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AC Milan 2018-19 Season Preview: Can the Rossoneri secure a top 4 finish?

After a summer full of ups and downs, Milan’s season is finally about to start. Will they win in their battle for top 4?

AC Milan v Manchester United - International Champions Cup 2018 Photo by John McCoy/International Champions Cup/Getty Images

AC Milan, the sleeping giants of Italian football, came into this summer with little to no expectations. Financial Fair Play violations were looming over the head of the club, as UEFA had broke with precedent by dropping the hammer of a European competition bad, something that had never been levied against a club that had failed to meet the “break even” FFP requirements.

Meanwhile, the Chinese ownership group led by Yonghong Li was in the process of attempting to delay the defaulting on a large loan from Elliott Management. The hedge fund’s anticipated repossession of the club also loomed large of the future of Milan, as no one knew exactly what the so-called “vulture fund” had in mind. There was no anticipation of an active transfer market, and little expectation of a meaningful season with a European ban in place, not to mention a potential financial crisis as the club struggled to meet its obligations.

That all changed when Elliott took control of the club. To the pleasant surprise of many, Elliott Management invested capital into the club to clear Milan’s debt and committed, at least in the short term, to the financial and on-field success of the club. That included clearing out the board that the previous owners had installed. Out went Marco Fassone and Massimiliano Mirabelli. In came club legends Leonardo and Paolo Maldini.

And so begins yet another “new era” for Milan. The new management sent Leonardo Bonucci back to Juventus in exchange, essentially, for defender Mattia Caldara and striker Gonzalo Higuain plus cash. They then brought in Tiémoué Bakayoko to add to the midfield, and are linked to both Diego Laxalt of Genoa and Samu Castillejo of Villarreal, both of which are likely to join in the next few days.



Mattia Caldara (CB) for Leonardo Bonucci

Gonzalo Higuain (ST) for €18 million on loan, with €36 million option to buy

Tiemoue Bakayoko (CM) for €5 million on loan, with €35 million option to buy

Pepe Reina (GK) on a free transfer

Ivan Strinic (LB) on a free transfer

Alen Halilovic (Winger) on a free transfer

(potentially) Samu Castillejo (RW/LW) for €3 million on loan, with €15 million obligation to buy and Carlos Bacca

(potentially) Diego Laxalt (LB) for €18 million, minus €11 million as part of Gianluca Lapadula’s move to Genoa


Manuel Locatelli (CDM) on loan to Sassuolo for €2 million with obligation to buy for €10 million

Nikola Kalinic (ST) to Atlético Madrid for €15 million

André Silva (ST) to Sevilla for €5 million on loan, with €30 million option to buy

Leonardo Bonucci (CB) to Juventus for Mattia Caldara

Carlos Bacca (ST) to Villarreal as part of the deal for Samu Castillejo

Gustavo Gomez (CB) to Palmeiras for €1.5 million on loan

With Caldara and Higuain, Milan added two valuable pieces to their starting lineup. Caldara can form a partnership with Alessio Romagnoli that can last for years in Serie A, while Higuain presents a solution to Milan’s striker problem from last year. Castillejo and Laxalt would be valuable in terms of depth and rotation as possible starters, and Bakayoko is a low-risk, high-reward addition in the midfield.

The hole in Milan’s lineup is, as it has been for years, in the midfield. Giacomo Bonaventura is a lock for the left side, and Franck Kessie has the right side, but the center of the midfield has a question mark. With the departure of Locatelli, Milan has Bakayoko, Lucas Biglia, and (somehow, still) Riccardo Montolivo for the center of the pitch. Although Milan has depth now at left-back (Rodriguez, Laxalt, Strinic) and right-back (Davide Calabria, Andrea Conti), where they did not before, there is still a problem in the midfield, which could still use an addition.


Milan, barring a change from manager Gennaro Gattuso, looks set to play a 4-3-3 consistently.

GK: Gigio Donnarumma (Pepe Reina)

RB: Davide Calabria (Andrea Conti, Ignazio Abate)

CB: Alessio Romagnoli, Mattia Caldara (Mateo Musacchio, Cristian Zapata)

LB: Ricardo Rodriguez (Diego Laxalt, Ivan Strinic)

LM: Giacomo Bonaventura (Andrea Bertolacci, Jose Mauri)

C(D)M: Tiemoue Bakayoko (Lucas Biglia, Riccardo Montolivo)

RM: Franck Kessie (Alen Halilovic, Bakayoko)

RW: Suso (Samu Castillejo, Halilovic)

ST: Gonzalo Higuain (Patrick Cutrone)

LW: Hakan Calhanoglu (Castillejo, Fabio Borini)

Gattuso also may explore having a 4-2-3-1 at times, keeping the back four as-is with Kessie and Bakayoko sharing the defensive midfield responsibilities, and moving Calhanoglu to the number 10 role. That would move Bonaventura into the attacking left spot, or would let Castillejo slide in.

Under the new management of Elliott, Gattuso’s position as manager of the club appears to be secure. Gattuso will lead the team through Serie A, where they finished sixth last season, and Coppa Italia, which they made it to the final of last season. Milan will also compete in the Europa League after having the FFP ban overturned by the Court of Arbitration for Sport.

In Serie A, Milan has an uphill road to climb. Juventus may be stronger than ever with the addition of Cristiano Ronaldo, and are in the best position they have ever been in to win the Champions League. Inter Milan, who finally returned to the Champions League, have had one of the best transfer windows in Europe, adding several pieces that have solidified the blue side of Milan as one of the best teams in Italy. AS Roma have also improved their squad after finishing third last season, and Napoli hired Carlo Ancelotti after finishing second. Then, there are Milan and Lazio, battling for fourth place with a best-case scenario of third, and a worst-case scenario of seventh, with Atalanta also battling.

An optimist would say Milan, after having a surprisingly good transfer window, are in a spot to compete for fourth and get back to the Champions League for the first time since 2013-14. One who is not so confident would say that Milan had to deal with a summer that was shortened by not only the World Cup, but also the saga of the ownership and Financial Fair Play. That has led to Milan being not optimally prepared, with a couple new players coming in just days before the start of the season. One who is doubtful of Milan may say they are, at best, the fifth best team in Italy, and that is just slightly over Lazio. Another may say that Milan is a lock for sixth.

Milan have improved from last season. While the center of the midfield led by Bakayoko, who Milan fans are hoping to turn his form around, is a concern, the rest of the team took a step up. Higuain solves the striker position. Suso is who he was last season. Calhanoglu stepped into his role and excelled, particularly at the end of last season. Bonaventura should be able to rebound from his poor season. Kessie has only gotten better. Caldara and Romagnoli will be there for years to come. Gigio has another year of experience. And the defensive backs finally have competition behind them and the ability to rotate, as do the wings. This team will thrive under another year of Gattuso’s leadership and the consistency provided not only by him, but the security of the management in charge of the club.

Milan, this summer, were able to step out of the shadows of doubt, whether in their ownership situation or in terms of European competition. Milan may not be competing for the Serie A title, but will be in a battle for the two spots in the top four that are up for grabs with Napoli, Roma, and Lazio. Anything less than Europa League would be a shock, and anything more than a fourth place finish would be impressive and more than encouraging. Milan will look to go as far as possible in the Coppa Italia and improve on the demolition that occurred in last year’s final, and will also hope to make a run and get a more fortunate draw in the Europa League. This is Milan’s chance to truly start their new era off on the right foot.