Massimiliano Allegri spent his last few months with Milan as a dead man walking with rumours circulating about his imminent sack hugging the headlines of Italian newspapers day after day. The results were simply not good enough. The once mighty AC Milan was a mess on and off the pitch.
During Allegri’s reign with the Rossoneri, several players including Andrea Pirlo, Mark van Bommel, Filippo Inzaghi, Pato, Gennaro Gattuso, Massimo Ambrossini, Gianluca Zambrotta, Clarence Seedorf, Alessandro Nesta, Thiago Silva and Zlatan Ibrahimovic all left the club, be it to another club or through retirement. The players brought in to replace such an array of world-class stars were mediocre to say the least.
The club owners were hesitant to invest the necessary funds to rebuild the team and instead Allegri was given the mandate to try and develop youth players into top class stars worthy of Serie A title challengers. Mattia de Sciglio and Stephan El Sharrawy were success stories but not enough to fill such giant shoes, with the latter proving to be especially inconsistent.
Inexplicably, the owners saw fit to pay €11 for Juventus outcast Allessandro Matri in the summer of 2013 when clearly Allegri needed reinforcements in defence and midfield. A few months later, in January 2014, the former Cagliari boss was sacked with Matri soon following him through the exit doors.
His time in Milan had started well enough as he won the Serie A trophy in his first season (2010/2011). This was the Rossoneri’s first league title since 2004 and just the second Serie A trophy to be won by Milan since the turn of the millennium. However, an ageing squad meant that wholesale changes were necessary. Promises were made by Adriano Galliani and the scandal-hit Silvio Berlusconi that a new Milan was going to emerge to once more dominate Europe.
Nevertheless, Alegri was left with a squad full of mediocre players. After their title victory, Milan finished in 2nd and 3rd place with the Italian coach criticised for not mounting strong enough title challenges against the re-born Juventus.
The start to the 2013/2014 season was the final nail in the coffin for Allegri as the Rossoneri found themselves in the bottom half of the table by January.
The Livorno-born coach’s managerial career came to prominence in the 2007/2008 season when he led the small club of Sassuolo to promotion to the Serie B for the first time in their history, thus building the foundations for their eventual rise to the Serie A.