseca needs to get a tune out of him in order to enjoy any success.
Franck Kessie
Having been on loan at Milan since 2017, the Rossoneri actually had an obligation to purchase Kessie from Atalanta in 2019 – and what an obligation it turned out to be.
By 2019, Kessie was a mainstay in the side and by 2020-21, was one half of one of the most underrated and well-balanced midfield duos in European football. Kessie blossomed into one of the best midfielders in the world during Milan’s Scudetto winning season, but was also out of contract by the end of it.
Off the back of being integral to their Serie A success, the Ivorian signed for Barcelona on a free transfer, but his move to La Liga didn’t work out and after just one season where he made only seven league starts, he moved to Saudi Pro League side Al Ahli, where he remains now aged 27.
Theo Hernandez
Maldini met Hernandez in Ibiza to personally convince him of the project they were building at Milan, and his efforts were rewarded as the Frenchman chose to join the Italian giants from Real Madrid that summer in an £18million deal.
He hit seven goals and three assists in his debut season from left-back, which is impressive enough. But his feats in the time since have blown those stats out of the water. Hernandez then struck up an immense partnership with Leao on the left flank as they won Serie A under Stefano Pioli, but has also proved his worth playing as a centre-back when not bombing forward as a playmaker.
One of the most unique profiles in football, the 26-year-old is quite possibly the best in class, boasting 29 goals and 39 assists for the club. What a signing.
Ismael Bennacer
The other half of that midfield duo we alluded to, Bennacer signed for Milan from Empoli for just £14.5million, quickly proving a bargain as he developed into one of the best deep-lying playmakers in world football by 2021-22.
Injuries have since hampered the Algeria international, who isn’t the most physically robust. A knee injury kept him out of action for the majority of 2023 and a few niggling issues disrupted him in 2023-24, but he’s still at the club and a key cog in the machine when rotated with Ruben Loftus-Cheek and the ever-athletic Tijjani Reijnders.
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Leo Duarte
The first real miss of Maldini’s first window in charge, Milan signed Duarte for €11million/£10.2million from Brazilian side Flamengo. The defender debuted in a 3-1 defeat to Fiorentina and in his first season he made just six appearances, being sidelined for the majority of the campaign due to ankle surgery.
By the time the 2020-21 season came around, Duarte had lost his place to the pairing of Alessio Romagnoli and Simon Kjaer. He left on loan for Istanbul Basaksehir in January 2021 and has been in Turkey ever since, making the move permanent in 2022.
Rade Krunic
Following Bennacer to Milan from Empoli, Krunic endured an injury-hit first season and was never able to blossom into a regular starter, but Stefano Pioli was never afraid to rely on the Bosnian midfielder when he needed to switch things up.
He made 28 Serie A appearances as the Rossoneri lifted the Scudetto in 2021-22 and racked up 139 appearances for the club before leaving to sign for Fenerbahce in Januar 2024. Considering he cost just €8.5million, Krunic proved excellent value for money.
Ante Rebic
Rebic had previously been in Serie A with Fiorentina before returning to Italy to sign for Milan in 2019. The deal was an initial two-year loan which saw Andre Silva head the other way to Eintracht Frankfurt, but was made permanent via an option to buy just one season in.
Injuries disrupted his 2021-22 campaign, but in the season before that he played a vital role in firing the Rossoneri to a top four finish and laid the groundwork for the later success.
He left the club in 2023 as a Scudetto winner, signing for Besiktas, however he is now a free agent at the age of 30, after his contract was terminated.