Chapter 2
James
Whiskey Locker provided the best Friday happy hour in all of New York City.
Everyone from Wall Street would migrate from the southern tip of Manhattan up toward Central Park to loosen their ties, leaving behind the high-rise offices full of people dealing with the cash flow of the wealthiest people around the world.
This bar drew nearly every crowd in New York—models within the fashion industry, Wall Street mongers, celebrities, musicians, influencers—you name it.
They lounged around the dimly lit velvet booths that provided privacy for its patrons.
But a crowd like that always drew in curious onlookers, those that wanted to breathe the same air as those with the power to influence industries.
Men and women leaned against the bar, hoping for someone sitting in those booths to pluck them out of anonymity and deem them worthy of their time and energy.
But despite the various groups mingling together, there was one profession that had always reigned supreme at Whiskey Locker.
They were unmistakable—the tailored suits, perfectly pressed vests, and glinting luxury watches set them apart.
These were the investment bankers, financial analysts, hedge fund managers, and everything in between—the true backbone of this establishment.
Or what social media now kindly referred to as “finance bros”.
The bar had always belonged to them—to us. And I was proud of it.
“Are you going over to Michelle and Elliot’s for dinner tonight?” Sebastian, my best friend and heir to Whittaker Holdings—the biggest fashion conglomerate on the planet—asked me.
“I was planning on it,” I told him as I tapped my ring inscribed with my family’s crest against my whiskey glass. “Are you?”
Sebastian shook his head. “Not tonight. I have a meeting with an upcoming designer. I’m hoping to close a deal with her tonight.”
“Business or pleasure?” I gave Seb a knowing smirk as I took a sip.
Sebastian Whittaker was many things—a fiercely loyal friend, a business shark, and an exceptional flirt.
It wasn’t unheard of for him to mix the latter two for his own personal means.
He’d been tossing ethics out the window since I met him back at Princeton, a true hedonist at heart.
But that didn’t mean he wouldn’t earn the title of CEO of Whittaker Holdings when it was time for him to take over the company from his father.
Of course, there were always whispers—the “nepo baby” allegations followed him wherever he went as people watched him play the charming playboy.
They liked to call him a product of privilege, a rich kid who had coasted through life on his father’s name.
But anyone who knew him, anyone who had watched him put in the long nights and fight for his place in the cutthroat world of business, knew that Sebastian had earned everything that came to him.
“Business. Strictly business on this one.” Seb smoothed a hand over his dark hair, the tattoos on his hands stretching. “Elliot wasn’t happy to hear I’d be missing out again tonight. He told me he was going to leave me off the invite list if I didn’t make it to the next one.”
“You know how Elliot gets,” I told him. “He doesn’t want to feel like his relationships are purely ornamental. And he’s not wrong. You haven’t made as much of an effort lately to show up to things.”
“I’ve been busy.” A muscle flexed in Seb’s jaw. I knew that he’d had an enormous amount of pressure on him as he prepared to take the helm of his family’s company, but he never shared enough for me to know where his head was at.
“Right.”
Elliot Granger was the last piece that completed our Princeton trio.
The three of us had been inseparable in college.
We couldn’t be more different. While Sebastian partied almost constantly and I networked to climb the Wall Street ladder before graduation, Elliot secluded himself in his apartment to learn about the cryptocurrency market.
By the young age of twenty-two, he’d become one of the most successful cryptocurrency wallet managers in the world, changing the game for hedge fund managers forever.
He was on track to be one of the youngest billionaires in the world.
Between all of that, I’m still not sure how he snagged Michelle during our time at Princeton.
She was effortlessly beautiful, with a sharp mind to match, and always had a way to make everyone around her feel like they were the most important person in the room.
Elliott was a goner the second he laid eyes on her.
My phone chimed with another automated email analysing today’s market. Ignoring the sigh from Seb across from me, I reached for it.
“You could use a little less business and a bit more pleasure, I think.”
With a final sip of my whiskey, I declined.
“It’s been over a year since Cassidy, man. You haven’t even spared a glance at another woman.”
“And I don’t plan to anytime soon.”
At one time, I had thought Cassidy Lark was the love of my life.
From the first moment I spotted her working behind the counter of my favorite coffee shop, her energy had enraptured me.
She’d been so charismatic, so magnetic, so completely different from every girl that I’d grown up with, that I’d fallen head over heels.
I had thought I’d found the love my parents had—strong enough to conquer even the deep lines between social classes.
That was, until I’d stumbled across the thousands of dollars she’d siphoned off me over the course of our relationship and the entire thing came crashing down.
“You’re going to have to, eventually.” What I loved about Sebastian was his stubborn persistence until it was directed at me.
“Who says?”
“I know you, James.” Sebastian leveled me with a look, his gray eyes narrowed. “You crave that kind of connection. If you don’t seek it out, it’s going to find you.”
“We’ll see about that.” I tossed a hundred dollars down on the table to cover our drinks and a tip. “Have fun tonight.”
“Always do.”
I paused in the hallway when I heard shouting on the other side of my parents’ apartment door.
What the fuck?
The pounding of my fist echoed off the marble in the entryway foyer of their penthouse apartment on the Upper East Side.
Their building’s grand windows overlooked Central Park.
When I was a kid, I sometimes forgot I lived in a concrete jungle with that view.
The soft hum of traffic from below barely pierced the thick walls of their upscale, meticulously decorated home.
Shuffling and faint shouts came from the other side, then the door opened to reveal my mother—Eloise Rossi.
She was dressed in luxuriously simple cashmere, the kind that only a few select designers ever seemed to get right, paired with silk lounge pants.
Her blonde hair was styled in a French twist, and her makeup was impeccable, not a blemish in sight.
Although I got her blue eyes and high cheekbones, my dark hair and thick eyebrows came from my father’s Italian ancestry.
I wrapped my arms around my mother’s petite frame, the familiar scent of her perfume grounding me. The warmth of the hug was comforting, but something about the raised voices I’d heard from the other side of the door unsettled me. I pulled back slightly, glancing at her with a raised brow.
“What was that yelling?” I asked as soon as she opened the door. I peered over her head, unsure of what I’d find.
“Oh, it’s your father.” She waved a hand dismissively, stepping aside to let me in. “Don’t worry about it. We’ll talk later.” She was already pivoting toward the kitchen, gesturing for me to follow. “Come in. I have a snack laid out for us.”
I could tell by her calm demeanor that whatever had caused the shouting was either no big deal or something she’d seen a hundred times before.
My mom had always had this ability to make things seem smaller than they were—an admirable skill, especially given how differently she and my father had been received by each other’s families when they first got together.
She’d grown up in one of those families where power and wealth were inherited, not earned.
Her father had disapproved of my father for years, seeing him as little more than a blue-collar guy from a family that owned a pizza joint in Brooklyn, not someone who belonged in the same circles.
But my mother had persuaded my grandfather anyway, throwing caution to the wind in a way that would’ve been unthinkable for most people of her background.
Eventually, her family had come around, not wanting to lose their only daughter.
“You look good, sweetheart,” she said, steering me toward the kitchen, where she’d set out a plate of olives and prosciutto. If there was one thing Eloise Rossi loved to do, it was host. “How’s everything?”
“Good,” I said, reaching for an olive. My mind kept circling back to the shouting, but I tried to push it aside. “Dad’s alright?”
“Your uncle called.” My mother pursed her lips. “There seems to be an issue with the restaurant. Your father’s your father. He’ll calm down. Don’t worry about it.”
“What do you mean?”
She sighed, collecting another jar of olives from the pantry. “It’s the same old story. The restaurant’s in trouble again.”
I raised an eyebrow as I reached for a slice of cheese. “Trouble? What kind of trouble?”
“Your father’s family hasn’t updated anything since they built the place.
They still run it the way they did back then—no website, no marketing.
Just hoping people will walk in.” She shrugged as she dumped more olives out for me.
“Your father thinks some changes need to be made, but your uncle always sides with your grandparents, doesn’t want to make waves. ”