The passing of Silvio Berlusconi was announced earlier today and it has prompted a lot of reflections regarding his illustrious and successful 31-year tenure as AC Milan owner.
Berlusconi dabbled in the media industry and politics, but his name will forever be synonymous with what he did as the owner and president of Milan, his boyhood club that he bought and saved from bankruptcy in the 1980s.
He was the main man of the Rossoneri from 1986 until 2017 during which time the club won 29 trophies, going from being a debt-ridden laughing stock to a European superpower.
Those trophies included five Champions Leagues, eight Scudetto, seven Supercoppa Italiani, five European Super Cup, two Intercontinental Cups, one FIFA Club World Cup and one Coppa Italia.
Along with the trophies came so many amazing memories, goals and of course players that graced the pitch, including record-breakers and several Ballon d’Or winners.
We decided to take on the difficult task of naming the best XI of players from Berlusconi’s era.
GK: Dida
Dida arrived at Milan in 2000 and was the starter for near enough a decade, winning a Scudetto and two Champions Leagues, with the first of those coming after he saved three penalties in the 2003 final against rivals Juventus.
The Brazilian is one of four Milan keepers with 300 career appearances and he just about beats Sebastiano Rossi to be our starting goalkeeper.
RB: Cafu
Another Brazilian makes it into the line-up and this time it is Cafu, who went down as one of the first modern full-backs and someone who changed the role thanks to his attacking prowess and the ground he covered.
At Milan he won a Scudetto, the Supercoppa, one Champions League, two UEFA Super Cups and the FIFA Club World Cup, having made the move north from Roma in 2003.
CB: Alessandro Nesta
Nesta, like Cafu, made a move north from the capital in the early 2000s, but from Lazio. He is without a doubt considered one of the best defenders of all time thanks to his timing, anticipation, judgement, tackling and his distribution too.
He cost €30m but was a player Berlusconi strongly wanted. The fact he won 10 trophies in his 10-year spell – including two Scudetti and two Champions Leagues – suggests it was the right move.
CB: Franco Baresi
Not a Berlusconi signing, but Baresi is someone who became synonymous with his era. There are not enough superlatives to describe a man who spent his entire 20-year career with the Rossoneri, captaining them for 15 seasons.
At Milan hee won three UEFA Champions League titles, six Serie A titles, four Supercoppa Italiana titles, two European Super Cups and two Intercontinental Cups, becoming quite simply an icon and even having his number be retired.
LB: Paolo Maldini
Maldini made his debut as a bright-eyed teenager two years before Berlusconi bought the club, and like Baresi he spent his entire playing career with his beloved Milan, which was 25 seasons plus the captain’s arm band from 1997 onwards.
Quite simply one of the greatest defenders ever, Maldini won 26 trophies with Milan including the European Cup/UEFA Champions League five times, seven Serie A titles, one Coppa Italia, five Supercoppa Italiana titles, five UEFA Super Cups, two Intercontinental Cups and one FIFA Club World Cup.
CM: Clarence Seedorf
Seedorf’s career ran parallel to Nesta’s as he joined in 2002 and left in 2012, and he is considered to be one of the best midfielders of his generation and was given credit for modernising the role.
He remains the only player to win the Champions League with three clubs, winning nine trophies during his time at Milan, and Berlusconi even brought him back for a spell as the head coach in 2013-14.
CM: Frank Rijkaard
Rijkaard is the second of three Dutch midfielders present and former part of the ‘Tre Tulipani’ (Three Tulips) along with Ruud Gullit and Marco van Basten. He joined from Sporting CP in 1988 and went on to make 201 appearances for the club, with 26 goals and 25 assists.
The Dutchman scored the winning goal in the 1990 European Cup final against Benfica, which would be one of nine trophies he won at the club, including two Scudetto and two European Cups.
CM: Ruud Gullit
Gullit arrived a year prior to Rijkaard, joining Milan from PSV for what was then a world record transfer fee, winning the Ballon d’Or too in 1987.
He would go on to win three Serie A titles and two European Cups with Milan, amassing 171 appearances with 56 goals and 40 assists, numbers that wouldn’t be bad for a striker despite the fact he played a multitude of roles.
CAM: Kaka
Another player who needs little introduction, Kaká is widely considered one of the best players of the 2000s, having joined Milan from Sao Paolo in 2003 for an €8.5m fee that Berlusconi would go on to describe as ‘peanuts’.
The Brazilian helped Milan win the Serie A title in his first season and then he was the top scorer in the 2006–07 UEFA Champions League campaign which saw the Diavolo hoist the trophy. He wont the 2007 Ballon d’Or and ended his time at Milan with 104 goals and 81 assists in 307 games, plus five trophies.
ST: Andriy Shevchenko
Shevchenko arrived from Dynamo Kyiv for a fee of around €25m after a glowing scouting report arrived back at Milan’s headquarters. He racked up 175 goals for the Rossoneri, making him the second top scorer in the club’s history.
He also leads the Derby della Madonnina in scoring with 14 goals and he won five trophies with Milan in his seven-year first spell, with his most prestigious moment perhaps being the Ballon d’Or in 2004.
ST: Marco van Basten
Many icons of football came and went during Berlusconi’s time as Milan owner but he rarely expressed much favouritism. That lasted until an interview with Corriere dello Sport in 2020, when he named Van Basten as his favourite player.
The Dutchman scored 125 goals and added 49 assists in 201 games for Milan, who he joined from Ajax. Van Basten won the Ballon d’Or three times – in 1988, 1989 and 1992 – and he won 10 trophies with the Rossoneri.
Bench: Rossi, Tassotti, Thiago Silva, Pirlo, Gattuso, Ibrahimovic, Weah.
