Whether a scholar or a fiend, watch a pawn become a king
Someone as well off as a scholar versus someone as messed up in life as a crack fiend both have the possibility of being a pawn (relatively unimportant) or a king (successful). Plenty of college graduates end up working at crap jobs, yet Washington DC had a fiend as mayor, Marion Barry.
Cole uses chess wordplay to describe how he (like most rappers) aspires to be the future king of hip hop. Pretty sure there aren’t any aspiring rappers who are shooting for the pawn spot.
Furthermore, considering chess rules, this line is saying that Cole is doing (or trying) the impossible. (A pawn can never be promoted to a king in chess.) In this sense, it relates to the famous Chess scene from the Wire — “the King stay the King” while the pawns get taken out early.
Cole however is optimistic, implying that although he’s a pawn by currently being signed under Jay-Z at Roc Nation. one day he will be on top as a hip-hop king (with his own label/imprint).
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