Team captain Riccardo Montolivo is reportedly set to agree on a contract extension that will see him extend his stay with the Rossoneri until 2019. The midfielder's current deal is due to expire at the end of the current season, and on the back of his early season form, the powers that be are keen to tie him down to the club for the foreseeable future.
Signed on a pre-contract agreement from Fiorentina following a successful seven-year stint with La Viola, Montolivo would slot into the role of deep lying playmaker that Andrea Pirlo occupied prior to his departure for Juventus the year before. Montolivo's addition to the squad was intended to add the creative spark to a midfield that was all steel and no silk and provide a source of leadership following the departure of a number of key players. Things haven't really worked out that way for the former Atalanta youth product, however, and his contribution to the team over the course of the last few years has been largely underwhelming.
Despite some impressive performances in his first season, Montolivo's time with Milan has been frustrating for fans of the Rossoneri. Injury saw him miss the majority of last season, and when he did take to the field, he looked out of sorts and low on confidence. At a time when his experience and leadership were sorely needed, Montolivo continued to come up short. He was unable to influence games in the way that was expected of him, and crucially unable to fill the boots of Massimo Ambrosini, who preceded him as the team's captain. Come summer, many Milan supporters would happily have seen the club cash in on a player whose best years appeared to be behind him.
Despite interest from a handful of major European clubs, Milan opted to retain Montolivo. It would be hard to argue that it hasn't paid off to some degree at least. At last, he appears to have fully recovered from the broken leg that ended his 2014/15 season before it began, and has set about reminding us how effective he can be when he is at his best. All of Milan's best performances this season have been spearheaded by a dominant showing from Montolivo in the centre of midfield. Finally seeing game time in his preferred position in front of the defence, Montolivo has at long last begun to deliver performances reminiscent of the player who dictated the play so well at Fiorentina. His sublime pass to set up Bonaventura's goal against Udinese in September was reminiscent of Pirlo at his superlative best.
Montolivo's influence this season has been valuable, not just for his playmaking abilities, but also for his defensive contribution. His tackles and interceptions have provided much-needed protection for a fragile defence that can barely cope as it is. This area of his game has been so strong that it's called into question the place of Nigel De Jong in the team, a player who looked near untouchable at the beginning of the season. This culminated in a remarkable display against Lazio at the beginning of November, during which Montolivo ran the show from beginning to end, orchestrating arguably Milan's strongest performance of the season.
However, the flip side of this is that when Montolivo has been off this season, so have Milan. Relying on individuals is fine when you're dealing with world class talent, but for the team's performances to be so closely linked to the form of a player of Montolivo's calibre is worrisome, especially given the lack of proven alternatives. This lack of consistency calls into question whether or not Montolivo remains a sustainable long-term option for Milan in his position. With the possibility of Champions League football next season and the financial rewards that accompany it looking increasingly slim, a contract extension for Montolivo represents a significant show of faith from the club's hierarchy. In all likelihood a contract extension for Montolivo lessens the possibility of Milan adding reinforcements to the midfield in January as well, especially with the addition of the returning Kevin Prince Boateng.
The real question is, should Milan be putting all their eggs in one basket by handing Montolivo a contract extension? The club's precarious financial position is evident in the obligatory pay cut that comes with any contract extension at Milan these days, and one wonders if the money might be better saved to help invest in a player such as Axel Witsel. Whilst he may possess a slightly different skill set, he could prove a real difference-maker in a midfield that is sorely lacking a complete midfielder of his ilk, as well as a more reliable option going forward.
Whatever it may mean for the future, it's hard to argue with the level of performance Montolivo has been putting in this season, and Milanisti can only hope that he continues to do so throughout the rest of the season. It's understandable that the club don't want to risk losing him for free next year; however, despite this, it still feels as if Milan are putting all their eggs in one basket. Maybe the gamble will pay off and Montolivo will enjoy a fruitful latter period of his career as many of his contemporaries have, ideally with the help of a few reinforcements during the January transfer window. Either way though, it remains a significant gamble.