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What did Stringer Bell do wrong?

A great question over at Quora: What were the biggest tactical mistakes that Stringer made in Seasons 2 and 3? Why did he make these mistakes?

5. Not using a knowledgeable intermediary to deal with Sen. Clay Davis. He was clearly out of his league with Davis and had he used an attorney with the correct political connections, he could have likely gained all that he sought with fewer complications than he did.