Sam Lewis Date: 15th May 2012 at 2:31am
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It was the turn of the 21st Century. Memories of the “Grande Milan” had faded, and names like Rijkaard, Gullit, Van Basten had either moved to pastures new or retired. Milan were at a crossroads, and without serious investment –  faced a decade of mediocrity.

In light of the the mass budgets controlled by Juventus, who had bought and then sold Zinedine Zidane by this point, and building an entirely new side in the process, spending massive amounts on the likes of Lillian Thuram and Gigi Buffon, among others, or Lazio, who were in financial paradise and bought stars like Christian Vieri, Hernan Crespo and Pavel .

In swathed , who once again spent lavishly on his side, acquiring  Andrea Pirlo, Gennaro Gattuso, , Costa, Clarence Seedorf, Kaka’ and Pippo Inzaghi in the space of three seasons to add to the then record fee spent on Andriy Shevchenko in 1999. Together, with Carlo Ancelotti at the helm – Milan built an era of continued success, including two Champions League trophies in four years, and three finals.

It was a generation of players that have only now completely separated, Inzaghi’s retirement at the head of a mass exodus of players who are now Rossoneri and Calcio legends –  Nesta,  Gattuso and Seedorf all joining Alex and Marco Di Vaio on the way out of professional football.

Which leaves Milan at a similar crossroads as they were a decade ago.

Juventus are back on the their feet, the Old Lady securing a first official Scudetto in nine years, and are not looking to stop there, already promising a transfer window to bring in players of Champions League quality.

are facing a mass overhaul too, looking to bring in Equeziel Lavezzi among others to usher in a new generation of Nerrazzurro under the guidance of ambitious young manager Andrea .

With all the notable exits being the main news hanging over Via Turati, it must be the entrances that help ease the loss of nearly an entire generation of players.

A proper left back, a defensive midfielder, a creative midfielder and a natural trequartista are among the most needed in the Milan squad without even including the new holes left by the departing stars. Once again Silvio must dive into his seemingly bottomless pit of funds and create a new generation.

Names like Carlos Tevez, Wesley Sneijder have been floated about, and are quality players, but long term investments they are not. Galliani and Berlusconi would do well to focus on youth, laying foundations and building for the future. Milan have always been proud of being run like a “family”, and to replace long time heroes with quick fixes could change the layout of Milan for the worse.

Players like Paulo Ganso, Domencio Criscito, Davide and are all players that the Rossoneri have been linked with, and have already declared their interest in Milan at a prior occasion. All young, and could form the next plethora of Milanese greats.

Regardless of the targets and the funds, it is destined be a potentially defining summer for Milan. Spend well, and wisely – and Milan could continue their 21st Century success story into a new decade. Choose not to, and a few years spent watching Juventus collate another cycle of dominance may well await. The path is Berlusconi’s to take, and Milan fans better hope he picks the right one.

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