These have been a disappointing few years to forget for the red half of the San Siro, not only have AC Milan watched cross town rivals Internazionale manage to win the Serie A title back to back for the last 4 years, but they have been slowly sinking from perennial Serie A and Champions League challengers to UEFA cup participants. Yet, this summer brings the promise of much needed change as a new coach may bring new life to this dormant giant.

Many will be quick to point the finger at the ageing squad as the main cause for the stagnation of the club, and they may well have a point. The average age of AC Milan’s squad for the 2008/2009 season was just over 29, with the first XI averaging nearly 31.

Clearly Ancelotti has put his faith in the old guard over recent seasons, but now that he’s traded the red of Milan to the blue of London, his successor Leonardo, the former technical director at AC, has to revamp this old squad. Many in the Milan camp are hoping that this internal promotion yields the same success as one made last summer in Barcelona, with the promotion of one Josep Guardiola from youth team manager to first team manager.

Ancelotti wasn’t the only departure from Milan this summer, respected and loyal servant to the Rossoneri cause, Paolo Maldini, retired at the end of the 2008/2009 season, after 24 years in Milan’s first team and 31 years at the club, at the age of 40. This will leave Leonardo with the sizable task of finding a good replacement for the left back slot, or right back if he so chooses to move Zambrotta to the left side of defense, as Ancelotti has done on occasion this season.

Leonardo may have his job cut out for him as he will also have to find replacements for the Real Madrid bound Kaka, Gourcuff who’s staying in Bourdeaux and if rumours are true, the Chelsea bound Pato and Pirlo. This would mean that unlike Guardiola, who inherited a young squad that was underachieving and lacking unity under his predecessor Frank Rijkaard, Leonardo’s success will hinge on some key transfers.

However, to look on the bright side, Milan do have some promising younger players already at the club. Felipe Mattioni, the 20 year old Brazilian with Italian citizenship may not be quite ready next season, but looks set for a promising career and his fellow countryman Thiago Silva, 24 year old Brazil international from Fluminese, is set to be registered with the club since his arrival in December. Marco Boriello, the 26 year old former Milan trainee, is set to play a bigger role, along with diminutive Uruguayan wonderkid, Tabare Viudez, up front should Pato join Ancelotti at the Bridge.

Yet what this season has proved if anything is Milan’s deficiencies against the smaller teams dropping points against the likes of 17th placed Bologna and bottom of the table Lecce, forcing them to secure Champions League football only on the final day of the season. So what does this mean for Leonardo Surely this is not the problem of on-field leadership as he has more leaders at his disposal than any other household European club. Perhaps it is the lack of hunger in ageing players; perhaps it is Ancelotti’s constant focus on European football, as evidenced by his 2 Champions League trophies compared to his solitary Serie A title in his eight years in charge of the rossoneri; perhaps it is the lack of out and out wingers in the squad that has lost the roving wing backs Cafu and Serginho to age.

However Leonardo chooses to proceed in the transfer market this summer will say a lot about how he plans to reshape a team that will definitely lose its storied captain and probably lose its attacking core of Kaka, Pirlo and Pato to richer pastures in foreign lands, but with the return to Champions League football, this once proud giant of European football is back on it’s feet for now.