After Allegri, Before Pioli: A Look at Milan’s Managerial Revolving Door 

When AC Milan finally won the cherished Scudetto in the second full season of Stefano Pioli in 2022, it was met with the ultimate mix of relief with joy. 

As we all know, the Rossoneri endured a tough patch that stretched for the past decade since they last won a significant silverware (the Serie A in 2010-11 season under current Juventus manager Massimiliano Allegri).  

Countless screw-ups on the field, as well as chaos off it have contributed to their downward spiral. It also saw the resurgence of the Turin club, with La Vecchia Signora hauled nine consecutive Scudetti that was only ended by Inter’s triumph in 2021. Incidentally, five of those came to Allegri’s first stint with the Bianconeri. 

In relation to the headline, we look at how the managers that fared on the Rossoneri touchlines after the tenure of Allegri and before Pioli came to the San Siro, and how they fared right now. 

Mauro Tassotti 

The long-serving assistant took the job for just one match, and won it, in a 3-1 home win over Spezia in the Coppa Italia, just days after they sacked Allegri after their defeat to Sassuolo in league play.  

He has since returned to his assistant role and is currently without a club since January 2022 after Genoa parted company with Andriy Shevchenko. 

Clarence Seedorf 

A former Milan legend on his playing days, the Dutchman took over from Tassotti a day after their Coppa win and remained on the bench until the end of their 2014 campaign. By taking his first managerial job, he cut short his stint at Brazil’s Botafogo, ending his playing career effectively. 

He won exactly half of his 22 matches in charge of his former club, in which he was duly let go at the season’s end, following a trophyless campaign which saw their streak of European participation end as they finished eighth in Serie A.  

Seedorf later coached China’s Shenzen in 2016 and La Liga side Deportivo La Coruña, which he left the latter following their relegation to the Segunda in 2018. His most recent job came with Cameroon, where he was shown the door following their poor AFCON 2019. 

Filippo Inzaghi 

Another legend to the club was hired in 2014, and only lasted a full season before he was let go. 

Known for his scoring and striking prowess, the same could not be said of his management. Milan missed out on European football once again after finishing 10th, their worst in the Berlusconi era since their 1997-98 campaign where they end up 11th

Inzaghi later moved on from the San Siro, as he spent most of his managerial stints in the Serie B, as he was the current gaffer of Reggina. 

Siniša Mihajlović 

The Serbian took over from Inzaghi for the 2015-16 season, which was the last full campaign under the Berlusconi ownership. He had been into stints with other Italian clubs, as well as taking on the Serbian national team job, and returned to the San Siro for the first time since being the top deputy of Roberto Mancini at rivals Inter. 

Without European football, Mihajlović took the gamble in giving the starting goalkeeper job to then-16-year-old Gianluigi Donnarumma, who is a proud product of their Primavera. 

Milan started out strong, which at one point they went nine matches unbeaten and at fifth in Serie A, following key wins over Fiorentina and their derby win over Inter. However, their dream season became a horrid nightmare as a winless March led to his dismissal on April 12, three days after they lost at home to eventual league champions Juventus. 

Cristian Brocchi 

The former Rossoneri player was elevated from his job at the Primavera to save the season after the Serbian’s sacking. 

However, it was a case of too little too late as he had an even record in the last six Serie A games, as they finished seventh, four points behind Sassuolo in the final European spot. 

Brocchi’s had one final chance to get to Europe by winning the Coppa Italia against Juve. However, an extra-time strike by Alvaro Morata in the final means that they will stay home for the following season, and he was let go.  

He then managed Brescia after the Rossoneri tenure and was reunited with Berlusconi at Monza in 2018 where he oversees their promotion to Serie B, before leaving three years later a season before they finally achieved their Serie A dreams. 

He is now unattached after failing to prevent Vicenza from going down the Serie C in 2022. 

Vincenzo Montella 

He came at a time when the Rossoneri’s ownership went into foreign hands as Chinese investor Li Yonghong ended the three-decade rule of the Berlusconi and Fininvest. 

Among those managers mentioned, the Roma legend was the lone one who brought a trophy back to the San Siro, guiding them to their Supercoppa Italiana win in Qatar in December 2016 after outlasting Juve on penalties. 

In the domestic front, Montella guided them to Europe at last with a 6th place finish in the league. But he ran into trouble the following season (2017-18), with inconsistent form saw him dismissed from the job on November 27 after being held into a goalless draw by Torino in the Serie A that left the club in tenth, but not before guiding Milan to the top of their Europa League group. 

Gennaro Gattuso 

Another Milan icon took over midway into the 2018 campaign and guided them to respectability as he delivered the needed results. 

Taking over from Montella the same day he was sacked, Rino had a rough start but got hot before the new year, firing in a ten-match unbeaten run-in league play en route to a 6th place finish that made him stay until 2021. Milan also went on to the Coppa Italia final but were wiped out for four by a rampant Juve side and made the last 16 of the Europa League. 

On his lone full season in charge (2018-19), the Rossoneri were knocked out of the Europa League group stage after being pipped in the final day by Olympiacos. And by missing out on the Champions League by a point in league play, Gattuso left by mutual consent but donated his remaining wages to compensate his backroom staff. 

He then moved to Napoli where he claimed the Coppa Italia in 2020 for his first managerial silverware and is now the current boss at La Liga’s Valencia, with his 23-day stint at Fiorentina without even coaching a game in between. 

Marco Giampaolo 

The sole manager who never played in the top-flight came to Milan after prior Serie A stints with Caligiari and Empoli before getting his big break at Sampdoria, where he achieved midtable finishes at the Genoan club. 

However, his stint at the San Siro was doomed from the start, with the club being banned from European football (no thanks to the Financial Fair Play). And he only lasted just seven matches, the same number as Brocchi, before getting the boot in October despite a 2-1 away win at Genoa. 

After leaving Milan unceremoniously, he then moved to Torino before returning to Sampdoria in January 2022. 

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