Actually, one cannot overthink The Wire as it remains one of the most thoughtful and thought-provoking TV shows of all time. If I had to name a top five of TV shows (and I am sure I have already done this somewhere in my blog), The Wire would be number one, Mad Men and Breaking Bad would immediately follow (I liked Sopranos a lot but it was uneven and not quite as meaningful to me), and then things get confusing.
Anyhow, inspired by Bill Simmons's question to President Obama, the Grantland folks have put together a tourney bracket of The Wire: who is the greatest character of the show? Obama took the easy and obvious choice--Omar, the gay Robin Hood of the Baltimore drug wars. Of course, one could say this is a controversial pick as Omar was very violent, but he had a code--"the game is the game" and would not target folks who were not in the drug business.