The Three Positions That Milan Should Address This Summer

After the disappointing start to the 2019-2020 season, newly-appointed Milan manager Marco Giampaolo was sacked by the club as early as October. His replacement Stefano Pioli was only able to bag a series of mixed results throughout the “normal” part of the season.

But just when everyone was awaiting another summer of turmoil in the red part of Milano, with yet another “new project” being drawn – this time spearheaded by Red Bull’s Ralf Rangnick who would become both coach and director of sport at Milanello, something changed after the restart of the season in June, and for once, it was a change for the better.

While several clubs lost their ways after the restart, suffering both physical and mental fatigue, a young Milan side led by the legendary Zlatan Ibrahimovic was delivering some of the best football the team has played in years, with the main highlight being the historical 4-2 comeback against Juventus.

Milan scored four goals against Juventus for their first time since March 1989 (4-0)

Luckily for Pioli, his team’s late charge was enough to save his job and that of the club’s technical director Paolo Maldini, as Rangnick’s name suddenly became a distant memory with former CFO Zvonimir Boban being the only main casualty for the German’s ghost at Milanello.

Although that excellent late run could prove to be a focal point for the team in the buildup for the future, the club’s directors would be foolish if they try to use it as a mask to hide the squad’s weak points.

So how should the Rossoneri proceed in this transfer market knowing that they are running on a budget that could be as low as 30M euro?

The reported signing of Real Madrid’s Brahim Diaz can be considered a decent start in this tough economic situation. The former Manchester City prospect can help in solving Milan’s problems on the right-wing.

But three other main departments must be upgraded as well during the summer. And those positions are the following:


  • Status Quo:

While the real quality of club captain Alessio Romagnoli is still a topic of debate among some Rossoneri fans, there’s no denying that the 25-year old Italian international has earned his starting spot and captaincy with solid performances throughout the years.

Unfortunately for Milan, the rest of the department isn’t as assuring. Mateo Musacchio and Simon Kjaer might be decent defenders, but surely Milan deserves a little better quality than the two veterans can offer.

Milan recorded a total of 46 goals conceded in the Serie A season 2019-2020

Leo Duarte suffered two major injuries which kept him out for almost the entirety of his debut season in Milan, so the Brazilian remains a hidden package. Meanwhile, Paolo Maldini would do well to send Matteo Gabbia on loan to earn some vital experience.

On the other hand, Mattia Caldara looks reignited since his return to Atalanta on loan. Although The young Italian would be a good addition to the Milan backline, he seems to adapt better in the heart of Gasperini’s three-man defense.

  • Our Suggestions:

Milan’s former defender Thiago Silva has been linked with a return to the club after confirming his departure from PSG, but the Brazilian veteran is reportedly very close to signing for Chelsea. And Although Silva’s departure in 2012 left a huge hole that perhaps hasn’t been properly filled until this day, another nostalgic signing is not exactly what the club needs at the moment as the aging Selecao defender is not the same player he was 8 years ago.

On the other hand, Fiorentina captain German Pezzella (reportedly another Milan transfer target) could be the perfect playing partner that Romagnoli needs. A natural commander in the air blessed with a smart sense of positioning, at 29 years of age the Argentine international is at the peak of his power and should be thrilled to make a big career step-up.

After a loan spell with Fiorentina during the 2017–18 season, Pezzella signed a five-year contract.


  • Status Quo:

Most Milan fans would agree that their club urgently needs a new right-back this summer. Rotating between Andrea Conti and Davide Calabria has been a “pick your poison” task for Stefano Pioli with neither player managing to inspire. The brilliance of Theo Hernandez on the Left side further highlighted his two teammates’ shortcomings on the other flank.

Last Tuesday, Director Paolo Maldini assured that the club won’t sell Calabria this summer. On the other hand, Conti’s future wasn’t mentioned at the press conference. So is the club going to sacrifice the former Atalanta player in favor of a better option in this department?

  • Our Suggestions:

Tottenham Hotspurs’ Serge Aurier has been the most strongly linked player for this position. And despite the directors denying the reports of his arrival, things could still change during the market period, especially if the Spurs complete the signing of Wolves’ Matt Doherty which would push the Ivorian bad boy even further away from the North Londoners.

Although Aurier could be considered the best right-back option on the market, our suggestions for alternatives include Chelsea castaway Davide Zappacosta who should be healthy again by the start of next season, Lazio’s Adam Marusic who lost his starting spot for Manuel Lazzari, and also versatile Torino veteran Christian Ansaldi.

Zappacosta joined Roma on loan from Chelsea


  • Status Quo:

By the end of last season, Franck Kessié and Ismael Benaccer had cemented themselves as one of the best partnerships in Italy at the double-pivot role.

But the two young Africans won’t be enough to hold the midfield for the entire season, especially in light of Milan’s possible return to European competitions.

Coach Pioli possesses a host of attacking midfielders at his disposal, but few are the ones capable of covering the deeper part of the midfield. Meanwhile, Lucas Biglia should be allowed to leave sooner rather than later as the tired Argentine is no longer capable of holding the middle of the pitch, and Rade Krunic has been scarcely used last season which isn’t a good sign for the Bosnian’s future at Milan.

Promising youngster Tommaso Pobega will add some depth to the midfield and perhaps a little more, but the squad still needs one or two additional central-midfielders.

  • Our Suggestions:

Despite some reports claiming that Milan could snatch Brescia’s wonder-boy Sandro Tonali from under their neighbors’ noses, the majority of sources agree that the youngster will eventually sign for Antonio Conte’s Inter.

Liverpool’s Marko Grujic has also been mentioned as a potential signing, but all roads lead to Chelsea’s wantaway Frenchman Tiemoué Bakayoko who had previously impressed while on loan at Milan during the 2018-2019 season, and he’ll reportedly agree to halve his wages in order to rejoin the Lombardy club in a deal that would definitely benefit all parties involved.

On 31 August 2019, Bakayoko agreed to rejoin Ligue 1 club Monaco on loan.