|“||You don't know my friends...or my enemies.||”|
Throughout The Vampire Diaries SeriesInto the Wild, Damon Salvatore was also led to the island by Shane, along with Elena, Stefan, Jeremy, Bonnie, and Rebekah, and when he was off on a walk after a fight with Elena, he was attacked by Galen. Galen caught him by surprise with an arrow before tackling him. In the struggle, Damon saw the Hunter's Mark on Galen's hand, discovering he was a member of The Five. Galen managed to gain the upperhand and break Damon's neck.
In Down the Rabbit Hole, Galen Vaughn had Damon Salvatore captive, bound by vervain soaked ropes. He revealed that he had been spying on them on the island and now knew all about the Salvatore brothers and Elena. To show his dominance over Damon, he began to stab him in the neck with the end of a stick. Soon after, he took Damon through the woods, heading toward the location of the cure and explained that not long ago, presumably when Jeremy completed his Hunter's Mark, Galen's tattoo completed itself too. He then talked about how he was trying to fulfill the original mission of The Five, as made by Qetsiyah's descendants, to find, cure, and then kill Silas. When Damon questioned if Galen had been the one to kill one of the natives with a hatchet, he denied the claim and when they stumbled upon the body of Massak soon after, Galen claimed he hadn't killed him either.
Galen brought Damon to the entrance of the well where Silas was entombed to discover that Bonnie, Jeremy, and Shane had already entered. Damon broke free from his restraints and when Galen was prepared for yet another scuffle, Rebekah arrived. Well prepared to take on overwhelming odds, however, Galen was not caught off guard even knowing that only a white oak stake, which he did not have, could kill Rebekah. He settled for slowing her down, shooting her a few times before planting a stake spiked bomb on her chest. He pulled the pin, setting it off and immobilizing Rebekah as the stake shrapnel imbedded into her chest. Damon went for another attack, but was warded off quick enough that Galen pulled out one of the shotguns from his pack, which fired a vervain-laced bolas that wrapped itself around Damon's neck, tying him to a post.
Once Stefan arrived, Galen took the chance to bungee down the well, following Jeremy and Bonnie to Silas' tomb. The cure could only be moved if Silas was given blood but Jeremy was refusing Bonnie's advice to go through with it. Galen stabbed Bonnie from behind then forced his way past Jeremy and cut his own arm, attempting to raise Silas but Jeremy fought back. During their struggle, Galen reminded Jeremy that they were on the same team, berating him for wanting the cure for reasons like curing his sister. However, Katherine arrived, ready to kill Galen until Jeremy reminded her of the Hunter's Curse if she killed him so Katherine chose to knock him out instead.In Stand By Me, Rebekah and Damon were still on the island, searching for Bonnie, when Galen Vaughn attacked them, shooting Rebekah with his crossbow. When the vampires made moves to retaliate, Galen fled but was captured by Damon and Rebekah. They tied him to a tree but he didn't feel threatened, using the fact that if he died the Hunter's Curse would torment them as a defense but they told him they'd torture him over and over, taking care not to let him die. Damon realized that it couldn't be coincidence that a hunter from The Five was on the island at the same time Katherine was. Galen explained that he had learned about Silas' location from Katherine after she had found him hunting vampires in Colorado. He also let slip that Hayley was in league with Katherine. After giving up this information, Damon left and he smiled at Rebekah who picked him up, still a hostage.
In Graduation, Galen, now a ghost, showed up at Damon's house unexpectedly and shot him in the shoulder with a gun in order to get revenge on Damon for leaving him to starve to death on the island. Stefan came up behind Galen and ripped his heart out. When Vaughn woke up, Damon led him to a quarry to dig up Silas. Vaughn noticed the wound Damon's neck and figured out that Connor must have laced the bullets. Galen shot him again, this time in the leg and demanded to know where Silas is, as he knew all along that Damon was lying. When Damon falls to the floor in pain, he is shot a third time, this time in the chest before Alaric came up behind Vaughn, snapped his neck and threw his body in the quarry.
- Vaughn: "Something botherin' you?"
- Damon: "Would you believe me if I said mosquitoes?"
- Vaughn: "Aye, I would. How does it feel when a relentless eating machine is draining the blood from your veins?"
- Damon: "Itchy."
- Vaughn: "I've been killing vampires my entire life. Still, this thing refused to reveal itself to me. That was, until three days ago and it just magically completed for no apparent reason."
- Damon: "Come on, man. Do I look like I know anything about tattoos? Look at my skin. It's flawless."
- Vaughn: "Ah! You're not taking me seriously. I don't blame ya. You don't know me. So let me introduce myself. My name is Galen Vaughn, and you'd better start talkin'."
- Damon: "Mind telling me where we're going?"
- Damon: "I don't care about the cure. In fact, I don't know why anyone wouldn't want to be a vampire. You know what? If I wasn't a vampire, then I wouldn't be able to do 9 of the things I'm gonna do to you when I'm free. Make that 10."
- Vaughn: "Right."
- Damon: "All right, I admit, okay? My friends want the cure, and I want them to have it, and I get very upset when I can't provide for my loved ones. But tell me something, Vaughn, if all you're worried about is Bonnie the teenage witch, then why'd you save Jeremy and Elena yesterday?"
- Vaughn: "How did I do that?"
- Damon: "Big guy. White paint all over him. You stuck a hatchet in his spine."
- Vaughn: "I don't remember doing such a thing."
- Damon: "We're on a remote island. There's you, me, and a bunch of unpleasant locals. You expect me to believe that someone else took out that monster truck of a human being that went after Jeremy and Elena?"
- Damon: "Well, here we are. Looks like someone beat us to the punch."
- Vaughn: "That's a shame, Damon. I have no use for you anymore. Hate to kill ya."
- Damon: "Ditto. You know, that pesky hunter's curse and all. All right. How do you want to do this?"
- Vaughn: "I'll make it quick and painless."
- Damon: "Wish I could make the same promise."
- Damon: "I'm gonna kill you. And then I'm gonna get to that damn cure, and I'm gonna give it to the girl that I love."
- Vaughn: "Your attachment to your friends will be the end of you."
- Damon: "You don't know my friends......Or my enemies."
- Damon: "Mm, just the guy I wanted to see. Not really."
- Damon: "Here's the thing. I was completely willing to accept the fact that you were one man on a lonely mission to kill ol' Silas, and then I got boned by my vixen nemesis Miss Katherine Pierce, and then I start thinking there's no way that this is a coincidence. So what do you know, huh? Took you long enough."
- Rebekah: "Sorry. I had to dig the arrow out of my spine. Thank you for that."
- Damon: "Well, if you want a lead on Katherine Pierce, here's your guy."
- Vaughn: "Torture me all you want. You can't kill me. The hunter's curse will torment you forever."
- Damon: "It'll be worth it."
- Rebekah: "He's right. You can't kill him, but that doesn't mean we can't tear him apart piece by piece, nerve by nerve until the pain is so severe, that your brain shuts it off to give you one tiny moment of blessed relief, and then we'll heal you and do it again and again and again."
- Damon: "You are creepy."
- Rebekah: "Thank you."
- Vaughn: "I was tracking dens of vampires across Colorado. Katherine found me, said she could help me find Silas. She already knew about the hunter's mark, the cure."
- Rebekah: "How?"
- Vaughn: "Oh, she had someone on the inside, some werewolf girl, friends with your professor."
- Damon: "Hayley, Tyler Lockwood's old friend. Ah, I knew she was shady. Where'd Katherine find her?"
- Vaughn: "New Orleans. That's all I know."
- Damon: "Ah. Good. Let's throw him in the well. If he starves to death, it's not our fault. I'm gonna go find Bonnie."
- Vaughn: "Got a little message for you, laddie. Straight from the mouth of the witch Qetsiyah."
- Damon: "It's where I dumped Silas. Closed off to hikers, no food for animals, endlessly deep water."
- Vaughn: "I'm not following you, Damon. Where exactly did you put the body?"
- Damon: "Well, um...well, let me see. So I dragged his stone ass through here, I flung him in that general direction, then he tumbled down into those weeds...I kind of lost him in the rocks. The thing about physics...wait, what is it? It's, ah, distance equals velocity times time? Guess I should've told you to bring some scuba gear, huh?"
- Damon: "Ding-ding-ding. Not as dumb as you sound."
- Vaughn: "This was all a lie, eh? You knew you were a dead man. Well, you don't get this back. Where'd you put Silas?"
- Vaughn: "One more jolt of werewolf toxin, and you'll be dead within minutes. Where's Silas?"