Assessing All of AC Milan's Managers Since Massimiliano Allegri

Vincenzo Montella and Gennaro Gattuso have both had spells in charge of Milan in recent seasons
Vincenzo Montella and Gennaro Gattuso have both had spells in charge of Milan in recent seasons / Gabriele Maltinti/Getty Images
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Milan's so-called 'banter era' began with the dismissal of Massimiliano Allegri in January 2014. I Rossoneri had previously started to show signs of decline when they sold Thiago Silva and Zlatan Ibrahimovic to Paris Saint-Germain in 2012 without bringing in adequate replacements, though Allegri still managed to lead them a Champions League place in 2012/13.

They had started the following season in disastrous form, and - with little sign of improvement on the horizon - something had to change. Allegri was sacked on the 19th matchday, with Milan languishing in mid-table.

Milan haven't experienced joy like this for a while
Milan haven't experienced joy like this for a while / Giuseppe Bellini/Getty Images

It was a decision that seemed absolutely necessary at the time, but would prove to be a poor one in hindsight. Allegri subsequently led Juventus to five consecutive Scudetti between 2014 and 2019, while Milan would fail to finish above fifth in that same period.

As a result of these continual failures, Milan have had a revolving door of managers over the past six years. Here's a look at how each of these managers fared during their short tenures in charge of I Rossoneri.


Clarence Seedorf (2014)

Despite overseeing an improvement in form, Clarence Seedorf was sacked after just four months in the role
Despite overseeing an improvement in form, Clarence Seedorf was sacked after just four months in the role / Claudio Villa/Getty Images

The Milan hierarchy elected to replace their Scudetto-winning manager with Clarence Seedorf, who was seeing out his playing career in Brazil when he was offered the chance to coach the team he had made over 400 appearances for.

Thus, Seedorf announced his immediate retirement from playing and took charge of Milan. It would've been a tough job for anyone, but Seedorf managed to steady the ship, with Milan winning 11 out of their 19 remaining matches - ultimately missing out on the European places on goal difference.

Despite these promising signs, Silvio Berlusconi opted to dismiss Seedorf at the end of the season, citing that he was part of the club's "past"...which makes no sense...


Filippo Inzaghi (2014-2015)

Filippo Inzaghi's ill-fitting baseball cap has become something of a symbol of how unsuited he was to the manager's role
Filippo Inzaghi's ill-fitting baseball cap has become something of a symbol of how unsuited he was to the manager's role / ALBERTO PIZZOLI/Getty Images

In a clear sign that Berlusconi was moving on from the "past", he decided to replace Seedorf with another club legend, Filippo Inzaghi. Unlike his former teammate, Inzaghi had prior coaching experience, having previously had spells in charge of Milan's youth teams.

Despite a poor transfer window - in which the previous season's top scorer Mario Balotelli was replaced with Fernando Torres - Inzaghi's tenure began brightly, earning impressive victories against Lazio and Parma.

From there, things began to unravel. Inzaghi's Milan were utterly woeful; occupying mid-table for the majority of the season. I Rossoneri ultimately finished 10th - meaning a second-consecutive year without European football - and Inzaghi was sacked.


Sinisa Mihajlovic (2015-2016)

Sinisa Mihajlovic lasted less than in year in charge of Milan
Sinisa Mihajlovic lasted less than in year in charge of Milan / Claudio Villa/Getty Images

Sensing that the appointment of inexperienced ex-players wasn't the smartest strategy going forward, Milan opted for a more seasoned manager in the form of Sinisa Mihajlovic. The Serbian tactician had led Sampdoria to a European place the previous season - an impressive feat - so he seemed like a smart choice for I Rossoneri at the time.

Despite an underwhelming start to his tenure, Mihajlovic had Milan competing for a Europa League spot for most of the season and had overseen the emergence of a 16-year-old Gianluigi Donnarumma - who he opted to start in goal over the more experienced Diego Lopez.

A five-game winless run between February and March would prove his downfall however, and Mihajlovic was sacked with six games to go - a decision that was deeply unpopular with the Milan faithful, with 92% of them disapproving of the Serbian's dismissal.


Cristian Brocchi (2016)

Cristian Brocchi won just two of his six league games in charge
Cristian Brocchi won just two of his six league games in charge / Marco Luzzani/Getty Images

Because promoting from within worked so well last time, Berlusconi replaced Mihajlovic with Cristian Brocchi - a former Milan player who had spent the previous two years managing I Rossoneri's Primavera team.

Berlusconi got what he deserved. Brocchi won just two of Milan's remaining six league games - both of which were 1-0 victories - and Milan fell from sixth to seventh, meaning they would once again miss out on European football. Suffice to say, he was not retained for the following season.


Vincenzo Montella (2016-2017)

Vincenzo Montella won the Supercoppa Italian during his tenure at Milan
Vincenzo Montella won the Supercoppa Italian during his tenure at Milan / AK BijuRaj/Getty Images

Replacing Brocchi was Vincenzo Montella, a somewhat highly-rated manager at the time. He had successful spells as Roma's caretaker manager and with Catania, before leading Fiorentina to three consecutive fourth-place finishes.

Young, somewhat seasoned and clearly talented - his appointment seemed a sensible one, and his debut season proved that. He led Milan to sixth place and secured their first trophy in half a decade - the Supercoppa Italiana - all with minimal transfer funds. The following season, following the (ultimately doomed) takeover of Yonghong Li, he was given a large transfer kitty and, thus expectations were high.

Milan's recruited poorly, however, and Montella paid the price three months into the season. I Rossoneri were seventh at the time of his dismissal - twelve points away from the Champions League places.


Gennaro Gattuso (2017-2019)

Gennaro Gattuso led Milan to within one point of Champions League football.
Gennaro Gattuso led Milan to within one point of Champions League football. / MIGUEL MEDINA/Getty Images

Gennaro Gattuso had a lot of doubters when he was announced as Vincenzo Montella's replacement. Like Inzaghi and Brocchi, Rino was promoted from within - having been in charge of Milan's Primavera side for five months before being given the top job - so some scepticism was warranted.

It was up to Gattuso to prove his doubters wrong, and he did just that. In his debut season, Rino led Milan to the Coppa Italia final and sixth place in the league - being rewarded with a three-year contract extension. There finally seemed to be a morsel of stability at Milan and this allowed the club to finally make some progress on the pitch, as evidenced by the fact that they came within one point of Champions League football in Gattuso's second season.

So it felt like a massive step-back when Gattuso departed by mutual consent at the end of 2018/19 He is - to date - Milan's longest-serving manager since Allegri.


Marco Giampaolo (2019)

Marco Giampaolo lasted just seven games as Milan manager
Marco Giampaolo lasted just seven games as Milan manager / Tullio M. Puglia/Getty Images

Gattuso's replacement? A journeyman manager by the name of Marco Giampaolo, who had three solid, if unspectacular, seasons in charge of Sampdoria before taking charge of Milan.

It would be a understatement to suggest Giampaolo's appointment was a misguided one. He lost four - and won three - of his seven games in charge, playing some truly dire football in the process. The Milan hierarchy were quick to act and Giampaolo was axed after just three months in charge.


Stefano Pioli (2019-)

Stefano Pioli was an unpopular appointment at the time - but has so far proved his doubters wrong
Stefano Pioli was an unpopular appointment at the time - but has so far proved his doubters wrong / Marco Luzzani/Getty Images

Even before Stefano Pioli's appointment, #PioliOut was trending on Twitter. A self-confessed Interisti, Pioli had enjoyed varying degrees of success in spells with Lazio, Inter and Fiorentina, but the backlash against Pioli seemed harsh even at the time - he has a wealth of Serie A experience and was clearly a short-term option.

He has steadied the ship at Milan - having them compete for a Europa League place - something that seemed unthinkable when Giampaolo was in charge - and has recently claimed big scalps such as Lazio and Juventus.