Now that Damon (Ian Somerhalder) has his humanity turned back on, he's over the whole "servant of Satan" thing. Unfortunately, in this Vampire Diaries exclusive, it appears as though Cade (Wolé Parks) isn't quite ready to let go of his most brooding employee.

When Damon tries to quit, Cade gives him an ultimatum: "Our arrangement is very clear. Do as I say, and you won't go to hell. Disobey me, and I send you there to stay."

That's when Cade really sticks the dagger in, telling Damon he can either kill 100 evil strangers or kill Caroline Forbes (Candice King). And while we've forgiven Damon for a lot of things over the years (RIP Tyler!), we don't think there's any coming back from killing Caroline.

The Vampire Diaries airs Fridays at 8/7c on the CW.

(Full disclosure: is owned by CBS, one of the CW's parent companies.)