Former AC Milan owner Silvio Berlusconi has admitted that he was desperate to sign Cristiano Ronaldo for the club, revealing he was keen on the forward as early as 2009.
Ronaldo enjoyed a successful career with Manchester United before leaving to join Real Madrid in 2009 for a fee of £80m, which was a world record at the time. He has since gone on to win countless trophies, including five Ballon d'Or awards, and has cemented his legacy as one of the greatest footballers of all time.
However, his career could have been incredibly different if Berlusconi had succeeded in bringing Ronaldo to Milan. According to Goal, Berlusconi was prepared to pay any price to sign Ronaldo in 2009, before the forward's blockbuster move to Real.
Berlusconi is said to have reignited his interest in Ronaldo the following year, but instead opted to sign Barcelona's Zlatan Ibrahimovic. The Swedish striker helped Milan to domestic glory, but Berlusconi remained keen on Ronaldo and even suggested to the media that the club would try and sign Ronaldo at the end of the 2010/11 season.
He said: "If we win the Scudetto, we will add one or two champions for next season, and one of those could be Ronaldo.
"And if we should add Ronaldo to our squad, I think it would make everyone happy.
"Dreams come true sometimes."
However, Milan faced financial difficulties and found themselves unable to part with the kind of money which would have been required to sign Ronaldo. Italy suffered somewhat of a financial crisis during this time, meaning Milan had no choice but to authorise the sale of Kaka to Real as they simply could not reject such a substantial offer.
Financial difficulties were not the only obstacle, as Ronaldo admitted that he was not interested in a move to Italy. When asked about a potential move to Milan in 2012, Ronaldo said: "I dream a lot, but not about football. I respect him [Berlusconi] but I want to stay here [at Real Madrid].
"The Italian league is not where I would like to play, but I respect it: there are many great champions and many great teams. In the future, nobody knows."
Six years later, Ronaldo did in fact move to the Serie A, but signed for Juventus. After a slow start to his career in Italy, Ronaldo has racked up eight goals and six assists in 14 appearances for the club, proving why Berlusconi was keen on bringing Ronaldo to Italy in the first place.