Despite a summer of serious spending in an attempt to build a team capable of qualifying for the Champions League next season, Milan's stuttering performances over the past few months have highlighted a number of glaring weaknesses in the team that weren't addressed over the summer.
Buoyed by the possibility of foreign investment and a feeling of renewed purpose, Silvio Berlusconi finally saw fit to invest some money into a team badly in need of quality players to challenge at the highest level once again. The club acquired three high quality strikers: Carlos Bacca and Luiz Adriano for a combined fee of 38 million euros, as well as Mario Balotelli on loan from Liverpool.
Despite procuring a formidable strike force, in a show of typically poor planning, Milan invested comparatively little in improving the rest of the squad. Milan spent 50 million euros on Roma duo Andrea Bertolacci and Alessio Romagnoli, but otherwise failed to make any notable additions to the team. The assumption that the addition of these two players alone would be enough to address the team's weakness in the midfield and the defence was either reckless or naive. Despite their obvious quality, they are clearly not enough to raise the level of the squad on their own.
The January transfer window rarely sees the undertaking of any major transfers, but Milan must do what they can to fill in the gaps in its squad in order to have any hope of a respectable finish in Serie A. Youngsters such as Suso, Jose Mauri and Rodrigo Ely all show a good deal of promise, yet have found game time hard to come by so far this season. When they have been handed opportunities they have understandably looked out of sorts and struggled to keep pace with the rest of the side. All three would benefit from loan moves in January, ideally to other Serie A sides in order to gain valuable playing time in a less demanding environment. Should these prove successful, these players can absolutely vie for a regular spot in the team upon their return.
Milan moved a lot of dead weight in the summer, but there are still several players on the books who are not good enough to be there, even as squad players. Keisuke Honda's time at Milan would appear finally to be up. The Japanese international was given an opportunity to prove himself early in the season and failed emphatically. His lack of action since has made it almost impossible to see him having a future with the club. A January exit would be in the best interest of both Honda and Milan.
Nigel De Jong has also been linked with an exit lately. The Dutch destroyer was fantastic for Milan last season and signed an extension over the summer, but with Riccardo Montolivo asserting himself as the side's midfield focal point this year, he has fallen down the pecking order. His woeful performance against Verona Sunday will have done little to convince the powers that be they should not consider moving on the powerful Dutchman should Milan receive an attractive offer.
As for who Milan needs to buy, the key areas are central midfield and central defense. Milan's inability to dominate games and control the midfield has been a cause for the Rossoneri's struggles against the league's stronger sides and why they have failed to impose themselves over weaker opposition.
Zenit St. Petersburg's Axel Witsel would be the ideal candidate and quite possibly available in January, although not cheaply. Witsel's strength, athleticism and technical ability would be a major asset to a Milan midfield thats biggest weakness is ball retention and solidity. Whether utilised in front of the defense or in a more advanced position, the Belgian could form a major piece of the Milan midfield puzzle, and his reliability defensively would allow Bertolacci and Giacomo Bonaventura to roam forward with greater freedom.
Milan came close to signing Witsel at the end of the summer transfer window, but failed to agree a fee with Zenit. Hopefully a January transfer will be on the cards, although Milan will face stiff competition.
As for the defense, the lack of an appropriate partner for Romagnoli in the middle has been a problem on several occasions this season. Cristian Zapata, Rodrigo Ely and, most recently, Alex have all had a run in the side this season alongside the Italian Alex has done a reasonable job holding down the spot as of late, but none of the three have proven fit to hold down the spot in the long run.
Options are thin, especially in January and defensive reinforcements might have to wait until the summer. Even if Milan was to reprise its summer interest in Athletic Bilbao's Aymeric Laporte and Torino's Nikola Maksimovic (who is currently injured), the likelihood of reaching a deal in January is low. Either way, the club must look to do what they can in this area as coaching and organisation can only go so far in building a stable defence with players such as Zapata at the heart of the back line.
Being January, it's unlikely that anything too major will happen, but Milan must be prepared to make the necessary financial sacrifices in order to save what has been a poor season thus far.
Of course, had the club approached the summer transfer window properly however, there'd be no mess to clean up in the first place.