Just mentioning the name "Max Allegri" around a Milanista will incite some pretty strong opinions.
Allegri remains an enigma to Milan fans. He led the club to the Scudetto in his inaugural season, then finished second and third the following two seasons before getting sacked in early 2014, with the team languishing in the bottom half of the table.
In his first season Allegri had the best squad in Italy and was able to deliver a Scudetto. That team was star studded, and featured the likes of Zlatan Ibrahimovic, Thiago Silva, Alessandro Nesta, Clarence Seedorf and an inspired Robinbho. That squad, coupled with an extremely weak Serie A meant a Scudetto wasn't a pleasant surprise; it was expected, and Allegri was able to live up to expectations in his debut season.
In his second season Allegri once again had the best squad in Serie A. This time, however, Milan choked during the stretch run and coughed up the Scudetto in the final weeks to a Juventus squad with much less quality. That famous Sulley Muntari phantom goal certainly played a part in the epic collapse that cost Milan a Scudetto, but at the end of the day, it should have never been in doubt. With that squad and a weak Serie A, Allegri should have delivered a Scudetto. On too many nights it appeared that Milan didn't have a game plan. Their game plan was "give it to Zlatan and let him make magic." As Ibrahimovic went, so did Milan, and when he didn't have "it" on a given night, Allegri looked like he didn't have a plan B.
Allegri's third season may have been his most impressive. Following the summer purge that resulted in the sales of Ibrahimovic and Thiago Silva, and the contract expirations of Nesta, Gattuso, Seeforf and Filippo Inzaghi, the squad was decimated. Milan started the season in utter disarray, and if it wasn't for the heroics of Stephan El Shaarawy, the club would have been sunk by Christmas. Then, in the January window a saviour named Mario Balotelli arrived and propelled Milan into a miraculous top-three finish, realized on the final day of the season. Allegri did well to finish in the top three with a subpar squad, but make no mistake, if El Shaarawy and Balotelli were anything less than immaculate, Milan wouldn't have finished anywhere near third.
In Allegri's fourth season, the team was in utter shambles. The return of prodigal son Kaka couldn't save Milan. With El Shaarawy injured for most of the year and Balotelli unable to repeat his heroics from last season, Milan struggled mightily, and an embarrassing home loss to Sassuolo led to Allegri getting the sack.
Just like in Serie A, Allegri's results in the Champions League throughout his tenure were a mixed bag. Memorable victories like those against Arsenal and Barcelona were followed up by shambolic return legs. There was the puzzling decision to play Thiago Silva, fresh off an injury, in Serie A with a knockout game against Barcelona on the horizon. Thiago Silva re-injured himself against Roma, and missed an important fixture against Barcelona.
Allegri also made some crazy player usage decisions, like playing Urby Emanuelson, capped by the Dutch national team at left back, as a trequartista, or playing box-to-box midfielder Kevin-Prince Boateng on the wing, or converting mediocre midfielder Kevin Constant into a shambolic left back. The list goes on and on.
Allegri did some good at Milan, but at the end of the day his time had come to an end. He will continue to be a polarizing figure for Milanisti, but most would be in agreement that when Allegri was relieved of his duties, he was simply the wrong man for the job.