Greediest Lolcow? -

Coke Pope
Evaxephon/YanDev/Alex should be in the top IMHO. According to some estimates he has received donations that amount to 6 figures and he is using a fair amount of the cash to fuel his gambling habit while still lives with his mom and pays a couple of 'volunteers' (the people that actually do hard work) like $400 a month.
BigFazeek is a spoiled useless richfag who is both extremely greedy and extremely willing to waste massive amounts of money that he got out of his wealthy parents.
I don't know if you can consider it 'greed' but some low-effort e-beggars like Chris, Lowtax and (like you mentioned) DSP lie about what they do with the money they receive from generous orbiters or donors.
Despite his tugboat I wouldn't say that Chris is greedy like some alogs may claim, I'd say he is just too short-sided to manage it properly and he is too shameless to not beg for more. Chris is a mooch but not 'greedy' IMHO.
There is also people like Skylar Ittner, he is a middle-class brat, I wouldn't say that he is greedy, but he sees his money as a power-status thingy and he is very willing to let you know how rich he is and how much he is willing to get richer (which is not douchey but pathetic, because he is not really that resourceful to begin with)