The attractive football and notably positive results achieved with Cagliari between 2008 and 2010 drew the attention of several major clubs to the young Italian coach, Massimiliano Allegri. After leading Sassuolo from Serie C1 to Serie B, Allegri convinced Cagliari’s president Massimo Cellino—who had previously had him as a player—to appoint him as head coach of the Sardinian club.
The gamble paid off. Despite a rough start with five consecutive defeats, Cagliari quickly climbed up the table and finished the 2008/2009 season in an impressive 9th place. That success earned Allegri the “Panchina d’Oro” (Golden Bench) award in February 2010, voted on by his fellow Serie A coaches.
In the 2009/2010 season, Cagliari dreamed of qualifying for the Europa League until February 2010. But an inexplicable collapse—just two points in eight games—led Cellino, who had also discovered Allegri had been in contact with Milan, to sack the coach in an effort to jolt the team. The dismissal came on April 13, 2010.
It was Milan CEO Adriano Galliani who had spoken with Allegri, identifying him as the ideal successor to Leonardo. Although club owner Silvio Berlusconi preferred a former Milan player for the role, Galliani convinced him. Berlusconi made a phone call to Allegri, and after Milan ended the 2009/10 season in third place, talks progressed. The agreement was formalized on June 25, 2010, following a lengthy negotiation that saw Cellino agree to release Allegri from his Cagliari contract on June 17.
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Presentation and transfer market:
Allegri was officially presented as Milan’s new coach in a press conference on July 21, 2010, the day after Berlusconi held a long, high-profile media session. “We have a group with 30-year-olds but also many young players,” Allegri said. “We have all the qualities to do well. It would be arrogant of me to come in and change everything about a team that was fighting for the title six games from the end of the last season. Leonardo and the group did good work.”
“Of course,” Allegri added, “I’ll bring in my own ideas, which differ from Leonardo and Ancelotti’s, but we shouldn’t discard what was done before—it’s a good foundation to build on.”
The summer transfer window was explosive. From Genoa came goalkeeper Marco Amelia and Greek defender Sokratis Papastathopoulos. Colombian defender Mario Yepes joined on a free from Chievo Verona. Milan also signed Ghanaian midfielder Kevin-Prince Boateng in a co-ownership deal with Genoa, and young full-back Bruno Montelongo on loan from River Plate (Uruguay).
The blockbuster arrivals came at the end of the window: Zlatan Ibrahimović joined on loan from Barcelona with a €24 million buy option, and Robinho arrived permanently from Manchester City for €18 million. They joined Brazilian stars Alexandre Pato, Thiago Silva, and (for half a season) Ronaldinho, Dutchman Clarence Seedorf, and a solid Italian core including Paolo Maldini, Christian Abbiati, Alessandro Nesta, Gennaro Gattuso, Andrea Pirlo, Massimo Ambrosini, and Gianluca Zambrotta, as pointed out by Calciomercato.
Departures included Dida and Favalli (released), Beckham and Mancini (end of loans), and on deadline day, strikers Marco Borriello and Klaas-Jan Huntelaar, along with defender Kakha Kaladze. In January, Milan added Urby Emanuelson (Ajax), Mark van Bommel (Bayern Munich), Nicola Legrottaglie (Juventus), and Antonio Cassano (Sampdoria). Ronaldinho, Paloschi, and Montelongo left during the same window.
Serie A title and Italian supercup triumph:
Milan’s new era started brightly with a 4–0 home win over Lecce on August 29, 2010 (Pato brace, Thiago Silva and Inzaghi goals). Despite a setback at Cesena in Round 2 (2–0 defeat), the team rebounded with a six-match unbeaten run (two draws, four wins). In Round 9, Juventus shocked San Siro with a 2–1 win, but Allegri’s tactical switch in the next match at Bari marked a turning point.
Ditching his favored 4-3-3 for a 4-3-1-2, Allegri deployed a muscular midfield with Boateng or Seedorf behind Pato and Ibrahimović—later replaced by Cassano after Pato’s recurring injuries. Milan won 3–2 in Bari, igniting a 7-match winning streak, including a 1–0 derby win over Inter thanks to an Ibrahimovic penalty.
Only Roma (via ex-Milan man Borriello) halted the momentum on December 18, but Milan responded with a 12-game unbeaten run starting with a 1–0 win at Cagliari (Strasser goal). Highlights included a 3–0 win over Napoli and a 1–0 win over Juventus. A 1–0 loss at Palermo in March threatened their lead, especially with Inter just two points behind, but a 3–0 derby demolition (Pato double, Cassano penalty) on April 2 crushed their rivals' hopes.
With Pirlo struggling physically, Allegri entrusted Van Bommel as the new midfield anchor. The reward came on May 7, 2011: Milan were crowned Serie A champions (18th Scudetto) with two games to spare.
However, in the Coppa Italia they fell to Palermo in the semifinals, and in the Champions League, they were eliminated by Tottenham (1–0 at San Siro, 0–0 in London).
Pirlo's departure, Beijing supercup, and decline:
The 2010/11 title, celebrated lavishly after a 4–1 win over Cagliari on May 14, ended Inter’s dominance and promised a new Milan cycle. Allegri renewed for two more years in June 2011, but Milan lost Andrea Pirlo—who left on a free for Conte’s Juventus after failing to agree on a renewal.
Despite this, Allegri won the 2011 Italian Supercup in Beijing on August 6, beating Inter 2–1 after trailing to a Sneijder free-kick. Goals from Ibrahimović and Boateng completed the comeback.
That would be the last trophy of Allegri’s first Milan tenure. In 2011/12, Barcelona knocked Milan out of the Champions League quarterfinals, and Juventus beat them in the Coppa Italia semifinals. In Serie A, Juve overtook Milan late in the season, denying them a second consecutive title.
The decline accelerated in 2012/13. Veterans Gattuso, Inzaghi, Nesta, Seedorf, Zambrotta, Van Bommel, and Roma left. Ibrahimović and Thiago Silva were sold to PSG (€21M and €42M). The signings—Constant, Montolivo, Niang, Pazzini, Muntari, El Shaarawy—couldn’t compensate.
After a poor first half of the league season, January signings Balotelli and Saponara sparked a turnaround, and Milan finished 3rd, qualifying for the Champions League. They exited the Coppa Italia to Juventus again and were thrashed 4–0 by Barcelona in the Champions League quarterfinals, overturning a 2–0 first-leg win.
Before the match, Berlusconi publicly criticized Allegri at a political event in Veneto, saying, “Allegri? He doesn’t understand s**t,” though he later backtracked. Despite the win in the first leg, Messi’s double in the return helped Barça to a 4–0 victory, souring Berlusconi further.
Berardi's poker and the sacking:
Despite mounting doubts, a dinner in June 2013 with Berlusconi and Galliani led to Allegri’s confirmation for 2013/14. But the summer weakened the squad further: Ambrosini, Boateng, Flamini, Bojan, and Antonini departed. Milan signed Matri and brought Kaká back for free. Also arriving were Poli, Valter Birsa, Bakaye Traoré, Silvestre, Vergara, and third keeper Coppola. Emanuelson and Saponara returned from loans.
It was not enough. The season began with a loss to Verona and defeats followed against Napoli, Juventus, Parma, Fiorentina, and Inter. Despite advancing to the Champions League Round of 16, domestic form was dire.
On January 12, 2014, the lowest point arrived: Milan lost 4–3 to Sassuolo, with 19-year-old Domenico Berardi scoring all four goals. Milan, 11th in the table and 20 points off the Champions League zone, were in free fall.
Allegri admitted post-match: “A strange defeat. We were 2–0 up after 12 minutes, then conceded three identical goals due to bad defending. We can’t concede four. We need to do better, especially defensively.”
Barbara Berlusconi, now vice president and CEO for the commercial sector, issued a blunt statement: “A disappointing evening—like others—which confirms the urgent need for change.”
Allegri stood by his work and deferred any decision to Galliani: “I’m calm. Everyone knows I’ll leave at the end of the season. Any earlier decision is up to the club.”
But the decision had been made. On January 13, 2014, Milan officially sacked Allegri. Mauro Tassotti took over temporarily, coaching the team in the Coppa Italia against Spezia on January 15. Clarence Seedorf was appointed the next day.
Allegri’s first Milan adventure ended after three and a half seasons, two trophies—including the club’s 18th league title—and a sacking that left a bitter taste, even for the Curva Sud, who defended him in an open letter: “We thank Allegri; the main faults lie with the club.”
Ten and a half years later, Allegri would return to that bench, lainched to greatness with Juventus, and to the fans who had always supported him.
