I think at the end of the day,it comes down to to his desire of CL success.Something that Milan wont target next season,but when they do get into Europe,from a completley unbiased point of view,they do bring up the strongest CL challange from Italy.
IMO,the sole reason he joined Milan was not because they were/are supposedly cleaner than Juventus..its just beacuse he wanted to play for an Italian giant that would give him the best shot at the CL in the last 4-5 years of his career.
This is where i think people are wrong. To think that with Milan the chance for winning the CL is bigger.
It's a well known fact that Milan are the most successful Italian team in Europe, but what people seem to forget that it's not the name of the team but it's a generation of players that leaves it's mark in Europe and it's very hard to create another successful generation.
To make myself more clear : Real Madrid is the team that won 9 CL's (Champion Cups) but in reality we're talking about two groups of Real Madrid players. The first one won the Cup 6 times and the second one won it 3 times.
In the meantime all the other "Real Madrid's" failed to bring the trophy to Real.
With Milan it's kinda different but still kinda same. Only the time period is different because what took Real 30 years it took only 8 years for Milan.
Milan that won 3 CL's from 1989-1994 was created by Sacchi and many players from Sacchi era were playing during the Cappelo era.
Then it took 8 years for Milan to again create a strong group that will rule Europe.
In 2003 they won the CL, they played the final in 2005 and they won it again in 2007. If you look at the team from 2003 and compare it with the team from 2007 you'll see that 7 of the players who were in the starting XI of the 2003 CL winning team were in the starting XI of the 2007 winning team (Dida, Maldini, Nesta, Gattuso, Pirlo, Seedorf, Inzaghi).
It's the same generation of players, the same coach.
This year we've seen that this group of Milan players can not go on anymore.
Milan will have to (and i think they've already started) replace many of these oldies.
Now they will have to create a new group of players. It's a long process. We're still waiting for Juve to create a new golden generation, like the one from the mid/late 90's.
Berlusconi managed to do that faster, it took him only 8 years but now it's a question how long will it take him and Milan to form a new group to rule Europe.
It won't be less than 5 years, i'm sure about that. It can be 10 years, 15 years, 20 years or 30 years like it was with Real.
Zambrotta doesn't have 30 years, 20, 10, he doesn't even have 5 years of football.
That's why i wonder if he made the right choice (if we assume that winning the CL was the reason he joined Milan).