Why Montella Is Facing His Toughest Test Yet

​AC Milan are currently in the midst of a historical and stunning transfer campaign that will go down as the most expensive transfer window conducted by an Italian club, and with 10 new faces set to don the famous red and black strip, Vincenzo Montella must surely feel that Christmas has arrived early at Milanello this year. However, the money spent doesn’t guarantee success, Rossella Marrai-Ricco takes a look at why Montella is currently facing the toughest test of his career.

Things are happening at Milan. It seems an odd thing to say, but for several years the Rossoneri have passed through transfer markets signing free agents, taking weeks to secure a deal, and then signing up players largely considered “not Milan quality”.

Times have changed. Silvio Berlusconi’s 31-year spell as owner of the sleeping giants was brought to an end in April, and new owner Yonghong Li has taken over. His takeover has seen him welcome the arrival of Marco Fassone and Massimiliano Mirabelli, and with them, a blank check. Or so it seems.

No longer shackled by the financial constraints of Berlusconi’s inability to invest fresh money into the club he turned into greatness in the late 80s and 90s, the management duo have started to rebuild a competitive squad from scratch.

Well aware that the Rossoneri’s season would commence a month earlier than normal, due to Europa League commitments, Fassone and Mirabelli got to work fast…

Mateo Musacchio was the first to arrive before the Serie A season had even ended, Franck Kessie soon followed, along with Ricardo Rodriguez. Then a scoop out of nowhere for Portugal’s most promising talent, Andre Silva, was secured for a bargain fee of €35 million.

It didn’t end there though... Fabio Borini was snapped up on loan from Sunderland, and while he isn’t considered as glamorous a signing as the other new arrivals, he has a relationship with Montella and will provide necessary depth and versatility to the squad.

Every European club was then left in envy when the continent’s most lethal set-piece taker, Hakan Calhangolu, appeared at Malpensa airport ready to pen in a contract with the Diavoli. His arrival at Casa Milan saw him greeted by a mass group of fans, along with Andrea Conti, who missed his vacation in order to become the seventh signing of the new Milan era.

A brotherly affair soon followed, with Gianluigi Donnarumma deciding to go back on his original decision and pen in a new and improved contract with the team he grew up supporting. Upon pleading for the fans’ forgiveness, his older sibling Antonio was also re-signed to become the club’s third choice stopper. Queue quadruple handshake, and a ‘schiaffo’ from Mirabelli.

Many thought that was the end of Mirabelli’s magic, and with pre-season having officially begun, few were expecting the unthinkable to happen. Enter Leonardo Bonucci.

It took just 48 hours from when the first ‘rumour’ of him being linked to Milan turned into chaotic and joyous scenes at Casa Milan. There, he was greeted by a couple of hundred fans, was given a tour of the Milan Museum, before eventually putting pen-to-paper in a deal which cost Milan a mere €42 million in transfer fees – a steal for one of the world’s best centre-backs.

Rossoneri management hasn’t stopped there though, as Lucas Biglia is just hours away from completing his move to the red and black side of the city, and there are still reports that one of Andrea Belotti, Nikola Kalinic, Renato Sanches or Pierre-Emerick Aubameyang could join too.

On paper, the transfer window has been nothing short of impressive. Largely surreal for the loyal Milanista, but much needed for a club in desperate need of competing in Europe and for domestic glory again.

Last year, Montella managed to get his squad to punch above their weight… Securing their first piece of silverware back in December against Juventus was no pure fluke; he found a way to instil cohesion, unity, and a hunger amongst his players. Above all, was able to avoid any of the off-field problems with the takeover from filtering through into the squad.

The former Fiorentina tactician created a safe environment for his youngsters to develop and mature in, while he also liked to balance his squad out with experienced personnel across each department on the field.

What is most notable, though, is that most of his players had already worked alongside each other for at least one season, whereas, this year, he affectively has a brand new starting XI at his disposal.

This is where the tricky part comes in…

Out of the new arrivals, only Conti and Kessie have previously worked alongside each other at club level – at last season’s surprise package Atalanta. The Italian full-back did, however, spend the summer playing alongside his new teammates Donnarumma, Manuel Locatelli and Davide Calabria at the U21 Euros, and he is expected to form part of a completely new backline at Milan.

Last term, Montella stuck to his favoured 4-3-3 system, but with the arrival of Bonucci, Conti and Rodriguez, he now has the tactical flexibility to shift and change formations easily.

Conti and Rodriguez undoubtedly boast incredible skills going forward, and possess the pace to overlap and drop back when needed, making them available to play in the wing-back or full-back roles. Meanwhile, Bonucci will add some much-needed experience and know-how to the backline, and it is because of his proficiency and previous success that he is likely to compliment well alongside Alessio Romagnoli, and potentially Musacchio.

The much-improved depth and versatility to Milan’s defensive department will surely see the 43-year-old willingly alternate between a back four and a back three when needed. Montella is no stranger to adjusting his formation to a back three, having done so at Fiorentina.

The midfield dynamic will be an interesting one. Considering Milan spent over €50 million to refurbish that department, Montella will need to juggle the demands of each player carefully.

Kessie is raring to go, while Locatelli and Montolivo will want to compete for their place in the squad. Calhanoglu will feel he is deserving of a starting berth, despite spending the last four months of the 2016/7 campaign suspended. The same will apply for Lucas Biglia, as he will expect to be the conductor in the middle of the park, following another solid campaign with Lazio, while Suso was one of Milan’s best players last term. Although, that doesn’t mean he is guaranteed a starting spot either…

Gianluca Lapadula’s exit means Carlos Bacca and Patrick Cutrone will likely act as back-ups to Andre Silva up front. Some would say, all these options is a good headache to have.

The influx of players, different nationalities, personalities and languages will, however, mean that it will take some time for the squad of players to adapt to their surrounds, adjust to their new teammates and formations, and fully understand Montella’s coaching philosophy.

Last year, the Napoli-born coach led Milan to fifth place on the Serie A table and to their first trophy in six years. It was a good outcome considering the players he had at his disposal, and with latest investments having already generated massive hype, there is already talk of the Rossoneri being title contenders.

This year, the pressure to succeed almost immediately will be expected from both the media and fans – something last year’s squad didn’t have to worry about. Not to mention, the Rossoneri will also be participating in the Europa League, adding an extra competition that wasn't there before. This is what makes it Montella’s biggest test so far.

He will have to find a way to stave off the pressure, fina a way to equally utilize his squad between competitions, and man-manage his players in the same quiet and professional manner he conducted himself with last term. He, his players and club management must accept that it will take time for his squad to become a ‘well-oiled’ machine, but there is a delicate line… If it takes too much time, then he will start to feel the heat, and questions will be asked.

After 12 months of being able to go about things rather quietly, and with no severe weight of expectations on his shoulders, Montella will now be tested in a new manner. It will be interesting to see how he fares.