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AC Milan's losses to Inter in the 2022-23 Champions League semifinals were some of the most disappointing days in the recent history of the club, and they have increased the doubts as to whether the current project led by coach Stefano Pioli can lead this team back to continental supremacy. The European elimination and the disappointing Serie A campaign might change the plans of the Italian club, but that should not compromise the work done in the past three years. 

It's certain that some mistakes were made last summer, but the new cycle that started in the summer of 2019 with Paolo Maldini as the head of the sporting area of the club must be judged in a positive way overall, especially with the Scudetto title won last season. Maldini was able to bring players that only a few considered before, such as right back Theo Hernandez or striker Olivier Giroud, who left Premier League soccer to join the Italian league and flourished.

When Pioli was appointed in 2019 after the sacking of Marco Giampaolo, the Italian manager was considered a caretaker coach until the end of the season, especially after the first disappointing results. Then everything changed when the COVID-19 outbreak stopped Serie A for three months. AC Milan's CEO, Ivan Gazidis, had approached Ralf Rangnick and they had actually reached an agreement to work together. Rangnick wanted a real revolution with younger players and his role was supposed to be coach and sporting director at the same time. Not only would that have ended Pioli's time at the club, but also the working relationship with club legend Maldini. 

During those months, Pioli was helped, especially by the most experienced players such as Simon Kjaer and Zlatan Ibrahimovic, who came back to the club the winter before. That was the secret of that team, that started to create the base of the success that came two years later. In his first full season in charge, after Gazidis changed his mind and kept the Italian coach and club's director, the Rossoneri finally qualified for the Champions League, despite city rivals Inter winning the Serie A title under Antonio Conte. 

At the end of the season, goalkeeper Gianluigi Donnarumma left for PSG on a free transfer and that seemed like a bad signal for the project, but Maldini and sporting director Ricky Massara found a way to replace him with a goalkeeper that only few knew before, Mike Maignan. The French goalkeeper became one of the best in his role in the following seasons and was crucial during the 2021-22 season when AC Milan won the Scudetto eleven years since last time, beating the same Inter on the last matchday of the season. 

This season things didn't go as well. AC Milan are fighting to the end to get into the top four, lost the Supercoppa 3-0 against Inter in January and were knocked out by Torino in the Coppa Italia, before losing the Champions League semifinals. However, before losing to Inter, the European journey was incredibly successful, going through the group stage with Chelsea, RB Salzburg and Dinamo Zagreb, knocking out Conte's Tottenham in the round of 16 and Serie A champs Napoli in the quarterfinals. However, the semifinals against Inter will shape the final judgment of the whole European season, as AC Milan were dominated by Simone Inzaghi's team, especially in the first game played in front of the Rossoneri fans. 

In the last four games played between the two teams, Inter scored seven goals and most importantly conceded zero against AC Milan, showing all the flaws of the side coached by Pioli. The same Maldini spoke about it to Sky Italy in the post-match interview after the second leg loss.

"The gap is real. It's Inter's way of playing that bothers us and we're unable to find countermeasures, then we've struggled even against teams less strong than Inter in the last month," Maldini said. 

AC Milan went through some changes of ownership in the past years and have found some stability, but more is needed. The Elliott Management Corporation (former owners) took over the Italian club in the spring 2018 after Chinese owner Yonghong Li faced financial challenges forcing control to change hands. In the summer of 2022, American private investment firm RedBird Capital acquired the club, and the firm's founder, Gerry Cardinale, became the new owner. Despite all the initial expectations among the fans, the project of the new owners remained the same as before, and the club confirmed Maldini and Pioli would remain, with the idea to continue what they have done before so well. 

Maldini kept his way of working, looking to make smart transfers to build. 

 "Charles De Ketelaere is an example of players who need to grow, that's normal. It would have been much easier and much cheaper for us to go to a player like Paulo Dybala at the beginning of the season, but would he have been the right player for our project? Would he have been appropriate and shared by our owners? No. We have an idea and want to build a young and talented team," Maldini said "It is risky to sign young players. Sandro [Tonali] struggled in his first season. The same happened with Charles this year. But this is our idea of football, our idea of investment. It's a shared view with the owners. If I wanted a stronger lineup I would have made different choices in the market. We have a project which we are developing together. It takes time, knowing that we are AC Milan. Who better our great history better than me?" 

AC Milan opted to sign De Ketelaere for more than €30 million in the summer, while the club signed former Liverpool striker Divock Origi as a free agent, instead of looking for another backup number nine. Giroud was a key player last season when he was considered the replacement for Ibrahimovic, who missed the second part of the 2021-21 season due to injuries. Giroud was one of the main secrets of Pioli's success, but this season he had to play 44 games until now, without a real backup striker that could support him when needed. Not buying a new starting striker was probably the biggest mistake made by the club in the summer. Meanwhile, Ibrahimovic, who extended his deal until the summer 2023, only played four games this season and scored just one goal against Udinese before missing the final part of the season due to new injuries. 

At least Maldini and the club were finally able to extend the contracts of Giroud and most importantly the one of Portuguese star Rafael Leao. The announcement is expected to take place in the upcoming days, but keeping him at the club is definitely what the fans needed especially after the European disappointment. 

There are no doubts that the club's directors, and Pioli himself, made some mistakes during the season, but the remaining three Serie A games will be crucial to understand what's next at the Italian club. Ending up in the top four and playing Champions League soccer next season is fundamental for the owners and the whole project. If they fail, it's not difficult to imagine that something will change. Maldini's future, and especially Pioli's, are not secured yet.