Winner Takes All
Chapter One Eleanor
Most musicians I know have a preshow ritual. They drink tea with honey, or they huddle up with their band and say a prayer. Or, in the case of one particularly eccentric indie artist I signed a while back, they scramble an egg on a hot plate backstage and hand-feed it to their bichon frise, Ringo.
For nights like this, I have a ritual of my own.
One that involves getting my hair blown out, a single glass of white wine at the hotel bar, and the Louboutin stilettos I splurged on after I negotiated my first major contract at the label.
The shoes make me want to saw off my own toes, but they also make my legs look incredible and are therefore perfect for meetings that have me feeling like I’m the one about to step onstage.
I have to sign this band.
Not just because I genuinely love their music and know I can help take them to the next level, but because I am desperate for a win.
And Dempsey is a sure bet. They already have a solid fan base, have proven they can bring money in.
Word has spread that they’re unhappy with their current label.
If I can close them, it will make up for every underperforming EP and personal failure of the past year.
I drain the last sip of my wine and put a tip down on the bar, then make my way outside to where my Uber driver is waiting.
As he pulls away from my hotel and onto the Strip, I pop my earbuds in.
Ninety percent of the time I’m listening to new music, demos my reps send me or unmastered tracks from an artist already on my roster.
But right now I find my favorite playlist, full of familiar songs that demand I think only about what I was doing, what I was feeling, the first time I heard them.
Songs that drive out every other thought in my head within a few beats.
Which is what I need—a distraction. No irritating little voice reminding me I already had a chance to sign this band five years ago and failed.
Barely three songs later, we’re pulling up to the posh steak house where I’m having dinner with Dempsey.
“Thank you,” I say as I reach for the door.
“Have a good night, ma’am.”
Ma’am. I pause and glance down at my outfit—a black leather pencil skirt and cream silk blouse. Is it giving ma’am energy? That is… less than ideal. It’s too late to go back and change my clothes at this point, so I choose to believe he addresses every woman over the age of twenty that way.
“You too.” One last deep breath, and I’m out of the car, heading toward the ornate double doors. I rub a finger over my front teeth in case of any rogue lipstick and smooth a hand over my hair.
Inside, my heels click against the marble tiles as I approach the hostess stand to give my name.
The entrance is lavishly decorated with metallic wallpaper and gold leaf trim.
Ostentatious, like the rest of Las Vegas.
Before I have a chance to take it all in, I’m being led to a large curved booth along the edge of the dining room.
The two Dempsey siblings and their two bandmates are all seated on the crimson velvet upholstered booth, while their manager sits on one of the matching armchairs tucked in across the table.
“Hey, everyone,” I say when I reach them, and Freddie Dempsey stands up first to give me the handshake/bro-hug combo that never gets any less awkward, no matter how many guys greet me that way.
I work my way down the line, exchanging handshakes and air-kisses with Freddie’s sister Sheridan and the band’s manager, Fiona.
Curtis Kennedy and Ralph Winters—drummer and bassist, respectively—are trapped in the middle of the booth, so I settle for over-the-table handshakes before finally taking a seat in the armchair next to Fiona’s.
A server comes by to take my drink order—another glass of white wine, which I plan to nurse until this dinner is over.
“How does everyone feel about getting some pulpo for the table?” Ralph asks.
“Sounds great,” I tell him. “I love pulpo.”
I have no idea what pulpo is. But I flew to Las Vegas prepared to give these guys whatever they wanted.
Which is why I chose this place, even though this dinner wasn’t entirely sanctioned by my boss.
Wining and dining artists is part of my job, but going over budget is a big part of why I’m on the chopping block.
Josie will be pissed when I turn in my expense report, but as long as I have a signed contract to accompany it, I’ll be fine.
The waitress tells us the food will be right out, and Ralph grins broadly before tipping his head back to take in the massive crystal chandelier dripping like rain from the ceiling above the bar.
He’s practically vibrating with excitement, and it reminds me of the way a toddler would dance in their high chair at dinnertime.
This is why I’ve always been fond of Ralph—no matter how successful his band gets, he’s still basically a goldendoodle, endlessly pleased just to be along for the ride.
And then there’s Freddie, who is manspreading so much I have to keep my legs tightly crossed and my feet tucked under my chair to avoid unintentionally playing footsie with him.
The family resemblance between him and Sher is strong—same jet-black hair and fine features.
Same style when it comes to playing the guitar, even.
Between the two of them, Sher is more talented.
She has a better range and a purer voice, whereas Freddie already has a bit of vocal fry.
She’s a star. But Freddie has the bigger ego.
So I turn to give him my full attention.
“How do you feel, now that the tour is wrapping up?”
“Tired, mostly. I’m so ready to sleep in my own bed again.”
“I believe it.”
“Antsy to get moving on the next thing too.”
Across the table from him, Sheridan sighs loudly. “Some of us would like a break.”
Freddie rolls his eyes. “We all want a break, Sher. But we have ten tracks ready to lay down. We should keep up our momentum, is all I’m saying.”
I’m momentarily distracted by the arrival of my wine and the appetizer—it turns out pulpo is a fancy word for octopus. Fantastic—then, my brain catches up: “Wait, ten new songs?”
“I wouldn’t say they’re ready to lay down, exactly.” This comes from Curtis, who tilts his head as though he’s saying it mostly to Sheridan.
“Uh, yeah. I wouldn’t either.” Sheridan adjusts the front of her lurex jumpsuit—it looks vintage, probably from the ’70s. Her style is so fierce. “They also don’t all belong on the same album.”
Perhaps sensing the rising tension between the siblings, Fiona jumps in: “Which is exactly why we’re looking to land somewhere that offers more creative control.”
I smile, grateful for the opening. “Absolutely. That’s something I can offer. More artistic freedom, and a more relaxed time frame for putting out work. If you finish an EP ahead of schedule, great. But at Blue Sky, we don’t have the expectation that our artists churn out an album every year.”
While this sinks in, I take a bite of pulpo and try to ignore the texture of the literal tentacle in my mouth, the way the suction cups attempt to latch on to my tongue in the process.
I chase it with a generous sip of my wine and begin to wonder if I’ll be able to make this glass last all the way through dinner after all.
“That’s good to hear,” Sheridan says. “We don’t want to lose momentum, like Freddie said. But two albums in three years has been… strenuous.”
From what Fiona hinted at during our last call, it was more than strenuous. I get the sense there’s been a lot of discord among the band members ever since they launched their sophomore album. Touring hasn’t helped, because it never does. Artists always come off tour underfed and sleep-deprived.
The server returns to take our entrée orders, and I wait for her to leave before continuing my pitch:
“I think it’s smart that you don’t want to keep fans waiting too long, but you need to be strategic, and make sure the entire team is happy with where the album is at before we launch.”
Freddie shares a look with the others, before leaning forward to rest his tattooed forearms against the table. “We just want to be sure you mean what you say. That there won’t be drama down the line if one person at the label doesn’t like a song, or a cover concept, or whatever else.”
“That’s understandable.” I match Freddie’s posture, perching my wrists on top of the table. “My priority is to help you put out the best album possible, and I promise to do everything in my power to give you guys back some control—of pace and decision-making.”
“Well, in that case…” Sheridan smirks at the others before continuing: “Now seems like a good time to mention we plan to announce who we’re signing with at the wrap party.”
I blink. Turn to Fiona and blink again. Back when I tried to sign Dempsey the first time, Fiona was still green. Dempsey was the only band she managed at the time, and in meetings she never concealed her emotions. But now we’re all older and more seasoned and her face has become impossible to read.
I know Fiona is in my corner—we kept in touch over the years, and she remembers how hard I fought for Dempsey before.
She did me a solid, tipping me off months ago that Dempsey would be looking to move on once their current deal was up.
But this is the third meeting I’ve had with the band since Fiona reached out, and it’s the first time they’ve indicated a decision date. Which, evidently, is tomorrow night.
“Wow. Well, that’s exciting.” My pulse kicks up a notch, and I work to keep my voice level and calm. “Not that I wasn’t already excited to come to your show.”
Tomorrow marks the final show of their monthslong tour. I anticipated it being a blowout, celebrating not only the end of their tour but the official end of their contract with Sin City Sound. But I can’t say I expected them to finalize their next move so soon.