John Gilbert wasn't stupid. That was the first thing I learned in my campaign to win his trust.
The approach had to be subtle—too eager and he'd suspect manipulation, too reluctant and he'd lose interest. I needed to be exactly what he wanted to see: a grieving brother who'd lost his sister to vampires and wanted revenge but didn't know how to get it.
The opportunity came three days after the alliance meeting. John was at the Grill for a late lunch, sitting alone with a newspaper and a barely-touched salad. I stopped by his table to refill his water, lingering longer than necessary.
"Mr. Gilbert. Enjoying your visit to Mystic Falls?"
"More than I expected." He looked up with that calculating gaze I'd grown to recognize—the hunter assessing a potential asset. "How are you, Matt? I know losing your sister must have been difficult."
"It was." I let real emotion color my voice—not hard, given how often I thought about Vicki. "The police said she ran away. Drug problems, unstable home. But I know that's not what happened."
John set down his newspaper. "What do you think happened?"
"I think something in this town killed her." I glanced around the restaurant, lowered my voice. "Something the Salvatores know about. Something they're protecting."
The hook was set. I could see it in the slight shift of John's posture, the new interest in his eyes.
"That's a serious accusation."
"I've been watching them." I sat down uninvited, dropping my waiter persona for something rawer. "Stefan Salvatore started dating Elena right after Vicki disappeared. Damon Salvatore shows up whenever something strange happens. They know things. They're involved."
"You sound certain."
"I am." I met his eyes directly. "I want to know the truth about what happened to my sister. If you're here to investigate the Salvatores like the Council rumors say—I want to help."
John studied me for a long moment. I let him see the anger, the grief, the determination—all real, just aimed at different targets than he assumed.
"Meet me tomorrow night," he said finally. "The Gilbert building, eight o'clock. Come alone."
"I'll be there."
The following two weeks became a delicate dance of revelation and manipulation.
John tested me constantly. He'd drop names and watch my reactions—Stefan, Damon, Elena. He'd mention vampires and gauge whether I flinched or leaned in. He shared small pieces of information, monitoring what I did with them.
I passed every test.
Not by lying—John was too experienced to be fooled by obvious falsehood. Instead, I offered selective truths, things that aligned with his worldview while obscuring my real loyalties.
"I've been researching vervain," I told him during our third meeting. "Found some historical records about the Salvatore family. They've been in Mystic Falls since the town was founded, but there are gaps in their records. Deaths that should have ended the line, but somehow didn't."
John nodded slowly. "You've done good work. Better than most people who stumble into our world."
"Our world?"
"The supernatural world." He poured two glasses of bourbon—a ritual we'd established, mentor and student sharing drinks while discussing monsters. "The world most people refuse to believe exists. Vampires are real, Matt. They've been preying on this town for over a century."
"I knew it." I let genuine satisfaction color my voice. "I knew Vicki didn't just run away."
"She didn't." John's expression softened marginally—as much as his hardened features allowed. "I can't tell you exactly what happened to her. But I can tell you that the Salvatores are dangerous, and Founders' Day is going to change everything."
"What happens at Founders' Day?"
He considered me for a long moment, weighing risks and benefits. I held his gaze, projecting nothing but earnest hatred for vampires and desperate hunger for answers.
"We're going to clean this town," he said finally. "Permanently. I have a device—an artifact created by my ancestor—that can incapacitate vampires. At Founders' Day, we'll use it to neutralize every vampire in Mystic Falls and eliminate them."
"Every vampire? Even Stefan and Damon?"
"Especially them." John's voice hardened. "The Salvatores are at the center of everything wrong in this town. They need to be dealt with."
I nodded slowly, letting him see me processing the information. "Elena won't understand. She's... close to Stefan."
"Elena doesn't need to understand. She needs to be protected—from Stefan, from whatever influence he's exerted over her." John leaned forward. "You care about Elena too, don't you? I've seen you together."
"We grew up together. She's important to me." Not a lie. Just not the whole truth.
"Then help me protect her. Help me eliminate the vampires who've been manipulating her and everyone else in this town."
"How?"
John stood and walked to a hidden panel in the wall—a compartment I hadn't known existed in the Gilbert building's basement. He pulled out the device I'd seen at the Council meeting, brass and glass gleaming in the dim light.
"I need someone to help me set up on Founders' Day. Someone who can move through the crowd without drawing attention. Someone the vampires won't suspect." He met my eyes. "I need you, Matt."
I let a slow smile spread across my face. "I'm in."
The nights were the hardest.
Pretending to ally with John Gilbert meant suppressing every instinct that screamed warning, every moral reflex that recoiled from his casual discussion of mass murder. I'd wash dishes after our meetings, scrubbing plates with mechanical intensity, trying to process the cognitive dissonance of befriending a man I intended to betray.
Caroline helped. Not directly—she couldn't be seen near me while I was cultivating John's trust—but through coded texts and brief moments at school, reminders that I wasn't actually becoming what I pretended to be.
Still you? she'd text late at night.
Still me, I'd respond. Just tired of wearing masks.
Stefan helped too, in his own way. He understood the necessity of infiltration, the moral compromise of pretending alliance with enemies. He'd done it himself, in his long history of navigating vampire politics.
"You're doing what needs to be done," he said during one of our brief meetings. "The guilt you feel is proof that you haven't lost yourself."
Alaric was more pragmatic. "Have you found the device's location?"
"John keeps it in a hidden compartment in his car. He'll move it to the Gilbert building basement on Founders' Day morning."
"Then that's when we act." Alaric spread a schematic on the table—diagrams of the Gilbert building's floor plan, acquired through his Council connections. "If we can access the device before John activates it—"
"I can do that." I traced the route with my finger. "John's asked me to help with setup. I'll have direct access."
"Can you sabotage it without him noticing?"
"I don't know yet. I need to see the device up close, understand how it works." I looked up. "But I'll figure something out. I have to."
Three weeks until Founders' Day. Three weeks of playing the role of John Gilbert's new protégé while secretly planning his operation's destruction.
The manipulation was working. John trusted me now—or trusted me enough to share operational details he kept from most Council members. He'd revealed the device's location, the deployment timeline, the collection team assignments.
I reported everything to the alliance, building a picture of John's plan that would let us counter it when the time came.
But even as I gathered intelligence, part of me recognized the dangerous precedent I was setting. Using deception, exploiting trust, manipulating someone who—in his own twisted way—genuinely wanted to protect people from monsters.
What does it say about me that I'm so good at this?
I didn't have an answer. Maybe some questions weren't meant to be answered—just lived with.
The alliance meeting on April 5th was brief but decisive.
"John moves the device to the Gilbert building at dawn on Founders' Day," I reported. "I'll be helping with setup, which gives me access during deployment."
"Can you disable it?" Stefan asked.
"Possibly. Or I can delay activation long enough for vampires to evacuate the area." I spread my hands. "Either way, we have options now. That's more than we had three weeks ago."
Caroline squeezed my shoulder. "You've done good work."
"We've done good work." I looked around the table at my allies—a vampire, a hunter, my girlfriend, all united against a threat none of us had anticipated. "Founders' Day is in three weeks. John thinks he has a foolproof plan for vampire extermination."
I smiled, and for the first time in weeks, it felt genuine.
"He doesn't know we're already inside."
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