Funny how money, chains and whips make me feel free
Chains = bling/jewelry, and “whips” is slang for fancy cars
Pre-emancipation proclamation, slaves were chained to allow enslavement and whipped when they misbehaved. The irony is, that these same things [in slang terms] now, make J Cole feel free.
Further irony comes from the fact that this is the opposite of what is the mindset of a slave. Whereas the money would have removed the chains chains i.e. buying their freedom, the whips and the chains would prevent them from escaping.
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