"Look, the pawns, man, in the game, they get capped quick. They be out the game early. "

D' Angelo Barksdale is a primary character on The Wire. He is the lieutenant of the drug trade organization run by his uncle, Avon Barksdale, and Stringer Bell. Throughout the show, D'Angelo proves time and time again to deeply feel the polarizing effects of what, to him, is essentially "right" from "wrong."

As he watches dealers get beaten for minor infractions and is unwittingly involved in a murder, he pulls farther away from his family and the "game" itself. He is a high-ranking drug dealer with a conscience--something that doesn't generally bode well for anyone.

Eventually, D'Angelo is caught running a large amount of drugs into Baltimore and is sent to prison. Before he enters, however, he learns that his protege and friend, Wallace, has been killed by order of his uncle. This act immediately pulls the family further apart and, as D'Angelo enters prison, he feels the desire to cut ties with his family.

While in prison, D'Angelo is introduced to The Great Gatsby by F. Scott Fitzgerald and discusses it with his fellow inmates. I suggest viewing the video here.

As, Barksdale analyzes Fitzgerald's renowned novel (which was generally ignored at time of publishing...), he observes the parallels between his life and Gatsby's. D'Angelo was at the top of his game. He had money, family, a girlfriend, a son--but all of these things were meaningless to him since he earned them through a broken and damaged system. Like Gatsby, the wealth he acquired didn't negate the person he was before the money, nor did it negate the lengths they had to go through to get it. Although The Great Gatsby is sometimes viewed as an American Dream success story (individual wealth, success, etc), both Gatsby and D'Angelo prove to represent the haunting truth of that dream. Despite appearances, neither can escape who they truly are.

I believe that Adorno would say that Barksdale was only able to reach these conclusions by being necessarily excluded by the cultural majority, and therefore industry, by being imprisoned.

For some insight:

According to Wikipedia: Culture industry is a term coined by critical theorists Theodor Adorno (1903–1969) and Max Horkheimer (1895–1973), who argued...that popular culture is akin to a factory producing standardised cultural goods – through film, radio and magazines – to manipulate the masses into passivity; the easy pleasures available through consumption of popular culture make people docile and content, no matter how difficult their economic circumstances. Adorno and Horkheimer saw this mass-produced culture as a danger to the more difficult high arts. Culture industries may cultivate false needs; that is, needs created and satisfied by capitalism. True needs, in contrast, are freedom, creativity, or genuine happiness.

By those terms, Barksdale was only able to find true sense of self and insight by being faced with his most basic needs. To say that his imprisonment set him (mentally) free may sound trite, but it is true. Through the escape of his false needs perpetuated by the culture industry, D'Angelo was able to seek a different kind of freedom--freedom from the prison of his occupation and familial expectations. Neither Gatsby's nor Barksdale's stories are without tragedy. They themselves are tragic characters, unable to escape their pasts to build new futures. Through Barksdale's imprisonment, however, he is able to observe and understand more deeply the inner workings of that which actually imprisons him and, ultimately, this understanding gives him the strength to cut his familial ties and give up the drug trade.