Other than Omar, Stringer was always my favorite character. I just loved how they presented him as being so rational. He's a business man, and like so many "legitimate" businessmen, he was willing to do what it took to win. Only difference between him an other guys was that his business was underground.
re: the OP - I'm assuming that you're saying Hillary is a Carcetti character? I don't remember Carcetti's history well enough to know what they have in common. All I really remember about him is that he was a liar and a cheater, but that's true of pretty much everyone in politics...