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Rating AC Milan’s Summer Transfer Window

Grading How Well Milan did During the Summer Transfer Window

Paolo Maldini, technical director of AC Milan, looks on... Photo by Nicolò Campo/LightRocket via Getty Images

In May 2019, former Arsenal and current AC Milan CEO, Ivan Gazidis gave an extensive, eye opening interview with Italian media house La Gazzetta Dello Sport, detailing the current financial handcuffs of the club while offering the keys with which the club could get out of them. In the interview, Gazidis also laid out the blueprint by which the Rossoneri’s transfer plan would be governed stating “our strategy is not to invest in Top players or those who have already been, but in those who can become top players with our jersey”.

With Italy’s summer transfer market for incoming purchases closed (players could still be sold and free agents signed), factoring in Gazidis’ statements is of paramount importance if a fair grade is to be attributed to the team. Below I take a look at all the new players that AC Milan have acquired over course of the transfer window and attach grades for each player ranging from F to A. A final grade for Milan’s overall market will be given at the end. We’ll go in chronological order starting with the first move made official by the club; coach Marco Giampaolo.


Arrived from - Sampdoria

Much has been made about the appointment of the Swiss born tactician. Considering the lack of attractive play by Milan last season and lack of goal scoring opportunities, one could understand management’s mindset with the hire. Under Giampaolo last season, Sampdoria boasted one of the league’s most attractive styles, capable of creating numerous chances through their possession based and high pressing system, as evidenced by the capocannoniere, coming from the Genoa based club, in Fabio Quagliarella.

AC Milan v Brescia Calcio - Serie A
Milan New Manager, Marco Giampaolo
Photo by Giuseppe Cottini/NurPhoto via Getty Images

Questions did arise however, as to whether or not coach Giampaolo was actually ready to make the jump to a top 4 contending club or if he merely a great mid-table club manager as his teams finished 10th, 10th, 10th and 9th in the last 4 Serie A seasons. In order to accurately rate Milan’s coaching hire however, you must consider Milan’s financial constraints and ask yourself the question: what other available coaches could Milan have obtained without granting them the proverbial war chest to build their squad?’ The list of possible candidates dwindles considerably, with the likes of Sarri, Allegri and Conte immediately off the board, while Gasperini was never going to leave Atalanta after securing Champions League.

Given Milan’s ambitions to return to the coveted Champions League places, their limited available resources to reinvest into the club and the limited list of available alternatives, Giampaolo’s hire proves a risk worth taking.



Positions: LB

Arrived from: Real Madrid, 20,00 Mill. €

Why purchase a left back when we’re perfectly covered in that position? Isn’t Hernandez is a Real Madrid flop? Does he even know how to defend well? All questions asked by Milan fans following the acquisition of Theo Hernandez. All legitimate concerns. All devoid of full context.

Hernandez provides physical and technical tools that Ricardo Rodriguez simply does not. His blistering pace, combined with the ability to take on his man is something that Milan has lacked from the LB position in over a decade. While Rodriguez may be more disciplined defensively, imbalance going forward has plagued Milan for the past 3 seasons. Not only do Milan have an attacking spark plug in Suso on the right, but they’ve also had the likes of Davide Calabria and Andrea Conti to provide support, while the left has been neglected, making the team that much more predictable. With the arrival of Hernandez, Milan finally have their dynamic left back who is able to provide an outlet on the left and provide width for a Giampaolo system that is notoriously narrow. Given the exponential rise in transfer cost this past decade, 20 million for a 21yr old also doesn’t seem expensive.

It remains to be seen whether or not Hernandez’ propensity to attack will leave the defense exposed, which could seriously determine how this transfer is looked in a few years, but there’s no doubt his pace and skill is something we need at the position.



Position: CM

Arrived from: Empoli, 8,00 Mill. €

Milan had an grandiose exodus from the midfield department at the beginning of the transfer window. The departures naturally left the club thin in the middle of the park, prompting the club to address this area of need.

Krunic provides valuable depth to the club after having his best season statistically for Empoli, scoring 5 times and providing 7 more assists for teammates. To expect similar returns for the 25 year old Bosnian however, might be expecting too much as Krunic most likely will see nowhere close to the number of minutes he saw last year for the relegated Empoli. A player with a powerful shot and knack to score beautiful long range goals, Krunic offers little else in the middle of the park and at 25 years old does not project to get significantly better.

It’s always difficult to argue against a price tag of 8 million € however, but its difficult to envision how Krunic fits into the blueprint of Milan’s transfer strategy.



Position: CF,SS

Arrived from: Lille, 25,00 Mill. €

Leao’s signing was not one to necessarily, fill a position of absolute need as at the time the team was flush with forwards, in Cutrone, Andre Silva and Piatek, while actively pursuing a deal for Angel Correa. Leao was purchased, partly due to what he could contribute this season, but ultimately because he has been identified as one of the most exciting young players in world football. In fact, rated Leao’s potential as 10/10. To provide context the same potential rating was attributed to Joao Felix and more than Brescia’s Sandro Tonali (9.5/10).

Leao’s purchase, in keeping with Gazidis’ comments, was one for the future. A player with loads of potential, who has the ability to contribute right away given his goal scoring return for Lille last year (8 goals in 16 starts). With the sale of Cutrone and Silva, Leao remains the only like for like replacement for Piatek up top, so he should receive his fair share of minutes, leading the line for Milan.

Considering Leao came in for one fifth the cost of Joao Felix, the purchase doesn’t seem to be that much of a risk, taking into account his extremely high ceiling.



Position: CDM,CM


Milan’s regista position has arguably been the most in-need position at the club the past 5 years. Multiple players have tried their feet at the position, to very little success. That’s why the acquisition of Bennacer has the potential to be the signing of the summer, not only for Milan, or Serie A but for all across Europe. After the divorce between Milan and Bakayoko at the end of last season, Milan was hard pressed to find a suitable replacement for the Frenchman. Not only does Bennacer approximate what Bakayoko does defensively, he’s contributes much more in the attack that the Chelsea player did. In fact, Bennacer was among the top players last season in interceptions and was atop all midfielders in that stat, while Bakayoko was 5th among midfielders in registering interceptions. Bennacer also topped Bakayoko in dribbles last season, earning top spot again among all central midfielders.

The Algerian’s acquisition checks all the boxes for Milan. Young, extremely cheap, prodigiously talented and fills a position of need. Bennacer followed up his impressive campaign for Empoli, with a championship win at the African Cup of Nations, while also taking home player of the tournament honors, in a tournament that included the likes of Sadio Mane, Riyah Mahrez and Mo Salah. To secure a signing of this magnitude for the price that Milan did, represents extremely shrewd business and low risk to the club.



Position: CB

Arrived from: Flamengo, 11,00 Mill. €

Its difficult to determine Milan’s mindset with the Leo Duarte acquisition. After being heavily linked with and eventually priced out of many central defenders this summer, the Rossoneri settled on another Flamengo product in Leo Duarte.

The signing evoked emotions from a similar acquisition Milan made a number of years ago in Gustavo Gomez, who ironically left the club for Brazil this year. Gomez failed to leave his mark and one could only hope that Duarte doesn’t succumb to a similar fate. How this transfer would be remember, would be heavily based on how Duarte adapts to a more tactically disciplined league in Serie A. At 23, Duarte isn’t the youngest of prospects, but there’s still room to grow, even if playing time initially could be hard to come by, especially with the expected return of Caldara in the not too distant future.

Duarte may still be young, but questions remain as to whether or not Milan sufficiently secured a position they clearly wanted to reinforce this summer. The fact that Milan was pushing for Demiral once again at the end of the window, suggests maybe they themselves aren’t sold on the Brazilian.



Position: CF,SS,LW

Arrived from: Eintracht Frankfurt, Loan

Another name that seemingly was not atop the Rossoneri’s wish-list, but became an eventuality is that of Ante Rebic. Although Milan was linked with Rebic earlier in the summer, he was not the first choice of the Rossoneri for the attack.

Rebic was an integral part of a prolific front three for Eintracht Frankfurt last season. A player with immense pace, good dribbling and vision and an ability for spectacular goals, the Croat provides Milan with something they’ve been lacking for years, a pacey, direct, powerful runner. A player who’s had experience in Serie A previously with Fiorentina and Hellas Verona, Rebic managed a respectable 10 goals and 6 assists in 38 appearances last season for Frankfurt.

Rebic’s move however, cannot be looked at in a vaccuum. His 2 year loan swap with Andre Silva, means the two will be inextricably linked for at least the next 2 years. Given the fact that Milan seemed desperate to move on from Andre Silva, his involvement in the deal for Rebic could be considered a win-win for the Rossoneri. It would be difficult to try to predict how Rebic would do at Milan, but given that his strengths have been something the club has been missing for a number of years, one could surmise his addition should assist the club in its quest for Champions League.


It’s important to judge Milan’s mercato, by taking into account all variables, including financial fair play, limited financial resources, player sales, player acquisitions andaddressing areas of need among others. AC Milan were able to build upon a young core with extremely talented youngsters in Hernandez, Leao and Bennacer. They astutely followed the transfer policy as set out by Ivan Gazidis and brought one of the brightest coaching minds on the Italian peninsula. They did make some questionable signings in Duarte and Krunic, but for 20 million in total between the two players one could hardly complain that they over spent.