Over the course of his 31-year spell in charge of Milan, Silvio Berlusconi has overseen an enormous portfolio of world class players, many of whom have been responsible for delivering one of the most successful periods in Milan’s history.
From Ruud Gullit to Kaka, the former club President brought eight Ballon d’Or winners to Milan during his reign, five of whom won the award while plying their trade at San Siro.
The list of recipients of the coveted Ballon d’Or who were signed under Berlusconi’s tenure also includes three-time winner Marco van Basten, Jean Pierre Papin the year after he won the award at Marseille, Roberto Baggio, George Weah, Rivaldo and Andriy Shevchenko.
The list of mercurial players that Berlusconi brought in during his reign is endless. Even within the three remaining years of the 1980s when the former Prime Minister took over, there had been an influx of superstar talents.
Within the first three years of his ownership, Berlusconi also brought in Roberto Donadoni, Daniele Massaro, Gullit, van Basten, Frank Rijkaard, and Carlo Ancelotti. The latter would later return to the club to win a Serie A and two Champions League titles in the mid 2000s.
The 1990s saw the arrivals of the aforementioned Papin, Weah, Baggio and Shevchenko, as well as future Champions League winners Marcel Desailly, Zvonimir Boban, Dejan Savicevic, Gennaro Gattuso and Massimo Ambrosini.
The 2000s also saw the arrivals of a phenomenal list of star signings, and within the first two years of the new millennium, Berlusconi had brought in Dida, Alessandro Nesta, Andrea Pirlo, Clarence Seedorf, Rivaldo, Filippo Inzaghi and Rui Costa, on whom he spent over €40m, the most expensive signing of his presidency.
Then in 2003 came Cafu and Kaka, Jaap Stam in 2004, as well as Ronaldo , Ronaldinho, David Beckham, Thiago Silva, Alexandre Pato and Zlatan Ibrahimovic by the time 2010 rolled around.
There were also some high profile signings after Berlusconi took over at Monza as well, bringing the likes of Mario Balotelli and Kevin-Prince Boateng.
The most recent acquisition was the signing of Matteo Pessina, who returned to his boyhood club after a six year spell away with Milan and Atalanta, a fitting way to round off Berlusconi’s transfer business.
He brought in some of the world’s best while he was there and Italy was in a position to get them.
The money dried up around 2005 and Milan were largely left to decay after that. The Pato signing didn’t work out long-term and the Ronalo/Beckham/Ronaldinho transfers were nothing but gimmicks.
Still, you could make 2 or 3 truly great teams from the players he helped sign during his era.