If you told Milan supporters before the summer that not only would they lose superstar Kaka in a sale to Real Madrid, their former hero would also be suiting up for the visitors at the San Siro only a few short months after, they probably wouldn't have believed you.
But in an ironic twist of fate, it's only fitting that European heavyweights A.C. Milan and Real Madrid will square off in group C in the first stage of this year's Champions League, along with Olympique de Marseille and FC Zurich.
Even under normal circumstances, European draws between Milan and Madrid—the two most successful clubs in the tournament's history—are enough to salivate over. But throw in the Kaka summer transfer saga and October 21 and November 3 will no doubt provide some of the most interesting moments of this season's group stage.
Despite what the two clubs have in common though, they really couldn't be further apart as far as expectations.
Real Madrid completely revamped their squad by throwing unprecedented amounts of money at the likes of Kaka, Cristiano Ronaldo, and Karim Benzema, instantly making them favourites for the title, along with defending champions Barcelona.
A.C. Milan, on the other hand, were almost non-existent in the summer transfer market, and have been struggling to deal with some traditional years since they last lifted the Champions League trophy in 2007.
After a disastrous preseason and little hope in the way of new arrivals to propel the team past their disappointing third place finish in Serie A last season, it's hard to see A.C. Milan matching the level of competition Real Madrid will bring.
So what will Milan's European adventure look like this year?
Vice-president Adriano Galliani is already starting to play down the hopes of Rossoneri fans.
"Milan was in Pot One and picked up the toughest team from Pot Two," he told Sky recently. "I would have preferred facing (Madrid) later; they have been the transfer market kings."
Getting out of the group stage is a realistic expectation, but assuming the team will struggle against Real Madrid, there will be no room for error against the lesser sides. And given the fragile confidence of this team, an upset by dark-horses Marseille might not be out of the question.
Milan's biggest troubles lie in the midfield. The aging A.C. Milan core is simply too slow to keep up with the likes of Real Madrid's Cristiano Ronaldo, Kaka, Lassana Diarra, and Xabi Alonso.
Without Kaka, Milan's hopes rely squarely on Ronaldinho's shoulders, whose critics are looking more and more correct about his declining impact on the game. Milan can no longer afford to move him to the wing either, with nobody else really capable of playing in an attacking midfield role.
Gattuso has looked even worse—a shadow of the player that shut down Cristiano Ronaldo in the 2007 Champions League semi-final. He was awful in the club's embarrassing 4-0 loss to Inter, and will need to find a way to be effective again soon if Milan has any chance at competing in the middle of the pitch.
On the wing, it's more of the same for Milan. Ambrosini is still effective in a defensive role but both he and Clarence Seedorf are starting to show their age.
Milan have finally started looking to the future by bringing back 22-year-old Ignazio Abate from loan. The promising youngster could give Milan a much needed option on the wing, but his lack of experience in Europe leaves him with a question mark.
If they have any intention on improving him, he should be playing against FC Zurich and Marseille this year.
That's not to say either of those teams won't give Milan a scare. FC Zurich are definitely the underdog of group C, but Marseille will be dangerous, despite dropping out of the group stage in the last two tournaments.
The French side, like Real Madrid (albeit on a much smaller scale), went out and improved themselves ahead of this year's Champions League. It has been 16 years since they lifted the title in 1992-1993 when they (ironically) defeated Milan in Munich.
But coach Didier Deschamps, who played in that Marseille team, has built a defensive squad that shouldn't be taken lightly and will certainly be competing for top honours in France's Ligue 1.
They spent E18 million to fill their central attacking midfield position by signing Lucho Gonzalez from Porto. That's more than Milan paid for either of their big summer signings Klass-Jan Huntelaar and Thiago Silva.
Marseille also picked up Gabriel Heinze from Madrid to play in central defense, along with defensive midfielders Edouard Cisse and Stephane Mbia.
Spaniard Fernando Morientes, who shone under Deschamps while at Monaco, was also brought in to shore up their attack.
The Rossoneri's penny-pinching this off-season certainly didn't help their cause to rebound in Europe. In fact, they might still be worse off than last season.
Without head coach Carlo Ancelotti, Kaka, or iconic defender Paolo Maldini, the lack of leadership on this Milan team is obvious. Maldini's absence has especially hurt the defensive side of their game, even with the return to form of Alessandro Nesta.
After Gattuso threw the prestigious armband to the ground after being ejected against Inter on Saturday, it's hard to say who will be able to direct Milan on the pitch when thing's aren't going their way.
But it's not all bad for new manager Leonardo, who does have four competent strikers at his disposal.
Pippo Inzaghi is one of the most dangerous forwards in Champions League history, and if the 36-year-old can find his uncanny goal-scoring touch he could be a go-to guy for Milan's European campaign. He will want to be on the pitch with Madrid legend Raul—the two iconic strikers have been battling to hold the record for most goals in European competition for two or three years.
Brazilian Alexandre Pato continues be a breath of fresh air for Milan, providing the club with what little pace they have. If the youngster can handle the extra games, Milan will need him against both Real Madrid and Marseille.
That leaves new striker Klaas Huntelaar, who has the talent to take advantage of more playing time at Milan, and Marco Borriello, who has proven to be effective in Serie A when he can stay healthy.
Unfortunately, Leonardo doesn't have much depth in other parts of the pitch, so managing his aging squad, who didn't feature at all in the Champions League last year, will be key to success.
Defensively, the combination of Silva and Nesta are proving to be a great central defensive partnership, and it might be the one area of the pitch where the Rossoneri can really outshine Madrid. A back four of Zambrotta, Nesta, Silva and either Flamini or Jankulovski is good enough to give Milan some success.
Will their legs last long enough to make respectable strides in Europe this year?
Leonardo has a lot to consider, but will need to carefully guide Milan through group C before looking too far into his Champions League future.