Chapter 2: A Legacy on the Line

The Caldwell estate was unnervingly quiet at night, the kind of quiet that didn’t soothe—it pressed down, like the calm before a boardroom storm. Damon walked through the study, the antique grandfather clock ticking in the corner like a metronome of judgment. His father had summoned him home hours ago, and knowing Vincent Caldwell, that never meant anything good.

The fire crackled in the hearth, throwing gold and amber shadows across the room’s mahogany walls. Vincent stood by the window, staring out over the dark lawn as if expecting some revelation to rise from the grass. Damon, still in his suit from the office, leaned against the desk.

“You said this was urgent,” Damon said, already tired.

Vincent turned. “It is. We need to talk about the clause.”

Damon rolled his eyes, muttering, “Of course we do.”

Vincent’s expression hardened. “Don’t start with the attitude. You think I enjoy reminding you? You’re the one refusing to act.”

“I’m not refusing. I’m choosing,” Damon shot back. “There’s a difference.”

“The only difference is that you're gambling your future on some philosophical nonsense,” Vincent said, voice rising. “You have five months, Damon. Five. And I’m not going to stand by and watch you throw away an empire over your ego.”

“It’s not ego. It’s principle,” Damon snapped.

“No,” Vincent countered. “It’s fear. You’re afraid of attachment, of emotion. You treat people like projections—useful or expendable. But this company needs a leader who can connect. That’s what your great-grandmother understood. That’s why the legacy clause exists.”

Damon’s fists clenched at his sides. “It’s medieval. Forcing someone to marry to inherit a company? It’s outdated.”

“Maybe,” Vincent admitted. “But it’s binding. So unless you plan to step aside and let Brayden inherit, I suggest you put on your best smile tonight and meet some very promising women. And who knows, maybe one of them will tolerate your brooding long enough to say ‘I do.’”

Damon glared. “You’ve arranged introductions?”

Vincent smirked. “It’s a fundraiser, son. Everyone’s invited. Including a very curated guest list.”

The gala was already in full swing when the Caldwells arrived. Held in the iconic Crystal Pavilion of Manhattan, the building shimmered with floor-to-ceiling glass, grand chandeliers, and floral arrangements that looked like they’d been picked from heaven’s own garden.

The fundraiser was for Project Lumen, a non-profit focused on bringing solar power to underserved regions in Sub-Saharan Africa. Damon had signed off on the sponsorship months ago without much thought. But tonight, it was his parents' playground.

Damon scanned the room. A champagne tower glittered near the stage, servers in crisp white jackets floated between guests offering hors d’oeuvres on silver trays, and a jazz trio played near the chocolate fountain. There were financiers, royalty, philanthropists, movie stars, and of course, socialites dressed like they’d stepped out of an art museum.

“Smile,” Margaret Caldwell whispered as she slipped an arm through her son’s. “You look like you’re going to a funeral.”

“I feel like I am.”

She ignored him, distracted by a passing tray of éclairs. She snatched one like a hawk. “Mm. Pistachio. Don’t let me have more than five.”

“You said that last time,” Damon muttered.

Margaret popped the éclair into her mouth and gestured grandly toward the main hall. “We’re raising funds and matchmaking. Two of my favorite hobbies.”

Damon sighed as they made their way in. His father was already shaking hands with important donors and waving toward a line of guests clearly waiting for him.

“Here we go,” Damon whispered.

The first woman was Veronica Tanaka, CEO of an AI medical diagnostics startup. She was brilliant, stunning in a crimson gown, and terrifyingly intense.

“Imagine it,” she said, leaning in. “Your logistics infrastructure combined with my real-time data analysis—we could revolutionize disaster response globally.”

“That sounds… ambitious,” Damon said.

“My therapist says I need to stop talking business on first dates,” she added with a grin. “But I told her, why waste time?”

Damon gave a polite laugh but already saw his father signaling the next introduction.

Next was Camilla Devereux, heir to a French champagne dynasty. She smelled like roses and looked like a Vogue cover, but spent ten solid minutes talking about her poodles—specifically, their dietary restrictions.

Then came Dr. Tara Ibukun, a renowned political analyst with her own TED Talk. Damon was actually intrigued—until she mentioned she only dated men who practiced transcendental meditation.

“I scream into a pillow at the gym,” Damon replied. “Does that count?”

After that came Olivia Martinez, an award-winning architect who sketched buildings on cocktail napkins between conversations. She was witty, creative, and spent most of the evening arguing with Damon about minimalist versus brutalist design philosophies.

“It’s not that I hate brutalism,” Damon said, taking a sip of wine. “I just don’t want to live inside a concrete bunker.”

“Please,” Olivia replied, eyebrow raised. “You work in one.”

Margaret, meanwhile, had already circled the snack table three times. Damon caught her trying to casually slip a cinnamon pastry into her clutch.

“Don’t look at me like that,” she said when he raised an eyebrow. “They’re tiny. Practically air.”

Elsewhere, a famous fashion designer accidentally spilled champagne on a tech billionaire’s silk tie, which led to a dramatic discussion on “texture and forgiveness.” A drunk investment banker mistook the pianist for a valet. One elderly donor tried to feed shrimp to a floral centerpiece shaped like a swan.

The absurdity of it all might have amused Damon on a different night.

But here, under the scrutiny of his father and the constant parade of potential wives, it only fueled his irritation.

By the time woman number nine began pitching a joint cryptocurrency venture built on blockchain accountability, Damon had had enough.

He stepped outside to the marble balcony, exhaling like a man breaking surface after drowning.

Vincent followed a minute later, hands clasped behind his back.

“You’re being rude,” he said.

“I’ve shaken more hands tonight than a political candidate,” Damon muttered.

“And yet you’ve shown zero genuine interest. Some of these women are extraordinary.”

“They’re also here for a company, not a connection.”

Vincent stepped closer. “What exactly are you waiting for? A lightning bolt? A soulmate? This is the real world, Damon. You need someone capable, not poetic. Someone to stand beside you, not serenade you.”

“I already have someone.”

Vincent blinked. “Excuse me?”

Damon straightened his shoulders. “I’ve been seeing someone. For a while.”

The lie came out smooth, clean. Too easy.

Vincent’s eyes narrowed. “Who?”

“She’s not… from our circle. I didn’t want to subject her to all of this until I was sure.”

His father scoffed. “You kept a relationship secret from your own family? Why?”

“Because I knew you’d react exactly like this.”

Vincent crossed his arms. “Then prove it. Bring her to brunch next weekend. I want to meet her. So does your mother.”

Damon didn’t flinch. “Fine. You’ll meet her.”

Vincent gave a satisfied nod, then turned and walked back inside.

Damon remained on the balcony, heart pounding. He had no girlfriend. No name. No plan.

But he had time.

Barely.