For decades, the title of 'Il Capitano di Milan' has referred to some of the most successful and revered players to ever don the red and black stripes. Captains from Herbert Kilpin all the way down to Gianni Rivera, for the most part, have been integral pieces to even the most successful Milan squads with their remarkable play and relentless leadership. Not only have they forged themselves into the annals of Rossoneri history, they've also forever cemented their legacies into the hearts of Milan fans with memories that can't ever be forgotten.
Franco Baresi, for one, became the most successful captain in Milan history. Paolo Maldini followed in his father's footsteps and captained the Rossoneri to two league titles, managing to carry a couple of Champions League trophies along the way. Hell, even Massimo Ambrosini got to lift a Scudetto before his tenure was up. In the case of Riccardo Montolivo, he's collected more jeers and protests than admiration from Milan fans.
Obviously an entire team's success cannot be attributed to a single person (like I said, Ambrosini got to lift a trophy), just as a club's horrific downfall cannot be blamed solely upon one individual. But with that being said, there is still an enormous difference between leading a squad with inspiring play and confidence versus being detrimental to any counter attacks and slowing offensive play down to the speed of a Sunday-league team.
Montolivo's appointment as captain came at a time where Milan was experiencing one of the more transitional periods in recent years, with some of the biggest names in Milan history departing after the 2011-12 season (Nesta, Zambrotta, Gattuso and Inzaghi). His reputation as a veteran centre-midfielder with technical ball skills and accurate passing made Montolivo a viable candidate to lead a Milan squad that was getting younger by the second. But after his devastating leg injury in 2014, Montolivo was forced to miss both the 2014 World Cup and the majority of Milan's Serie A campaign. In Montolivo's absence, Nigel De Jong unofficially assumed the captain's role and quickly became a fan-favorite in the role, reminding us all of the Gattuso-like dedication and the aggression that Milan's midfield had been lacking for quite some time.
Against popular opinion (or typical Milan fashion), Montolivo reclaimed the armband and De Jong's playing time this year under Sinisa Mihajlovic, and it has become more and more difficult to ignore the idea that Montolivo has no business being on the pitch for as long as he has been, let alone deserve to wear the captain's armband. With the uncertainty that currently surrounds the club's financial and managerial status, news of a recent three-year renewal for Montolivo seems to have added to the already large divide between Milan and its most loyal of fans, pushing some far enough to draft petitions for Montolivo's removal. Let's face it, Milan lack any sort of creativity and initiative when Montolivo is on the pitch, and with youngsters such as Jose Mauri and Gian Filippo Felicioli occupying the bench, Montolivo's renewal could also be stunting Milan's future midfield growth.
As for the captaincy, the role should be entrusted in a player who CONSISTENTLY contributes week in and week out, and confidently leads the team on an off the pitch: not one whose voice is rarely heard and whose fight is rarely seen. While Milan is still a relatively younger squad, players such as Giacomo Bonaventura and Luca Antonelli have constantly exhibited the drive and passion for Milan on both sides of the ball and have seem to win over fans in the short time they've been at Milan. Even Ignazio Abate, who came up through Milan's youth academy, has showcased his leadership on and off the pitch on several occasions and should definitely be considered for Montolivo's replacement. Milan need a captain who not only knows the way of Milan and its history, but also lives breathes and dies by the stripes on the shirt. All three have proven to be valuable assets in Milan's camp and deserve solidified spots within Milan's future.
Whether it's last season's tenth-place finish or this year's potential seventh-place finish, it's near impossible to make a case that Montolivo's return/renewal has held even a sliver of positive impact on Milan's style of play or results. Both finishes in the table hold no hope of European qualification, and unless a very favorable (and realistically unlikely) result occurs in this year's Coppa Italia Final, this season will be no different than the last. As for Riccardo Montolivo, it's looking more and more likely that the only trophies he'll be credited with lifting are those of offseason tournaments and friendly matches.