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Ruby continues on by saying, "If I told you, you two yahoos would’ve just charged after her half-cocked.
And Lilith would’ve peeled the meat from your pretty, pretty faces." Sam retorts that they're ready now.
As Dean's time is almost up and they figure out Lilith has Dean's contract, Sam wants to call Ruby for help. Sam asks Ruby if she knew Lilith had Dean's contract, and she answers yes.
Sam asks why she didn't tell him, and she responds that Sam wasn't ready.
She comes up and kills them all using her special knife.
They were initially allies against Lilith, although Sam never fully trusted her at first.
Ruby tells Sam she knows how to save Dean, but it's not her who will save him, it's Sam.