In summer of 2003, two relatively unknown players, Riccardo Kaka and Cristiano Ronaldo, signed for Milan and Manchester United from Sao Paolo and Sporting Lisbon respectively.
In a matter of months both became valuable assets for their new clubs.
Kaka steered Milan to the 2007 Champions League and a year later, Ronaldo helped United beat Chelsea in an unprecedented all-English final to lift their third European Cup. On a personal level, Kaka won the 2007 Golden Ball whereas Ronaldo was given the same France Football award last year.
By sheer coincidence, these two players were Real Madrid's first signings in Florentino Perez's second reign at the club this summer.
Whereas United intend utilising the proceeds made from the sale of Ronaldo (thought to be in the region of €93 million) to bolster an already-strong squad, Milan have used the €64 million cashed in on the sale of Kaka to balance their books.
This move has irked many Rossoneri supporters because the transfer of Kaka is seen as a big step in the wrong direction for a club harbouring aspirations of glory both domestically and on the continent.
In the past, Milan did lose some of their best players but stability in the team was always maintained and they went on to conquer Europe and lift the scudetto.
Marco van Basten's last competitive game for Milan was the 1993 European Cup final. The following season, Milan replaced the Dutch master by giving more playing time to veteran Daniele Massaro.
The move paid rich dividends as in 1993/94 Milan became the second Italian club - after Inter in 1964/65 - to win the scudetto and the European Cup in the same season.
More recently, in summer of 2006, Milan offloaded Andriy Shevchenko to Chelsea and in the following year they went all the way to lifting the Champions League trophy at the expense of Liverpool.
So, can history repeat itself this time around as Brazil duo Ronaldinho and Alexander Pato are now expected to be allowed a free role to operate behind a lone striker, likely to be new signing Emanuel Adebayor (Arsenal).
In other words, can Milan achieve more with less?
The answer to this depends mainly on Milan's new signings.
Ronaldinho was largely out of action for most of last season. If the 2005 Golden Ball winner can hit top-form again, the departure of Kaka could indeed pass unnoticed. Up to 2006, Ronaldinho was considered the best player in the world before hitting a dark patch with Barcelona.
Last season, Ronaldinho showed just a glimpse of his magic but to replace Kaka over an entire campaign he has to step up several gears, keep up in shape and, perhaps, earn his place back in the Brazil national team ahead of the World Cup.
New Chelsea manager Carlo Ancelotti, formerly of Milan, is doing his utmost this summer to prise Pato away from the San Siro.
However, Milan chief Adriano Galliani has insisted several times that the Brazil prodigy is not for sale.
If Pato stays put, Milan could still vie for the honours but if Milan give in to Chelsea's offers, then it becomes pretty obvious that money matters more for Galliani and the rest of the Milan hierarchy.
Pato is Milan's future. For the fans, he has become what Kaka has represented after the departure of Shevchenko.
In recent years, Milan signed seasoned players, putting commercial interests as priority ahead of football matters. But there are indications this summer that the trend is changing as Milan have already snapped up a number of promising youngsters in the shape of Ignazio Abate (Torino), Giacomo Beretta (Albinoleffe) and Gianmarco Zigoni (Treviso).
Club supremo Silvio Berlusconi was criticized in the past for having appointed novices Arrigo Sacchi and then Fabio Capello at the helm of the team. But results have always proved the Italian premier right.
Given the prevailing negative economic climate around the globe, it was inevitable not to sell Kaka at such a conspicuous transfer fee. Milan have a mammoth task in replacing the Brazil wizard but with the right moves and signings, this seemingly-insurmountable hurdle could be overcame.
It is a matter of belief.