re: After rewatching The Wire, the ending for Duquan was the most depressing for me

I disagree that Namond was the "least deserving." His father was doing life in prison, and his mother essentially forced him to sling dope so she could sit out her arse, and keep up her lifestyle, and subjected him to serious mental abuse. He might have had more nice things at home than his friends, but that quality of life would only continue if he dealt drugs, as a 14 or 15 year old. You can say he was a coward, pussy, whatever, but he was really just a kid who wasn't cut out for thug life, but put on a facade because he was told that was who he was supposed to be.