Amidst a summer spending spree on a brand-new defence, midfield and strike-force, the assumption was former Coach Vincenzo Montella would administer a three at the back formation for this season, utilizing wing-backs instead of wingers.
The arrivals of Ricardo Rodriguez and Andrea Conti had main men Giacomo Bonaventura and Spanish international Suso booted from the starting XI, unless they were able to adapt into more accommodating roles.
Further up front, north of €65m was shelled out for Andre Silva and Nikola Kalinic, with 20-year old Patrick Cutrone also becoming part of Montella’s plans after the plug was pulled on his loan move to Crotone.
Once Fabio Borini became the lone wide attacker to enter the fray from Sunderland, it became clear the Rossoneri saw little value in having multiple true wingers.
Now, ever since Gattuso replaced Montella and pledged his allegiance to the current 4-3-3, their mindset has changed to one desperate for aid out wide.
If Milan are serious about committing to this shape for the remainder of the season, their activity in the January transfer window is where we will see it.
The Lombardy giants have a month to add a difference-maker on the left flank who could break down opposing sides and provide an attacking threat capable of unlocking the game at any point – and there are plenty of options for Milan to explore for the left-wing, some more realistic than others.
Paris Saint-Germain’s Julian Draxler and RB Leipzig’s Emil Forsberg tick all the boxes supporters would love in this area; silky smooth on the ball, and with both the creative and attacking verve required to ignite a side.
Yet, after spending upward of €250m last summer, it’s highly unlikely Massimiliano Mirabelli and company will court expensive targets with price-tags above €30m. But, based on the fact the club invested heavily by banking on a Champions League berth, perhaps one last high-profile name is in the budget.
Then, there are second tier options that are not only young in age, but also more cost-efficient and can easily provide what Milan are looking for.
Udinese’s emerging Czech star Jakub Jankto is widely recognised as a box-to-box midfielder, but certainly boasts the means to be an effective wide player capable of floating around the final third, as he currently does under Massimo Oddo. He can also serve as a deputy to Franck Kessie, which is another area Milan could look to strengthen.
Certainly, bringing in a 21-year-old like Jankto wouldn’t disappoint, as he is highly coveted all over Europe, but prying him away from the Friuli before the summer when the Zebrette can open a serious bidding war for his signature is no easy feat.
It goes without saying, the logical choice for Milan to satisfy their winter shopping list would be Barcelona’s Gerard Deulofeu.
The 23-year-old spent six months at San Siro during the 2016-17 season, scoring four goals and adding three assists in 17 Serie A appearances to aid the Rossoneri’s run to a Europa League berth. Deulofeu’s blistering pace and dribbling ability would be the missing ingredient for Gattuso’s side, as his speed gives him the licence to take on defenders, and allow for a more direct, counter-attacking brand of football.
Currently, Deulofeu seems like the ideal fit for Milan, but because he kicked on in short time last season, several other Italian clubs appear to have thrown their name in to the hat for his signature – including Inter, Roma and Napoli.
Should the Catalan club seal the deal for Liverpool’s Philippe Coutinho, the Spanish side would be much more willing to sell Deulofeu, for the simple fact they would have no use for him with Ousmane Dembele returning from injury and reclaiming his rightful starting role. The question is will the player be open to yet another loan move? That remains to be seen.
Milan must make adding a left-winger their number one priority this month, even above adding a back-up for Kessie. If the Rossoneri are to make a second half surge and compete on all three fronts, finding a viable upgrade on the left flank cannot fall by the wayside this month.