Massimo Ambrosini arrived in AC Milan in 1995. At that time, he was a young promise that started playing with top players as George Weah and Roberto Baggio, arrived in AC Milan during the same session of transfer market. His first match has been against Cagliari, when Capello was the coach, and he cooperated to the victory of the Scudetto number 15 for AC Milan, despite his young age and his limited presences on the field.

The years 1996-1998 have been characterized by a terrible injury that left Ambrosini out of the field for a long time. After this tragic moment, the midfielder restarted his career in Vicenza, that had an excellent season. In 1998 Ambrosini returned in AC Milan and the team started being coached by Zaccheroni that decided to organize a team based on young players and Ambrosini was one of them. His first important goal arrived in 1999 against Sampdoria.

The succeeding season AC Milan won Scudetto and the coach of the Italy national team decided to call him for the European Championship. His career seemed having reached the best condition when another terrible injury stopped Ambrosini, influencing also the possibilities of AC Milan in Serie A and in Europe.

Zaccheroni left AC Milan, followed by Fatih Terim and the arrival of top players as Inzaghi, Rui Costa and Pirlo. Ambrosini has never played with Terim due to his long inury. After the departure of this one and the beginning of the “Ancelotti era”, Ambrosini started playing as regular and AC Milan gained important victories: 2 Champions Leagues, Scudetto and other International Cups.

During the season 2007-2008 AC Milan started a declining phase and captain Maldini concluded his career as a player. The new captain could have been Gattuso or Abbiati, but at the end the captain became Ambrosini thanks to his ability to manage his temmates and to assure cohesion with the new arrivals. His most recent victory arrived in 2011 with the last Scudetto for AC Milan.

After 18 years, AC Milan has decided not to prolong his contract with Ambrosini and to invest in younger players. The new captain will be decided in the following weeks, but there is a bit of regret for this cold farewell by AC Milan to his important captain.