During Silvio Berlusconi’s transformative reign as AC Milan president from 1986 to 2017, the Rossoneri established themselves as a global football powerhouse. His era brought unparalleled success — 29 trophies in total, including 5 Champions League titles and 8 Serie A crowns. Berlusconi wasn’t just a president; he was a visionary who revolutionized Milan’s footballing identity and bankrolled an era filled with icons.
Here's a look at Milan’s Greatest XI under Silvio Berlusconi, a star-studded lineup that blends legendary defenders, artistic midfielders, and lethal strikers.
🧤 Goalkeeper: Dida
Dida was a key figure in Milan’s success during the 2000s. He won the UEFA Champions League twice (2003 and 2007) and was known for his shot-stopping, composure, and penalty-saving prowess. A commanding presence between the posts, Dida provided a strong foundation for Milan’s golden generation under Carlo Ancelotti.
🛡️ Defence
🔒 Right-Back: Alessandro Costacurta
Mr. Dependable. A lifelong Milanista who could play anywhere across the backline, but often deployed on the right. Costacurta's tactical intelligence and calm under pressure were crucial in multiple eras — from Sacchi and Capello to Ancelotti.
🧱 Centre-Back: Alessandro Nesta
One of the most elegant defenders the game has ever seen. Nesta arrived from Lazio in 2002 and immediately became a pillar of Ancelotti’s defence. His timing, positioning, and composure under pressure were second to none.
👑 Centre-Back: Franco Baresi (Captain)
The heartbeat of Milan. A one-club legend and arguably the greatest defender in football history. Baresi’s leadership, reading of the game, and tackling ability defined Milan’s late 80s and early 90s dominance.
🛡️ Left-Back: Paolo Maldini
The only player who could push Baresi for legendary status. Maldini’s Milan career spanned Berlusconi’s entire presidency. A left-back with the grace of a ballerina and the steel of a warrior — his leadership and consistency were world-class for over two decades.
🧠 Midfield
⚙️ Central Midfield: Frank Rijkaard
Versatile, strong, and supremely intelligent, Rijkaard was the perfect midfield anchor. He could defend, build attacks, and even score — notably the winning goal in the 1990 European Cup final.
💪 Central Midfield: Ruud Gullit
A Ballon d'Or winner who brought flair and power. Gullit was the driving force in midfield, equally adept at bossing the centre of the pitch or bursting forward into attacking areas. His influence was immense during Milan’s golden era.
🎨 Central Midfield: Clarence Seedorf
The only man to win the Champions League with three clubs — and his Milan chapter was rich with success. Intelligent, technically sound, and tactically versatile, Seedorf was pivotal in Milan’s mid-2000s European dominance.
✨ Attacking Midfield: Kaká
Pure magic in motion. Kaká’s 2007 Ballon d’Or-winning season was one of the finest seen at San Siro. With his long strides, vision, and eye for goal, he lit up Europe and was unstoppable in the 2006/07 Champions League campaign.
🎯 Attack
⚽ Striker: Marco van Basten
An artist with the boots of a killer. Van Basten scored goals of jaw-dropping beauty and devastating efficiency. Injuries cut his career short, but his impact — including two Ballon d’Ors at Milan — remains iconic.
🎯 Striker: Andriy Shevchenko
The Ukrainian sniper. With pace, movement, and lethal finishing, Sheva became one of Europe’s top forwards in the 2000s. His 2003 Champions League win and Ballon d’Or were testaments to his brilliance in red and black.
🏆 Honorable Mentions
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Sebastiano Rossi (GK) – A record-setting shot-stopper, Rossi was a key part of Milan's dominant side in the 1990s and held the Serie A clean sheet record for over two decades.
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Cafu (RB) – The Brazilian legend brought world-class energy and leadership during his time at Milan.
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Mario Tassotti (RB) – A defensive stalwart for Milan in the late '80s and early '90s, forming part of the iconic backline with Baresi, Maldini, and Costacurta.
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Thiago Silva (CB) – Elegant and composed, Thiago Silva was a leader during a transitional period for Milan.
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Andrea Pirlo (CM) – A midfield maestro, Pirlo’s vision and passing range were unmatched during his time at the San Siro.
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Roberto Donadoni (MF) – A dynamic and versatile winger, Donadoni was instrumental during Milan’s late '80s and early '90s dominance.
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George Weah (FW) – The 1995 Ballon d'Or winner blended power and skill, dazzling fans with his solo runs.
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Filippo Inzaghi (FW) – A poacher supreme, "Pippo" scored vital goals in Milan’s Champions League triumphs in 2003 and 2007.
🔚 Legacy of a Dynasty
This XI is not just a list of footballers — it’s a timeline of greatness. From Sacchi’s pressing revolution to Capello’s ruthless efficiency and Ancelotti’s tactical elegance, these players defined the Berlusconi era. More than just winners, they were artists, warriors, and icons.
Silvio Berlusconi’s Milan wasn’t just about trophies — it was about playing with style, identity, and pride. This greatest XI captures that spirit perfectly.