Scouting AC Milan Transfer Target Juan Cuadrado

For AC Milan, wingers are back on the agenda. After the tactical trials and tribulations of 2015-16, including a diamond midfield and the use of natural trequartisti in wide areas, Vincenzo Montella looks set to reintroduce true width to the team.

The head coach recently oversaw his first match in charge of the Rossoneri with a trip to France to face Bordeaux culminating in a 2-1 victory. And behind the positive result was a basic rough 4-3-3 shape which made use of two wingers in Suso and Jeremy Menez.

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With this in mind, it was perhaps inevitable that Milan would be linked to wingers as the summer transfer window rumbles on. The latest piece of speculation involves Chelsea’s Juan Cuadrado, with Il Milanista (h/t TalkSPORT) reporting that he could move to the San Siro side on a season-long loan.

The need for additions in this particular area is exacerbated not only by the new setup implemented by Montella, but because of the shortfall of options to fill in the left and right wing positions.

Giacomo Bonaventura looks set to play more of a central role under the new coach’s auspices, while Keisuke Honda is similar to the 26-year-old Italian in that he is, by trade, a trequartista who prefers to play in the hole behind the strikers. Meanwhile M’Baye Niang’s skill, movement, pace and underrated strength are likely to see him operate more often as a centre-forward, which is where he played against Bordeaux.

That leaves Suso and Menez as the only genuine wingers. However, the former made just one appearance for Milan last season before being sent on loan to Genoa for six months, and the latter spent much of the campaign out due to injury problems and is reportedly up for sale, according to La Gazzetta dello Sport (h/t Football Italia).

With the intention of solving this problem, Cuadrado appears to have become the club’s primary focus in the transfer market. But signing him would not simply be a case of adding numbers to the squad; he would significantly enhance the quality of Montella’s lineup.

The Colombian spent 2015-16 on loan with Juventus, where he made 28 appearances in Serie A, scoring four goals and setting up five. For this, he earned a commendable 7.29 average performance rating from WhoScored.com, helping the club to a fifth consecutive scudetto in the process.

He got off to a slow start with the Bianconeri, struggling to establish himself within the starting lineup. However, this was principally because of tactical uncertainty. Coach Massimiliano Allegri took time to figure out his most effective system, though when he had settled on the 3-5-2, Cuadrado often appeared in the right wing-back role.

Alternating with the more defensive Stephane Lichtsteiner, the 28-year-old offered more attacking threat down the flanks. And, in his wing-back position, he had plenty of space in which to move forward with and without the ball. He frequently acted as a wide outlet, stretching the opposition and pinning back their full-backs.

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In addition to his positioning, Cuadrado’s skillset proved effective. Excellent in one-on-one situations, only Paul Pogba and Paulo Dybala beat their opposite man more often than he did, with 2.5 successful dribbles per game, according to WhoScored. He showed his creativity in other ways too, contributing 1.6 key passes per game.

A tactically intelligent player, he was also valuable to Juventus through his understanding of how to use his body to win free-kicks. Indeed, no other player in the Italian champions’ squad was fouled on a more consistent basis.

After a successful loan spell, it was expected that the Bianconeri would sign him permanently, but Cuadrado instead made his way back to Chelsea for the beginning of pre-season. With renowned 3-5-2 advocate Antonio Conte taking the reins at Stamford Bridge it was believed the player would be given an opportunity to shine in the Premier League, something backed up by the coach’s comments last week,

Per the BBC, the 46-year-old former Italian national team boss said: “I wanted him when I was Juventus coach. He will come back very soon and train and play with us. Now, he's a Chelsea player and he'll stay with us. If something changes you'll know.”

However, since those comments speculation has grown that Cuadrado could be on his way having made just four league starts for the London club, who he joined in February 2015 for a fee of £23.3 million. And, according to Sky Sport Italia and Calciomercato (h/t Football Italia), Milan are favourites to sign him.

Purportedly, there are several reasons behind this. One is that the Rossoneri can guarantee him regular game time; another is that it would allow him to reunite with a coach who he has enjoyed playing for in the past.

Montella was appointed to the Fiorentina dugout in June 2012, and, one month later, Cuadrado signed for the Viola. The player had impressed during a loan spell with Lecce and he would go on to star at the Stadio Artemio Franchi.

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In his first two seasons, he scored 16 goals and assisted for 11 in 68 league appearances as the club finished fourth in Serie A in two successive years while playing attractive, possession-based football. His flamboyance, creativity and individual spark were pivotal to a team that won admirers for their style of play.

After a strong showing at the 2014 World Cup for Colombia, Cuadrado garnered interest from many of Europe’s top clubs. And, halfway through the 2014-15 season, he departed for Chelsea. He left having made a positive impression on Montella, who remarked: “He [Cuadrado] always demonstrated the utmost professionalism, and joy in playing. I'm happy for him, because he's gone to play in a very good team,” per FourFourTwo.

Evidently, the pair worked well together. And they could soon reunite at Milan.

There are many tactical themes that have been present throughout Montella’s coaching career thus far. One of these is his flexibility when it comes to the formation. In the past, he has used 4-3-3, 4-2-3-1, 3-4-2-1 and 3-5-2 systems, occasionally switching between shapes in the middle of games. His proclivity for tinkering in this respect is something that necessitates a degree of versatility from his players, which is where Cuadrado could bring real value.

While he could settle in comfortably on either wing of a 4-3-3, the wide man is also capable of playing in a slightly more withdrawn wing-back role as he did with Juventus. He also played as a second striker during his final six months with Fiorentina.

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Cuadrado’s ability to perform effectively in these different positions enables him to fit in to formations predicated on either a back three or a back four, something which naturally appeals to Montella as a tactician.

According to Calciomercato, the player’s agent Alessandro Lucci is currently trying to persuade Chelsea to allow his client to leave the club on loan with a right to buy. This would enable the Rossoneri to sign him, as without fresh investment the club simply could not afford to bring him in permanently this summer.

If Milan sign Cuadrado, they would be getting an experienced Serie A customer and a flexible player who can function in several different systems. They would also be signing someone who has flourished under Montella in the past, and could do so again.