Means being in the middle of a very bad situation.
This can be a reference to Gunplay’s latest house arrest and problems with the law. Gunplay rolled with Ross even before Ross was famous so imagine how he feels.
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Slaves are held captive with chains and beaten with whips. Robb uses this as a double entendre/metaphor, as the vernacular terms ‘whips and chains’ refer to flashy cars and jewelry.
She’s enslaved when presented with this lifestyle. In other words, she’s materialistic, and possibly also a gold digger.
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I believe he’s saying he’s Wizard Kelly “Big Facing” as in counting big faces (hunnits & fifties) & these niggas still broke, & only have their pride as many broke niggas do.