Price of Admission

Winston enjoyed tending bar at the illustrious Cobalt Cove Oceanside Resort–it allowed him to indulge in what truly fascinated him; the lives and dynamics of its nauseatingly wealthy guests. The bar dutifully served a wide array: senile golf enthusiasts who hate their wives and love their cigars, women in their forties who hate their children and love their Birkins, and freshly graduated “finance bros” who undoubtedly secured their coveted investment banking jobs through blood rather than merit. Winston despised them, but he couldn’t seem to tear his eyes away.

Their conversations evoked a concurrent sense of amusement, resentment, and envy within Winston. “Yo, should we go skiing in St. Moritz or Saas-Fe for New Year’s Eve? We can charter my dad’s plane, it’ll be chill. Your newborn baby? Dude, just leave him with my travel nanny, Amabella. She speaks four languages and she’s super hot.” Winston had conversations like these, too, but only in his dreams. He would never admit it, not even to himself, but he wanted to be a part of these incredibly fanciful conversations. Ski trips, private planes, hot nannies…Winston yearned for it. Winston deserved it. And, despite his crippling student debt and tumultuous home life, Winston decided that he would have it.

“Is Cobalt Cove always this packed on Labor Day weekend?”

The voice was directed at Winston–a rarity. The few guests that made conversation with him were usually lonely cougars seeking more than a nightcap or teenage boys bribing him for booze–both of which Winston briefly considered. To his surprise, the handsome young man speaking to him was none other than Preston Wolcott. Forbes’ “Top 30 Millionaires Under 30” Preston Wolcott.

“You can see me?” Winston murmured to himself, stunned. “Uh–I mean, yeah. Memorial Day weekend’s worse though.”

He glanced at the tech mogul and suppressed a scoff. Salmon-colored polo T-shirt, khaki shorts, flip flops, sparkling Audemars Piguet wristwatch. Straight out of a Vineyard Vines ad.

“Sucks to be you right now. Gimme another gin and tonic,” Preston downed the remains of his highball and slid it over. No please, no thank you. “How much does your job even pay? It’s, like, hourly, right?”

Winston pretended to think for a moment. “Uh, like, seventeen-something an hour. I usually have decent luck with tips, though,” he mumbled sheepishly. With a white-knuckled grip, Winston poured him another drink.

“Damn. It really does suck to be you,” Preston chuckled. He reached into the back pocket of his khakis and slapped down three crisp one hundred dollar bills. “All yours, homie.”

“Whoa, n-no! That’s way too much, man. I couldn’t.” But he could. And he would. But Winston knew this dance, knew it was the politically correct thing to say after being given a generous gift. Rich people ate that shit up.

“Nah, seriously. Keep it.” Preston ran a hand through his bronze locks and lifted a vape to his lips. Winston opened his mouth to remind him of the resort’s no-vaping-indoors policy but refrained. Instead, he gave Preston a garnished drink and a heartfelt thank you.

“‘Last bartender was on my case for vaping here. Thanks for being chill about it, man. What’s your name?”

Millionaire tech mogul wanted to know underemployed bartender’s name? Winston momentarily forgot his own name before coughing it out.

“I’ll call you ‘Winnie’,” Preston flashed a dazzling grin at him before blowing O-shaped rings of cherry-scented vapor in his face. “I’m having a little shindig in my suite tomorrow night. Last weekend of summer, we gotta make it count. Suite seven twenty-two.”

Winston opened and closed his mouth like a fish out of water. Was this a joke? “I’m… working,” he finally managed.

“No worries, we like to stay up late.” Preston chugged the remains of his drink and hopped out of his stool before giving Winston a chance to respond. “Be there,” he called over his shoulder.

Later that night, Winston stood in the kitchen of his studio apartment and stirred his bowl of instant noodles with more intensity than required. He couldn’t get the other young man’s words out of his head. Hefty tip aside, who was he to speak down on Winston in such a demeaning way? Such gall Preston had to insult his job and assign him a nickname better suited for a Shih Tzu!

What enraged Winston most was, despite the dehumanizing encounter, he felt an inexplicable sense of delight and intrigue. He was pleased that the Playboy millionaire had deemed him “chill” enough to attend one of his parties. What was wrong with Winston? Where was his self-respect?

No, Winston decided. He would not be in attendance. He would catch Preston in the lobby tomorrow and nonchalantly tell him, “Thanks, but no thanks. I already have plans for tonight.” And he wouldn’t be lying; every weekend, after his shift at the bar, Winston would make DoorDash deliveries until two in the morning before retiring to his apartment to indulge in cheap boxed wine.

A pounding on Winston’s apartment door stopped him in his tracks. The oven clock displayed “3:30 AM” in neon green. He instantly leapt for the light switch and peered through the peephole despite already knowing who it was.

“Ignore my calls all you want, Winston, we live in same building! Open up. I know you’re awake, I just heard you using microwave!” Thud. Thud. Thud. The potbellied Greek man behind the door added force to his knocking.

“Markos, you’ll get it! I’ll have last month’s and this month’s rent to you by Friday! I swear!”

“You’ve been saying this for past three Fridays! Enough! I want money by Monday or you are out. Evicted!” Winston’s blood ran cold. His landlord was many things, but he was not a man who bluffed. After a final bang on the door, Markos retreated.

Winston slid to the floor with his back against the door, his head suddenly pounding. His Subaru was already on the verge of being repossessed, and now the roof over his head was as well. What now? Back to his parents’ house in rural West Virginia? He was assaulted by visions of his old job at the Dairy Queen drive-through, his town’s decrepit barns and unpaved roads, and its only two dive bars within a seventy-five mile radius. He grinded his palms into his face.

No! Absolutely not. With a clenched jaw, Winston hoisted himself off the ground and chugged his glass of wine. He had moved to this city to put his art history degree to use, to make a name for himself, to return to that barren wasteland as a champion and rescue his family! Returning home in defeat would not be an option.

Suddenly, a voice rang in Winston’s mind. Loud, clear, and douchey. Sucks to be you, Winnie. Suite seven twenty-two. Be there. He thought of the generous tip Preston had given him. The sparkling watch on his wrist that demanded to be ogled at. The smug grin he wore in his Forbes magazine headshot. The snide comments that rolled off his tongue so easily. It was then when Winston knew what to do.

The following night, Winston stripped his all-black bartending attire and changed into a pair of khaki shorts, a polo T-shirt, and Birkenstock sandals—the closest he could come to emulating the outfit Preston had on the other day. His palms refused to stay dry and he had re-styled his hair a dozen times. The four glasses of wine he had behind the bar were doing little to ease his apprehension.

With a sweaty forefinger, Winston pushed the elevator button engraved with a 7. He had never been in any of the resorts’ rooms, let alone one of its presidential suites. Fear and excitement warred within the bartender’s stomach. The elevator doors opened and Winston followed the faint trace of marijuana and muffled house music towards the door of suite seven twenty-two. He knocked. No answer. He pressed his ear against the door. The weightless laughter of women, the clack of heels on tile, the pop of a champagne cork.

With his ear still pressed to it, the door suddenly gave way. Before he knew it, Winston was face-down on the floor of the suite. Whatever conversations were taking place had ceased. Silence for a moment. Then the room erupted in laughter. Boisterous laughter.

Winston’s ears burned as he helped himself to his feet.

“Can we, uh, help you?” Seated on the floor surrounding a coffee table were a dozen swimsuit-clad twenty-something year olds with quizzical expressions and white residue on their faces. Faint white lines and a rolled up hundred dollar bill sat patiently on the table. The question came from a stunning, yet cold looking Asian girl with a sharp bob haircut.

“P-Preston. He told me to come,” he stuttered, fixing his collar and smoothing his wrinkled shirt.

The girl frowned and cocked her head. “Wait, you’re the bartender! Where’s your bar cart? I absolutely need an espresso martini right about now!” The others seated around her murmured in agreement.

“Can you do an Old Fashioned with extra Luxardo cherries?”

“Make that two!”

“Do you have any sugar-free seltzers?”

Winston hopelessly looked around the suite for Preston. “I’m not the bartender! I mean, I am. But not now. Not here. Like, I’m not working right now,” he stammered. The young group of elites blinked at him.

“Then… what are you doing here?”

“Play nice, Astrid,” Preston appeared in the doorway of his rooftop balcony. In true Playboy fashion, he wore a silk robe that was open to reveal nothing under but a pair of silk boxers, cigar hanging out of his mouth. “The help should be allowed to have some fun, too, you know.”

The millionaire staggered over to Winston and ruffled his hair like the pair had known each other for years. “Everyone, this is Wyatt.”

“I’m Winston.”

“Winston! Winnie! I knew that,” Preston’s words were sloppy and his breath reeked of gin and tobacco. The guests had already lost interest in Winston; the girls began taking faux-candid photos of each other on the rooftop and the boys snorted the last of the party favors on the table.

“I swear, they’re not always this rude,” Preston chuckled, as if he didn’t just refer to the bartender as “the help”.

Winston pretended to not be offended. “All good. But, hey, can we talk? Somewhere private?”

Preston glanced at him curiously, then shrugged. “Follow me. Need more blow anyway.”

Winston followed him down a long corridor to a pair of large French doors. Preston pushed the doors aside to reveal a sprawling bedroom with floor-to-ceiling windows that displayed a moonlit ocean just a few palm trees away. Its beauty was marred by Preston’s dirty socks strewn on the floor, his dirty bong sitting on the nightstand next to the California King-sized bed, his glimmering jewelry carelessly tossed in every direction.

“So, what’s up? What’d you need?” Preston asked from the bed. He dumped the contents of a plastic baggie onto his nightstand and began arranging the contents into neat white lines.

Winston hadn’t thought this far ahead. He knew what he needed, he just didn’t have the words to ask for it. Or perhaps had too much pride. Markos’ heavy knocks and threat of eviction echoed in his mind. Winston clenched his fists so hard that his nails dug crescents into his palms. What did he have to lose?

“Look, man, I know we just met, but I’m going through a really shitty time. Like, beyond shitty. And I know that’s totally not your problem. Like, at all—”

“Have you tried hot yoga? Dude, I swear it’s a total gamechanger,” Preston interrupted.

Winston blinked at him. “Well, my problems are bit more… financial, than spiritual,” he said.

Preston raised his eyebrows.

“I swear I’d never ask in any other circumstances… but my landlord’s on my case… he’s gonna kick me out soon if I don’t have rent—”

“I don’t do charity, bro,” Preston cut him off again. The room was quiet aside from Preston fighting back nasal drip.

“N-no! Not charity. It’d be a loan! I swear, you would get the money back. My rent is probably pocket change for you, anyway,” Winston felt sweat bead down his forehead.

Preston snorted. “Pocket change or not, the Wolcotts don’t do monetary favors. My dad told me it’s a slippery slope and shit always gets messy. Best not to partake.” He does another line.

“But, here. The rest is all yours, man,” Preston tossed him the rolled up hundred. “Enjoy,” he called over his shoulder as he exited the bedroom.

Winston stood there, deflated and defeated. If possible, his body grew hotter with humiliation and anger and hopelessness. He had degraded himself to the point where he was begging for money for a roof over his head. How did he get here? Tears threatened to spill but Winston refused to let them fall.

A glimmer in the corner of the room caught Winston’s eye. He looked closer. Tossed carelessly on the ground was an emerald green Rolex. Three gold Cartier bangles sat on the kitchenette counter. Another fancy wristwatch that he couldn’t identify laid haphazardly on the bathroom sink counter.

Winston’s mouth grew dry. Again, he knew what he must do.

Moments later, Winston peered down the corridor for the suite’s inhabitants. More than half of them were filing out to the balcony, champagne glasses in hand, ready for the Labor Day fireworks show.

With heavy, clinking pockets, Winston scurried down the hall, out of the suite, and into the elevator. As the elevator descended, his heartbeat skyrocketed. He let out a maniacal chuckle and gripped the salvation in his pockets with sweaty hands. A weight that had been crushing down on him for years became a lot lighter. Not gone, but lighter.

Months later, Winston’s life had taken a new shape. Just one of Preston’s watches had awarded him three hundred grand. He hadn’t even pawned off the other pieces of jewelry yet—he didn’t need to. The roof over his head wasn’t going anywhere. He paid off his Subaru in full. Winston kept his bartending job at Cobalt Cove, and allowed himself to indulge in past temptations. He took bribes for booze from teenage boys. He let married women—sometimes men—take him home from the bar; in exchange for a fee.

Winston’s head was not simply above water, but he had made it to land completely. He could breathe. Pride and shame were things of the past, and life was better because of it. This was his price of admission.