Maddy wasn't happy.
Despite the fact that past her (the person she was before arriving in Mystic Falls) would have been thrilled to know that Elena and Stefan had now broken up, she certainly wasn't pleased with the sight of her younger brother looking so distraught all the time.
"Are you finally going to understand what I've been telling you?" she told Damon a few days later. "This weird little arrangement is going to get everyone torn apart. Katherine could kill us all in seconds if we keep making her angry. She wants Stefan alive for herself. She's leaving you alive because she knows how much conflict there is between you, Stefan, and Elena. She wants you available so that Elena can go to you and then she'll have Stefan without any problems. That poor girl's life is never going to be normal now that she got caught up in this. Maybe we should all just leave."
"We're not leaving until we find out what this bitch wants," said Damon. "I feel bad for what happened to Jenna, okay, I do. But I'm still curious. Why the moonstone? Why turn Caroline? Why did she seem okay with letting you live? Katherine hates you. You hate her. She can't be letting you live just to stay on our good side, that doesn't make sense. I have to know."
Maddy shook her head. "Curiosity killed the cat."
"Good thing I'm not a cat, then," said Damon as she walked back upstairs.
"Hey," she told Stefan, finding that he was waiting for her in her room. "Need something?"
"Just wondering the same thing he is," said Stefan, implying that he heard them. "I wanted to ask if you have any theories. You've been awfully quiet this past week."
"Jenna nearly died," said Maddy. "I only talked to her a few times, but I like her, she's nice. I don't know what Katherine's endgame is but I think the smart thing to do is skedaddle before we end up as her lunch. You know she could kill us if she wanted to. We're nothing against a five hundred year old vampire."
They heard the door opening downstairs, but ignored it, figuring Damon was just leaving. "I feel bad," said Stefan. "I do. But Katherine shouldn't get to have this much control over us. We have to stop her."
"And we will," she promised, sitting beside him. "Just... maybe not this soon. I hate seeing you so downcast, fratellino, but we have to play it smart. She's relishing in the pain you feel now that you and Elena are... you know. We have an out right now, maybe we should take it."
Stefan didn't respond. "Is that Caroline downstairs?"
Maddy frowned, listening. "Um, seems like it."
They both scurried to where Damon was offering a glass of blood to the trembling blonde.
"What happened?" asked Stefan.
"Go ahead, tell them," said Damon. "You're gonna love this."
Caroline drew a deep breath. "I saw Katherine today."
"Where?" asked Maddy.
"At the Grill. I just stopped by to gawk and... quasi-stalk Matt."
"Skip the teen drama and get to it," urged Damon.
Caroline sighed. "Then I had to pretend to use the bathroom even though I didn't really have to go because I'm a doofus. So I went into the bathroom, and I thought I saw Elena, but it was Katherine, and she told me she needed me to deliver a message."
Stefan urged her to continue. "What was the message?"
"She wants the moonstone," said Caroline. "Or she'll rip the town apart until it rains blood. Her words, not mine. She says she wants the exchange to happen tonight at the Masquerade Ball."
"Damn it," said Maddy, turning away. "She's setting it in a large gathering so that we can't do anything."
"Killing Mason threw her off guard," said Stefan.
"She's running scared," said Damon. "What she did to Jenna was desperate. She's out of tricks."
Stefan cast him a warning look. "We can't underestimate her. We have to play this smarter than her."
Caroline offered a suggestion meekly, "Can we just give her the moonstone so she'll leave?"
"No," said Damon. "Katherine's not getting dick. I've had it. I'm gonna go to the Masquerade Ball and I'm gonna kill her, tonight."
"Not alone you're not," said Maddy. "If you're going, so am I."
"Me too," said Stefan. "And I'm gonna be the one that drives a stake through her heart."
Maddy hummed. "If we're gonna do this, we need to cover all our bases. Where are we at with the Jenna situation?"
"She's getting home from the hospital today," said Caroline. "Elena and Matt are gonna go get her."
"Good," said Maddy. "Let's get to contacting everyone else so that they can be in on the plan. Minus Matt Donovan and Tyler Lockwood, obviously. They're not going to be of any use."
Damon took care of contacting Alaric, who was going to bring all the weapons he had at his disposal. Stefan texted Bonnie, while Maddy called Jeremy, giving him a choice to either join them, or keep his trap shut.
An hour later, almost everyone had arrived. Alaric had already laid out all his weapons on the dining room table, and Jeremy was going through all the fireplaces to gather spare wood.
"Hey, come on in," said Caroline, letting Bonnie in with her grimoire. Maddy looked up from the table, where Alaric was telling her the names of all his gadgets.
"This works with compressed air," said Alaric, holding up one of the pistols. "The trigger mechanism is up here. I have two of these in different sizes. For you I recommend this—" he looked at the Salvatores, sliding on a wristband with small stakes in it. "It fits nicely under the jacket sleeve. You use the trigger when you're ready." He demonstrated how it worked, throwing a punch into the air to mimic staking a vampire.
"Let's remember the most obvious issue," said Maddy. "Katherine is way older, way stronger, and unfortunately, a bit more clever because of all her experience. Damon, Stefan, and I will carry the weight of it when it comes to actual combat. But we need everyone working together and being completely focused, otherwise this isn't going to work."
They put their plan together. Alaric was going to stay with Jenna and Elena in the Gilbert House with one of the stake pistols. Everyone else would be dressed their best and attending the Masquerade Ball. Bonnie and Jeremy would find an empty room where the young witch could do a Boundary Spell that would keep the vampires in. The three Salvatores would enter willingly, and it was up to the others to lure Katherine.
"Are you sure you guys don't want me there tonight?" asked Alaric, sounding a bit worried that this might not work.
"No, I need you to stay with Elena," said Stefan. "I don't want her to know about this."
Alaric nodded. "Okay. Well, I'll make sure she doesn't leave my sight."
"Last chance," said Maddy to the group. "If anyone doesn't want to play a part in this, speak now, because once we leave to get ready at our own houses, everyone has to stick to their role. Otherwise, the entire plan will collapse and Katherine will... most likely leave our corpses in a pile and light them on fire."
"Yeah, cold feet, speak now," urged Damon. "I don't want this going wrong if someone chicken's out..." he cast the blonde a significant look. "Caroline."
"I won't," she said confidently. "Look, she killed me. Fair's fair. As long as there's no werewolf running around."
Damon flicked his hand. "Oh, I took care of Mason."
"As long as Tyler doesn't kill anyone, he won't turn," said Jeremy.
They all subconsciously turned to the Bennett witch.
"Bonnie?" asked Stefan. "Are you with us?"
She pursed her lips. "But no one gets hurt."
"If we play it right," said Maddy, "the only one getting hurt will be Katherine."
"Tonight," added Damon, "Katherine gets a stake through her heart."
They went their separate ways to get ready. Maddy settled for a short black dress with pockets, where she could easily hide a small gun with wooden bullets. She'd elected to have longer sleeves so that she could conceal the contraption Alaric had shown her earlier. It was loose enough to allow her to move easily, and despite Damon telling her to wear boots, she chose some heels with a sturdy bottom so that she wouldn't look too suspicious. She'd picked a black masquerade mask for Damon, and a reddish-black one for Stefan, fastening an emerald-black one to herself before they left the house.
"Do you see her?" asked Damon as they stood on the property, overlooking the party.
"Nope," said Stefan. "You're sure you can do this?"
Damon scoffed. "Who are you talking to?"
"Oh, I had the chance to kill her and I hesitated."
"No one is hesitating," said Maddy. "Especially not me. If either of you even start to, I'll make sure to finish the job. There will be no taking pity on that wicked little bitch." Her phone chimed. "Good, Bonnie and Jeremy are prepping the room. Let's go mingle."
She grabbed onto their arms, having them all walk down to the dance floor beneath the canopy. Stefan went off in one direction, Maddy in another, and lastly, Damon lingered behind, listening and waiting for Bonnie and Jeremy to alert them that they were ready.
Maddy tried to remain calm, but it was difficult to pretend all was well when it wasn't. She wasn't entirely sure this would work. She wished she could be more optimistic, like Stefan, instead of a major pessimist like Damon.
She danced a bit, drank, and waited until her phone buzzed, with Damon letting her know the room was ready. She made her way back to the house, walking as if she wasn't in a rush. Once inside, she found Damon by the staircase.
"Where's Stefan?" she asked.
"Not sure," Damon replied. "He might not have checked his phone yet. Come on."
They trotted upstairs and into the study that Bonnie had spelled. Once there, they received word from Stefan. Katherine was demanding the moonstone, and had just killed one of the guests as motivation for them.
"I put the body in the trunk for now," said Stefan once he finally came upstairs.
"We'll dump her when we get back," said Damon calmly.
Stefan couldn't be so calm. "This is exactly what I didn't want. Maybe we should call this off."
"We're not calling anything off!" said Maddy as she texted Jeremy, letting know his turn was up to plant a seed of doubt in Katherine's mind, urging her to go and see Caroline, who would finish luring her up.
"Yeah, Stef, this girl was just collateral damage," said Damon. "This woman ruined our lives, she destroyed us! Tonight it ends. We can do it together. I got your back. All right?"
Stefan sighed. "Alright."
They waited in the corners of the room, behind furniture so that it wouldn't be so obvious they were in there. At last, they heard voices, and caught sight of Katherine walking in, with Caroline remaining in the hallway.
"I did it," said the blonde excitedly. "I really didn't think that I'd be able to fool you but I did it!"
Katherine tried to lunge at her, but ran into the invisible barrier. "What the...?" Composing herself, she stepped back. "Stefan?"
He walked out from behind a dresser. "Hello, Katherine."
"Goodbye, Katherine," said Caroline with fake sweetness before walking away.
Katherine scoffed, looking at the stake in Stefan's hand. "You don't really think that you can kill me with that now, do you?"
"No," said Stefan as Damon emerged from behind a door holding the compressed air pistol. "But he can."
He fired before Katherine could turn around, and the stake was shot through her, just below her heart.
"And maybe I can, too," said Maddy as she and Stefan moved forward with their stakes, stabbing into her arms and shoving her into a wall.
Katherine managed to throw Stefan back, tossing him onto a table, which shattered upon impact. Maddy punched her, and one of the stakes burst out from her wrist, lodging into Katherine's throat. She ripped it out, and slashed it through the air, piercing Maddy's cheek as she kicked her back. The instant she stepped forward, Damon ripped out the stake that had impaled her, trying to stab her with it again.
This time, Katherine was ready, and she flung him into the wall, bringing several portraits down with him. Now recovered, Stefan released two mini-stakes from his wrist contraption and threw them. Katherine dodged the first, catching the second and throwing it right at Maddy, who had grabbed the compressed air pistol, and resorted to using it to whack the stake into the wall before she fired again. The stake pierced Katherine's stomach, and she stumbled, before barreling backwards and running into the wall, popping the stake right into her hand so that she could toss it at Stefan, nailing him in the leg.
Damon jumped at her right as Maddy withdrew the pistol, finding there was no way to shoot now that Damon was in the way. Katherine caught Damon's arm, breaking it and forcing it back to make him stake himself instead. Taking advantage of how focused Katherine was, Maddy and Stefan tore forward, yanking Katherine's arms behind her back and putting her in a chokehold as they slammed themselves down to the floor. Damon was just about to stake Katherine in the heart when—
"STOP!" yelled Jeremy from the doorway. "You're hurting Elena! Everything you're doing to her is hurting Elena!"
Katherine smirked, and the Salvatores had no choice but to release her.
"You think you three are the only ones with a witch on your side?" said Katherine smugly. "Wrong. And something tells me that my witch is better than your witch."
"Jeremy, go check on Elena," said Stefan. "Make sure she's okay, go!"
"Let's all make sure poor Elena is okay," said Katherine, snatching the stake from Damon's hand. "Just a little bit more pressure..." she started to cut into her palm, but Maddy slapped it out of her hands, kicking her in the abdomen and forcing her down onto the couch.
Katherine looked up at them, crossing her legs. "So, how about that moonstone?"
Maddy wanted to curse. She wanted to break something. There was no shortage of objects in the room, but she knew that taking her eyes off of Katherine for even a second would prove problematic. If she got the upper hand, she'd kill Damon without blinking.
"Madeleine, honey, you should get going," said Katherine. "Your plan didn't work. I want to talk to your brothers alone. Have it be just the three of us together, like old times. The brother who loved me too much and the one that didn't love me enough."
"And the evil bitch vampire who only loved herself," muttered Damon.
Katherine rolled her eyes. "What happened to you Damon? You used to be so sweet and polite."
"Oh, that Damon died a long time ago," he replied.
"Good," said Katherine. "He was a bore."
"Just stop talking," said Maddy, shaking her head. "Especially you, Katherine."
"I can tell the topic of conversation is making you uncomfortable," said Katherine. "We all know how much you hate anyone who has this face." She gestured to herself. "Tell me, do you think Elena enjoys having both of your brothers worship at her altar?"
Stefan forced a laugh. "That was really desperate, Katherine. Don't you think that we can see right through you?"
Katherine batted her eyelashes. "So it doesn't bother you that Damon's in love with your girlfriend?"
Stefan shook his head. "Oh, stop it."
"Or what, you'll hurt me?"
"No, because we know you'd enjoy that," said Maddy. "Why do you even want the moonstone, Katherine? What's in it for you? What did you have to gain from having Mason following you like a lost puppy?"
"Sorry about your pet wolf," said Damon snidely. "Probably should have kept him on a tighter leash."
"I'll have to remember that for next time," said Katherine. "He's not the only wolf in town."
Maddy immediately brought out her phone, telling Caroline to go and check on Tyler. "So you clearly need a wolf for something," said Maddy. "And you needed a vampire, too, otherwise, you wouldn't have turned Caroline. But what for, Katherine?"
She ignored her. "We should play charades."
Stefan switched them back to the subject at hand. "You bargained the moonstone, didn't you? When you struck a deal with George Lockwood, to help you fake your death, you told me that you gave George something that he needed. It was the moonstone, wasn't it?"
"Good for you, Stefan," said Katherine. "Two plus two... And it would have worked except that people found out that I wasn't in the tomb." She faced Damon. "Thanks to you, by the way. Have I mentioned how inconvenient your obsession with me has been?"
"You and me both, honey," muttered the elder Salvatore.
"Don't blame him for that," snapped Maddy. "You're the one that practically exploited him. You reap what you sow, Katherine. Tell us why you need the moonstone, and why you had it in the first place."
Katherine said nothing. Stefan wagged a finger. "Unless it wasn't yours to begin with. In 1864 you faked your death. Who were you running from, Katherine?"
"In 1987," she said simply, "you and Madeleine were in Chicago, at a concert of all places with that wench, Lexi."
"Excuse you," said Maddy loudly. "Don't you dare call her a—"
"Why don't you sit down and shut up, little girl?" said Katherine coldly. "The adults are talking." She shifted her gaze back to Stefan. "Come on Stefan, don't look so surprised. Of course I checked in on you over the years. You were standing in the front row, dancing all night. You were watching Bon Jovi and I was watching you."
"Who were you running from?" Stefan repeated. Katherine merely mouthed 'I love you,' at him, and smirked.
With a sigh of exasperation, Damon moved toward where a few bottles of scotch were arranged, and started to pour himself a drink in an empty glass.
"We're missing the party," said Katherine. "I'll have one of those."
"Right away Miss Katherine," said Damon mockingly before handing her a glass.
"Thank you—" Katherine had only just finished taking her first sip when Damon slammed her against the wall, popping out a stake from beneath his sleeve.
Maddy was going to let him kill her. But Stefan jumped up, pulling him off. "No, no— Damon, don't!"
"Yes, Damon, please," said Katherine, smirking maliciously.
"The second the spell is lifted, I'm gonna drive a stake right through your heart!" he snarled.
"God, you're hot," said Katherine breathily. "When did you get so hot?" She turned to the doorway, shoving Damon off when she saw a woman waiting for her.
"Katherine," said the woman, holding up the moonstone. "The spell on this room has been broken, you're free to leave."
"Thank God," said Katherine, moving closer to her. The woman didn't hand over the moonstone immediately.
"When I hand this over, my debt to you is over," she said.
"Done," replied Katherine.
Still, the moonstone didn't leave her hand. "I owe you nothing," the woman continued.
"I said done," Katherine said, a bit more harshly. "Give it."
"I wouldn't do that," said Damon. But the woman did, and Katherine took it in hand.
Instantly, she started to choke, and began to sink down to the ground. "You should have told me another witch was involved," said the woman fiercely. "She's a Bennett witch, Katherine, but I'm sure you knew that." She looked up at the Salvatores. "The spell connecting her and Elena has been broken. She'll heal quickly, Bonnie's with her. I apologize for my involvement."
They nodded gratefully at her as she walked away, leaving Katherine unconscious on the ground.