text: Jay-Z by far. Diddy may be the better promoter in terms of hyping things up and relating to the people, but Jay is the better businessman. He basically owns the nets, has the Rocawear clothing line which is booming in the clothing industry, he has multi million advertising deals with Budweisier and Dell, and he is now President and CEO of Def Jam records, the biggest of all recording industrys. He has much more money and is well on his way to being the first rap billionaire, and will become this in our lifetime.