"Cassidy losing to Meek," now how does that look?

from Cassidy – Raid Lyrics on Rap Genius

Meaning

This is a joke/rhetorical question. Cassidy is saying he doesn’t know what it looks like for him to lose to Meek Mill in freestyles and battles since Cassidy helped teach Meek Mill develop his style. Cassidy is a more respected artist and it seems like nonsense to think Meek would ever win a beef with him.

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