Massimiliano Allegri (born 11 August 1967) is an Italian football manager and former midfielder. He was the manager of Serie A club Milan up until January of 2014. In the 2010–11 season, Allegri's Milan won their first Serie A league trophy since 2004.
After spending the earlier part of his career in the lower leagues, including his hometown club Livorno, Allegri joined Pescara in 1991. He established himself in midfield as Giovanni Galeone's side won promotion to Serie A in 1992. Allegri was an outstanding performer for Pescara in Serie A. Despite the side's relegation in last place, there was no shortage of goals and Allegri scored an impressive 12 goals from midfield. He moved on to Cagliari and then Perugia and Napoli before returning to Pescara. Brief spells at Pistoiese and Aglianese followed before his retirement from active football in 2003.
He was banned for one year in 2001 with others six Italian footballers for match-fixing following a Coppa Italia tie in 2000. The Italian Football Federation (FIGC) also handed one-year suspensions to Fabio Gallo, Sebastiano Siviglia, and Luciano Zauri of Serie A side Atalanta; and Alfredo Aglietti of Serie B's Pistoiese.
Allegri started his managerial career in 2004, serving as the boss of Serie C2 team Aglianese, the club where he spent his two final years as a player. Following an impressive season with them, Allegri was called to head Grosseto, then in Serie C1; his experience with the biancorossi, however, proved not to be as successful as with Aglianese, and he was ultimately sacked shortly after the beginning of the 2006–07 Serie C1 season. Shortly after being sacked by Grosseto, Allegri agreed to rejoin his mentor Giovanni Galeone at Udinese, becoming part of his coaching staff. This practice, however, proved to be forbidden by the Italian football laws because he was still contracted with the Tuscan club, which caused Allegri to be disqualified for three months on early 2008.
On August 2007, Allegri became head coach of ambitious Serie C1 team Sassuolo, who Allegri managed to lead quickly into the top league spots. On 27 April 2008, Sassuolo mathematically ensured the 2007–08 Serie C1/A league title, thus winning a historical first promotion to Serie B for the neroverdi.
On 29 May 2008, Allegri was announced as new head coach of Cagliari in the Serie A, replacing Davide Ballardini. Despite a disappointing start, with five losses in the first five league matches, Allegri was confirmed by club chairman Massimo Cellino and later went on to bring his team up to a mid-table placement in December. On 9 December, following a 1–0 home win to Palermo, Cagliari announced to have agreed a two-year contract extension with Allegri, with a new contract that was set to expire on 1 June 2011. The contract was then revealed to have been signed on October, in the midst of the rossoblu's early crisis result.
He completed the 2008–09 season in an impressive ninth place, which was hailed as a huge result with respect to the limited resources, the lack of top-class players, and the high quality of Cagliari's attacking football style, which led the Sardinians not far from UEFA Europa League qualification. Such results led him to be awarded the Panchina d'Oro (Golden bench), a prize awarded to the best Serie A football manager according to other managers' votes. In the 2009–10 season, he managed to confirm Cagliari's high footballing levels despite the loss of regular striker Robert Acquafresca, leading an impressive number of three players from his side — namely Davide Biondini, Federico Marchetti, and Andrea Cossu — to receive Italian national team call-ups during his reign at the club.
On 13 April 2010, Cagliari surprisingly removed Allegri from his managerial duties despite a solid 12th place with 40 points, and youth coach Giorgio Melis — with Gianluca Festa as his assistant — was appointed at his replacement.
Allegri was released from his contract by Cagliari on 17 June 2010, under request of Serie A giants Milan, who were interested in appointing him as their new manager. On 25 June, Allegri was officially appointed as the new manager of Milan. In his first season in charge, Allegri led Milan to their first championship title since 2004, beating title incumbents Internazionale in both league fixtures. His side, however, failed to make it past the semi-finals of the Coppa Italia, losing to Palermo 4–3 on aggregate. The team also qualified for the knockout stage of the UEFA Champions League, where they were eliminated by Tottenham Hotspur.
Success continued in his second season at the club. He led Milan to their sixth Supercoppa Italiana by coming from behind in a 2–1 win over city rivals Internazionale in a game played at the Beijing National Stadium. That was as far as his success went for that season, however. A semi-final Coppa Italia knockout at the hands of Juventus followed by a quarter-final UEFA Champions League knockout at the hands of Barcelona left Milan fighting on only one front towards the end of the season — the Scudetto. Even that was to be lost, however, with the Rossoneri finishing in second place to Juventus and therefore qualifying for next season's Champions League group stage.
On 13 January 2012, Allegri agreed to extend his contract with Milan to the end of 2013–14 season. On 5 June 2012, Allegri stated that he intends to coach for only 10 more years and plans to retire at the age of 55 due to the fact that coaching contains a high level of stress and anxiety. He also said that he hopes to coach the Italian national side before he retires.
At the beginning of the 2012–13 season, Milan had only collected 8 points from their first 7 games, putting Allegri in danger of getting fired early on. Despite all the criticism from the critics, Milan stuck with Allegri and he managed to get the best out of some younger players including Stephan El Shaarawy, Milan's home-grown player Mattia De Sciglio and later on Mario Balotelli. Allegri managed to steer the Rossoneri from 16th place to finishing 3rd at the end of the season, with an epic 2–1 comeback victory away to Siena. That gave Milan the spot to play in the playoff round for the 2013–14 Champions League campaign.
On 1 June 2013, club president Silvio Berlusconi confirmed Allegri to remain as the manager of Milan, despite numerous speculations that he would be given the sack. On 31 December 2013, Allegri confirmed he will leave the club at the end of the season, telling Gazzetta dello Sport that “Of course this is my last Christmas at AC Milan.”
On 13 January 2014 Milan reported that Allegri and his staff was relieved of their duties with immediate effect.