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AC Milan Season 2019/20 Review: The Summer Transfer Window

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This series will look back at the thrills and spills of the AC Milan season. Some pieces will look at individual season-changing moments, and others will look at long stretches of upheaval. Hopefully, they will all provide clarity to the season.

Hellas Verona v AC Milan - Serie A Photo by Alessandro Sabattini/Getty Images

AC Milan started the summer of 2019 without a coach and without European competition (which they had been removed from because of Financial Fair Play). The summer transfer window has a reputation as the roster-changing and season-defining point in the calendar. Milan made their purchases and sales during the window and overhauled the team, again. Some of these purchases were successful, some of them were not. I will rate these transfers on their initial price, who else was available in that position in that price range, and then how they have panned out. Some may surprise, some may not.

All transfer fees are from Transfermarkt.

The Best of the Best

I am going to start with the homerun transfer, Ante Rebić. This was a loan swap deal that involved André Silva. While this move was fairly lateral in terms of output and talent exchanged, both players desperately needed to change clubs. Silva and Rebić had eerily similar statistics throughout the 2018/19 season. The Croatian man was more prolific and had higher expected goals and assists numbers. Both finished their domestic seasons with nine goals, Rebić had four assists to Silva’s none, and both players needed to find greener pastures. Silva had found some success in Spain but was desperately looking for consistency, and Rebić had made his wish to leave Eintracht Frankfurt public (they had just lost Sébastien Haller and Luka Jović). At first glance, this loan deal was a win for the players and the teams. This is low risk, high reward to its maximum extent.

Then the season started. Marco Giampaolo decided that he had no space in his lineup for Milan’s new Croatian forward and Rebić spent much of the first half of the season stapled to the bench. Silva began the season with three goals and an assist in his first five Bundesliga starts. Then the Portuguese man went ice cold until February. In this time, Rebić took off at Milan and started scoring at will. His revitalization after January showed the Rossoneri the potential of his play. They both ended the season on an absolute tear and showed their respective clubs how important they are. Silva had higher expected goals, assists, and per shot rates than Rebić over the course of the season, but the Croatian forward finished better than the Portuguese man. Overall, this was an undeniable win for both teams, and it would be a shame for either side to lose their loanee. I rate both players well and hopefully, permanent transfers are found for the two.

Ismaël Bennacer was one of Milan’s top and key performers throughout the 2019/20 season. He started his Serie A career with Empoli FC. Immediately, his potential was evident to all who watched the young Algerian midfielder. His knack for making destructive tackles and then immediately progressing play forward was awe-inspiring. He was an absolute must-sign player for Milan, and the team did just that. Now, he has turned into the core player in Milan’s midfield for what seems to be years to come. Imagining a future Milan without Bennacer in the midfield is almost heresy. Milan spent $17,600,000 to purchase the player and that was money incredibly well spent. Other more defensive midfielders purchased near this price tag were Philip Billing, Stefano Sturaro, Douglas Luiz, Nahitan Nández, and Joan Jordán. None of these players are even in the same stratosphere of talent as Bennacer. This transfer was an absolute home run.

Frustrated at The Time but Turned Out to Be Smart

Theo Hernández was a $22,000,000 left-back signing from Real Madrid CF in the summer. The Frenchman played sixty-nine matches in Spain before moving to Italy. In these matches, he scored two goals and had five assists. His defensive play was concerning because of his defensive positioning, but he had shown promise with his tackling. The makings of a strong left-back were evident, however, there was still some concern whether he could take a step forward in his development.

What happened in Milan was unpredictable. He started the season as Milan’s most dangerous attacker. A strange sentence to describe a fullback. By the end of the season, he scored six goals and contributed three assists. That more than doubled his goal contributions in one season. However, he still had to prove that he could handle his defensive responsibilities. While still chaotic defensively for most of the season, Theo showed that he was growing as a player and as a defender. There is still room to grow but he showed his talent all season. This transfer, while still pricey, has ended up being more than worth it so far.

Patrick Cutrone seemed like a lifelong Milan player. He signified everything that a team would love, youth academy product who plays for the badge, and reminds everyone of a club legend. However, Milan had three other players in his position, one of which was a more finished version of the type of player Cutrone seemed destined to become, Krzysztof Piątek. While I have my qualms with the signing of the Polish striker for $38,500,000, Milan needed to give him more time to integrate into the squad. Having two players in this role made no sense, so Cutrone had to leave. Wolverhampton Wanderers would come to sign the player for $24,200,000 in the summer.

The young Italian man never broke into the English side consistently and only scored two goals. He would leave later in the year and travel to ACF Fiorentina where he still has mainly been used as a super-sub. He has not noticeably developed as a player since the 2017/18 season. He is still only twenty-one, but Milan receiving a sizable fee for the player has been positive. This transfer hurt the heart but was the sensible action to take.

Initially Optimistic but there are Concerns

I love Rafael Leão, I want that to be clear, however, I am concerned about his role and utilization. He is much more versatile than Cutrone, even if both had eerily similar traditional statistics this season, but he and Cutrone have faced similar issues breaking into their respective new squads. When Leão was signed for $25,300,000, I jumped for joy. He had been turning heads at Lille OSC and showed his potential throughout the 2018/19 season. Initially, the fee was acceptable. Now, Leão seems like he has flummoxed Stefano Pioli about how to deploy him. While I agree that Leão could easily become a support striker, I am concerned that he will be turned into a winger, which he is not. He has incredibly high potential, but Milan’s staff needs to facilitate his growth. He should see more minutes at striker next season. Hopefully, he will deliver when he receives more opportunities.

The Forgettable Transfers

Léo Duarte was purchased from Clube de Regatas do Flamengo for $11,000,000 and Rade Krunić from FC Empoli for $8,800,000. Neither purchase changed much during the season and both were intended to build depth. However, neither player was of the appropriate quality to play in Milan. Almost twenty million spent on two depth players was never advisable. Milan may get their money back on both purchases, but the decision from the beginning was ill-advised. Depth players are difficult to acquire, and neither of these players was able to maintain their place with the Rossoneri.

Rating the Window

You may have noticed that I did not talk about the Franck Kessié or the Manuel Locatelli transfers. These two were future fees that were triggered during the last summer. Milan signing Kessié was smart, Milan selling Locatelli was incredibly foolish. However, I do not consider these deals as part of the window because they were already agreed upon.

Overall, the 2019 summer window greatly changed the trajectory of Milan by filling major holes within the Milan side. Three of the additions have turned into core building blocks of the future and the third, Leão, has elite-level potential. While Milan brought in six players during the window, they also jettisoned ten players who no longer provided value to the team. Cutrone may have been a tough pill to swallow, but the other players saved millions in wages for Milan. There was a noticeable statement of intent from Milan during the summer transfer window. The average age of the arrivals was twenty-one and a half and the average age of the departures was twenty-four and a half. Both are young, but Milan got three years younger.

The next thing to get right was the managerial appointment, which I will talk about next.