Mystic Falls, 1912, Sheriff Gerald Forbes expresses concern about Mr. Zachariah Salvatore getting home safely, given the recent murder of another councilman. Mr. Salvatore rebuffs his concerns and heads out alone, and is soon stabbed in the back by an unknown attacker. 

Elena and Matt go on a run where Elena appears to be upset. Matt mentions he's talked to Bonnie and that Abby has decided to complete the transition and Caroline will be helping her adjust to her new life as a vampire. Elena feels responsible for Abby's vampirism because Damon turned her in order to save Elena's life. Elena gets a call from Liz and goes to the courthouse. Damon tells Elena he plans to stay out of it. "I'm mean, you hate me - the earth is back on its axis," he says. She tells him if he keeps pushing people away, he's going to end up alone.

Meanwhile, Damon wants to look into the murder of Zachariah in 1912, and recalls that it wasn't the first murder of a council member that year. In Damon's flashback to 1912, Stefan has returned for the man he calls his Uncle Zachariah. Marianna Lockwood introduces herself and Samantha Gilbert and they inform him Zachariah wasn't the first murder. Samantha Gilbert says it's not a good time to be a founder of the town.

Damon greets his brother. It's been 50 years since he and Stefan last saw one other. Zachariah is really their half brother. Damon is still angry at Stefan for turning him and killing their family.

Present Day Damon is determined to solve a murder and wants Stefan's help. At the Grill, Rebekah is concerned about the white ash tree, the only known tree that when wielded as a dagger can kill as original. Rebekah asks Carol about the trees in the village, as the Lockwoods used to keep those records. Damon and Stefan arrive at The Grill and Damon eyes Rebekah. Carol tells her in the old days, the Salvatore's owned all the logging mills, and would have the records.

Damon wonders what the medical examiner, Bill Forbes and Alaric have in common. Stefan is twitchy and distracted because he quit blood cold turkey. He answers the question: they're all on the council.

In lock-up, Liz Forbes lays out the case against Alaric. Meredith Fell told her Alaric saw her fight with the ME, her ex. She told him Bill threatened to report her for curing him with vampire blood. Alaric remembers they talked on the phone the night she claims, but he was drunk and doesn't remember the conversation. He has no alibi for when the ME was killed.

At The Grill, Damon explains Zachariah was the bastard son of their father, who knocked up the maid. Rebekah asks about the mills.

The murders back then were unsolved. They wonder if it was another vampire, but there weren't any circulating, except Sage. The memory takes Damon down sex memory lane.

1912 Damon and Stefan get drunk and wander into a fight in a boxing ring. A hot, red head knocks out a man and winks at Damon.

Present Day Rebekah remembers Sage as trash. Elena confronts Meredith in the parking lot. Meredith tells her Alaric was arrested four times before he was 21. Isobel took out two restraining orders against him before they married. She claims Alaric is a murderer. Rebekah tries again to ask about the Salvatore relatives cutting down trees. They brush her off.

Matt helps Elena break into Meredith's place. Elena checks the closet and finds a secret compartment, like a true founder. There are boxes of files. There are files on Brian Walters, Bill Forbes, and Alaric. Damon doesn't think a woman is capable of murdering a man. He thinks Stefan is being a wet blanket. He remembers Stefan's old sanctimony, reading from Stefan's diary to prove it. Damon remembers he was in love with Katherine, who was in a tomb. He was miserable.

1912, Sage critiques Damon's approach to feeding and tells him he should enjoy being a vampire more. She takes him back into the boxing tent. She points out the buttoned up women and tells her,they secretly want to be seduced. Sage points out Samantha.

Present Day Rebekah knew Sage. She was obsessed with Finn over 900 years ago. Damon yells at Stefan for being twitchy and makes him admit he's jonesing.

In Meredith Fell's box, they find an old Gilbert journal. A country coroner's report contradicts the ME's time of death.

They hear footsteps and hide in the closet. Meredith comes home. They wait until it's quiet and open the door. Meredith is standing outside.

At the Sheriff's office, Liz already knows the time of death of Brian Walters was wrong. Meredith brought her a letter from the coroner several hours ago and apologized for accusing an innocent man. Alaric will be released as soon as the coroner's letter is authenticated.

Stefan stalks the streets. Damon tries to find a way to help. He finds a woman on the street and compels her, then bites down. Stefan stops him. Damon presents her to him, saying he can't go from one extreme to other and has to learn how to not be controlled by blood. Stefan considers her for a moment and then bites down.

Damon stops him before he drains her, then he opens his own wrist to heal her. Matt and Elena come around the corner and sees Stefan with blood on his teeth. Elena is aghast and walks off. "So, that's gonna take a little time," Damon sums up.

Back at Elena's house, Matt doesn't understand her thing with the Salvatores. She says she felt safe with Stefan after he parents died, which she realizes sounds crazy. She knew he'd never stop loving her. He'd never die. And Damon just sort of snuck up on her. "Once you fall in love with someone, I don't know if you can ever shake them," Matt says.

Matt gives her the old Gilbert diary he swiped from Meredith. Liz didn't notice he took it. "Sometimes it pays to be the only normal one in a town of vampires, you're practically invisible," Matt says. Alaric comes home. Elena rushes to hug him.

At home, Stefan is in a mood. Damon comes home and tells Stefan he's on the road to recovery and will be the king of moderation soon. Stefan tells Damon he doesn't need his help. Damon reminds him the last time he said that, in 1912. Back at the ringside, Damon tries to convince Stefan to feed on humans. Sage reminded him how good it feels. He suggests Marianna.

Cut to Stefan chowing down on her ferociously and pushing Damon aside when he tries to stop him. He goes too far. He accidentally snaps her head clean off. Stefan runs off.

Present Day Damon reminds him by the end of the decade, Stefan was the Ripper of Monterrey. Damon didn't do anything to stop him. Stefan thinks he couldn't have. Damon said he could—he just didn't want to. He wants to now. He tells Stefan he's going to be there to help him from now on. "Because right now, you're all I've got," Damon says.

Elena reads through the old Gilbert diary. Alaric tells her he doesn't want her getting in trouble for him. She suggests they agree to take care of each other.

She thought it was Jonathan Gilbert's diary, but it turned out to be Samantha Gilbert's, his granddaughter, who went just as crazy as he did.

At the Salvatore's, Stefan has the old family archives. They got a confession in 1922, from Samantha Gilbert. They locked her up in an insane asylum. Damon finds that very weird, because he's pretty sure he had already killed her.

Meredith knocks on Alaric's door. She tells him she forged the coroner's note to clear his name so they wouldn't suspect him. She asks to come in.

Elena reads the diary, in which Samantha says she's losing time and doesn't feel like herself. Stefan thinks Samantha might be a vampire, still alive, running around killing people. Damon thinks they'd know if she was a vampire. She would have needed a ring to bring her back to life.

John Gilbert only made two. Jeremy has one. Alaric has the other. Meredith suggests Alaric might not know he's doing it. She asks if he's had any blackouts or lost time."You're insane," he says. "No, but I think you might be," she says. "You wear a ring that helps you cheat death. How many times can you die before it changes you?"

She wants to help. She tells him it happened 100 years ago. Elena comes downstairs holding the journal. "Ric, I think she's right," Elena says.

Flashback to Zachariah being stabbed in the square - by Samantha Gilbert. She's wearing the ring