I still think that what the Crossroads Demon told Sam, about freeing Dean by killing the true contract holder, is true. Ruby is probably aware of this, but told Dean that saving him wasn't possible because the likelihood of meeting and actually killing the real contract holder is extremely small. But they'll manage it in the end, somehow. TV.
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I still think that what the Crossroads Demon told Sam, about freeing Dean by killing the true contract holder, is true. Ruby is probably aware of this, but told Dean that saving him wasn't possible because the likelihood of meeting and actually killing the real contract holder is extremely small. But they'll manage it in the end, somehow. TV.