Alessandro Costacurta

Alessandro Costacurta (born 24 April 1966) is an Italian football pundit, manager and former professional player who played as a centre-back.

Alessandro Costacurta was affectionally known to his fans as "Billy", due to his thin physique in his youth, and his notable skill at basketball (as the local basketball team of Milan, Olimpia Milano, was referred to as "Billy" during the late 1970s, the team's main shirt sponsor).

He is best known for his role alongside Franco Baresi, Paolo Maldini, and Mauro Tassotti, forming one of the greatest defences in Serie A and European football during the late 1980s and 1990s, under the success of managers Arrigo Sacchi and Fabio Capello.

He mainly operated as a central defender, and was a leading exponent of the position, receiving International acclaim, winning 7 Serie A titles and 5 Champions League/European Cup trophies throughout his career, along with many other trophies.

Costacurta was already a young member of the senior squad during the 1985–86 season, but failed to make a single appearance.

Throughout his club career, Costacurta spent over twenty years with AC Milan between 1986 and 2007, as well as a brief season-long spell on loan at Monza.

Originally an AC Milan youth side product, during his professional career Costacurta would go on to play for the senior club for over 20 seasons, after a brief spell on loan at Monza in Serie C1 during the 1986–87 season.

Before being sent to Monza on loan, Costacurta would make his Milan debut in the Coppa Italia during the 1986–87 season, but would not make his Serie A debut with Milan until the following year, under Arrigo Sacchi.

Costacurta made his first Serie A appearance on 25 October 1987 against Hellas Verona on the sixth matchday of the season.

Milan would go on to win the match 1–0, as well as the Serie A title, but Costacurta received limited playing opportunities that season, due to the presence of the more experienced Filippo Galli in his position.

Overall, Costacurta managed 7 appearances in Serie A, and one appearance in the Coppa Italia that season.

The 1988–89 season would see Costacurta gain more playing opportunities and appear more frequently for the club, as he would feature in Milan's 3–1 win over Sampdoria in the 1988 Supercoppa Italiana.

He would make 26 appearances in Serie A that season, and would also win his first European Cup title after Milan defeated Steaua București 4–0 at the Camp Nou, Barcelona.

Costacurta played the first 74 minutes of the final before being substituted by Filippo Galli.

During the 1989–90 Season, Costacurta won his second consecutive European Cup with Milan, defeating Benfica 1–0 in the final in Vienna, and starting the play which led to Frank Rijkaard's match-winning goal.

He also featured in Milan's Intercontinental Cup win in Tokyo over Atlético Nacional, and in the European Supercup victory over Johan Cruyff's Barcelona.

Costacurta also scored his first goal in Serie A during that season, in a 3–1 away defeat to Milanese rivals Internazionale in the Derby della Madonnina.

Milan would also reach the Coppa Italia final that season.

In Sacchi's final season at the club, Costacurta would become a starting centreback alongside Franco Baresi, as well as full-backs Mauro Tassotti and Paolo Maldini, in Sacchi's four-man defensive line, which is regarded as one of the greatest defences of all-time.

Costacurta would make 25 appearances in Serie A that season, and he would also win his second consecutive Intercontinental Cup and European Super Cup trophies.

Along with his Milan teammates, Costacurta was also an important member of the Italy national side during the 1990s.

Under Capello's Milan, Costacurta continued to be a permanent member of the starting line-up, and he won four Serie A titles (including three consecutive titles in 1991–92, 1992–93 and 1993–94, as well as another title in 1995–96), a Champions League title in 1994, an UEFA Super Cup in 1994, as well as three consecutive Italian Supercups in 1992, 1993 and 1994.

Costacurta also helped Milan to win the 1991–92 Serie A title undefeated, as Milan went on an Italian record of 58 matches unbeaten.

Milan also managed to reach three consecutive Champions League finals between 1992–93 and 1994–95.

He also played a key role in Milan's defensive line in the 1993–94 title, by only conceding 15 goals all season, as Milan finished the season with the best defence in Italy.

He made 59 appearances for Italy, scoring 2 goals, and he participated in two World Cups (in 1994 and 1998), as well as a European Championship in 1996.

With Italy, he managed to reach the 1994 World Cup Final, which was lost against Brazil on penalties.

However, Costacurta missed the 1994 Champions League final win over Barcelona on 18 May because of a suspension, having been sent-off in the semi-final match against Monaco.

Following Capello's departure after the 1995–96 title win, as well as the aging and retirement of certain key players, Milan faced dark times in their history.

Milan were defeated in the 1996 Italian Supercup final by 1995–96 Coppa Italia winners Fiorentina, and the 1996–97 and 1997–98 seasons were negative, as Milan failed to qualify for Europe on both occasions.

These fruitless seasons saw Milan undergo several managerial changes, including Tabárez, and the unsuccessful returns of Sacchi and Capello.

However, Costacurta, through his leadership in defence, would help Milan reach the 1998 Coppa Italia final, losing out to Lazio.

With the arrival of Alberto Zaccheroni during the 1998–99 season, Costacurta continued to be a key member of the starting line-up, and featured in Zaccheroni's new three-man defence alongside Maldini and Luigi Sala.

Costacurta was also named Milan's vice-captain that season, behind Maldini, following the retirement of Baresi and Tassotti.

Milan would lose the 1999 Supercoppa Italiana to Parma, and would finish in third place in 1999–2000, and in a disappointing sixth place, outside of the Champions League spots, in 2000–01.

Milan also suffered early eliminations in the first and second round of Champions League during those two seasons, and Zaccheroni would be sacked midway through the 2000–01 season, and replaced with Cesare Maldini as a temporary caretaker.

Costacurta retired from professional football at the age of 41, on 19 May 2007.

In his final match for Milan, he scored a goal from a penalty in a 3–2 defeat against Udinese, becoming the oldest goalscorer in Serie A a record that was broken by Zlatan Ibrahimović in 2023 who also scored from the spot against Udinese aged 41 five months and 15 days.

At the end of the season, Milan managed to capture their 16th Scudetto win, and Costacurta's sixth in total, finishing ahead of Lazio by a single point.

However, the next two seasons would see Milan undergo yet another trophy drought.