Jeremy attempts to broker a negotiation to end the thirty-year blood feud between Sasha and Roman. Meanwhile, Elena watches over Pack prisoner, Konstantin, who tries to deduce why she is protecting Sasha.
Newly gained artifacts take Nick and Monroe closer to the source of a long-gestating mystery. Elsewhere, Black Claw makes a deadly move that will send Portland into disarray.
Pritchard's past comes back to haunt him. 20 years ago, Pritchard covered up a murder committed by a drug lord's girlfriend, who happened to be his confidential informant at the time. Instead of staying on the right side of the law after Pritchard helped her elude the crime, 20 years later she has turned into a major drug dealer (guest star Madchen Amick). So now, Pritchard is determined to set things straight. Meanwhile, Mary's cancer is in remission but she and Otto are at odds over Pritchard, and Otto wants to find a new blood donor for her. Also, Gracie starts dating an older guy.
As a monster resembling the fabled New Jersey Devil ravages Sleepy Hollow, Crane must draw on his past to find the connection. Meanwhile, Jenny and Joe stumble as they navigate their new relationship and Abbie continues to struggle with the aftermath of her trauma.
While Stefan and Valerie search for a magical herb that can keep him hidden from Rayna, Damon comes up with his own plan to take her down for good. However, while at The Armory, Bonnie makes a shocking discovery about Rayna that brings Damon’s plan to a screeching halt. Elsewhere, a conversation with Caroline leaves Stefan questioning their future together, while Matt decides it may be time to truly take a stand against the vampires of Mystic Falls. Finally, as the season’s middle chapter draws to a close, Damon’s desire to take himself out of the game ramps up as he races to complete unfinished business with Stefan and Bonnie.