The trouble with Milan is that they're not actually very rich. Okay so they're in the Champions League consistently (although after this season perhaps not...) but that can only take you so far. They don't have the money to compete with the other two prominent leagues, the Premiership and La Liga. Notice how not too long ago there used to be live showings and highlights of Serie A games on English TV, but since Berlusconi fu**ed up and the whole match-fixing fiasco happened, they're hardly even shown anymore. Perhaps Five picked up the coverage, but then again Five pick up Everton v SK Brann so that hardly shows anything other than they're desperate (
). The point is, the HUGE value of TV money is almost entirely in La Liga (which Sky have taken to showing live) and of course the Premiership, where, say what you like about him, Scudamore has managed to haul in massive amounts of TV license money from various deals.
Other than outside investment, TV license money is pretty much the most effective way to increase income, and with no focus on Serie A anymore, the whole Italian league is suffering. Of course there are still very good teams, and I'm talking relatively - obviously AC have more money than Hereford United - but they just don't have the money to compete with the rich teams like Chelsea, Barca, Real and Manure in signing the cream of the crop, or very promising youngsters, so they're relying on the old lads who've been there to rescue the club, but as they're all knocking on abit, it's not a reliable plan.
AC Milan are in a worse position than most Serie A teams as now the majority oft heir first team is ageing and now they just don't have the money to compete with expectation and the Champions League regulars.
They need a transfer savvy manager, (Arsene Wenger would be perfect, considering he's spent so little at Arsenal) or outside investment, which itself isn't likely, as a game thats known to have been corrupt, violent and unpredictable fans that cause games to be played behind close doors, and little chance to make a profit considering lack of avenues of income doesn't sound like a sound investment to all these Americans coming over, whereas property in the Premiership, with its TV money, huge fanbase and possibility of moving up in the world (as Villa have done with Lerner) sounds like a very good buy.
So because of this, AC aren't really going anywhere, and whilst I understand Kaka is fiercely loyal, I think if he wants to achieve everything a player of his calibre should, he needs to move elsewhere, preferably abroad.