The story of when Berlusconi wanted to sign Cristiano Ronaldo for AC Milan

It was always the former Rossoneri owner’s “dream” to bring the Portuguese superstar to San Siro but he never managed to turn it into a reality

When news of Cristiano Ronaldo’s sensational summer switch to Juventus first broke, Silvio Berlusconi admirably congratulated the Bianconeri on their remarkable coup, acknowledging that deal would benefit “the whole of Italian football.”

However, he confessed that “as a Milan fan, it will have a terrible impact.” And he didn’t just mean on the Rossoneri’s hopes of ending the Bianconeri’s run of seven successive Serie A titles. 

Ronaldo’s move to Turin came as a hammer blow to a man who had long dreamed of signing the Portuguese superstar in his former role as owner of AC Milan.

Indeed, Berlusconi became a huge admirer of Ronaldo during the forward’s days as a fleet-footed winger at Manchester United, even warning his players ahead of their 2007 Champions League semi-final first-leg trip to Old Trafford that his Rossoneri players would have to shut down “this wonderful Cristiano Ronaldo” if they were to prevail.

Ronaldo opened the scoring that night, while Wayne Rooney’s second-half double earned the hosts a dramatic 3-2 victory. 

However, Milan ultimately progressed 5-3 on aggregate, primarily thanks to Kaka, who scored twice in Manchester and once in the return fixture at San Siro. 

Berlusconi was enamoured with the idea of the Brazilian lining up in the same team as Ronaldo and it happened two years later, just not at Milan.

The former Italian Prime Minister reportedly urged Ronaldo to come to Milan after United’s 2-0 loss to Barcelona in the final of the 2009 Champions League, later claiming that he gave CEO Adriano Galliani a “blank cheque” to make it happen.

In fairness, Ronaldo was willing to leave Old Trafford but he ended up joining Kaka at Real Madrid, with Galliani tellingly admitting that the club had not been in an economic position to turn down the €67 million on offer for the Selecao star.

Even at that stage, it was clear that Milan were being affected by financial crisis starting to envelop Italy and its top teams.

However, Berlusconi refused to give up on acquiring Ronaldo. He considered making a move again in the summer of 2010 but instead opted to bring Barcelona reject Zlatan Ibrahimovic back to Serie A, initially on loan, and pair the serial Serie A winner in attack with Manchester City outcast Robinho.

The temperamental but talented duo combined to propel Milan to the title but even then, Berlusconi wasn’t satisfied.

In April 2011, before the title had been wrapped up, he revealed, “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…”

Only Berlusconi’s didn’t. 

He continued to publicly discuss the prospect of the Portugal captain playing his trade in Milan but, by April 2012, Berlusconi had accepted that he was not in a position of sufficent financial strength to make it happen.

“I would not say no [to signing him],” the media tycoon mused, “but only for a fair price due to the economic crisis that is not only in Italy.”

Another obstacle lay in the fact that, at the time, Ronaldo had no interest in playing in Serie A. 

When asked about Berlusconi’s “dream” of bringing him to Milan before a Champions League clash with CSKA Moscow, Ronaldo replied: “I dream a lot, but not about football.

“I respect him 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…”

An awful lot changed during the intervening six years and one well-managed Italian club did eventually put themselves in a position to turn the dream into a reality with a €360m package for the Portuguese.

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Sadly for Berlusconi, it was bitter rivals Juve and not his beloved Milan who finallly lured Ronaldo to Serie A this year, making the pain of missing out on the five-time Ballon d’Or winner all the more “terrible”.

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