The Bootlegger

So, it was my first day in which I ever got to “run the room.” I had been slowly working my way up the esteem chart in the eyes of my bosses. They were already a big step up from the last winery I poured at – starting here had meant a complete wardrobe upgrade.

I had never owned so many sets of heels in my life, but it was way worth it. I now work at a place that is highly esteemed, it’s classy time all the time, no nonsense and elegant. True, I miss some of the pranks we used to pull on each other in my old place, but here I’m treated like a pro and there’s a ton of opportunity for moving up.

I had been told a couple of weeks in advance that, on one particular afternoon, there was going to be a closed-door meeting for all the higher-ups – they’d be discussing media relations and seasonal calendar stuff that was still high above my pay grade, but they had chosen me to head the tasting room while they were all going to be occupied.

They wouldn’t be far; in fact, they were going to sip as they conversed in “The VIP Cave.” I think they used ‘cave’ to sound adventurous and mysterious, but it was actually the most elegant rock-lined room of all time. More Marie Kondo than Yogi Bear.

What mattered most to me, however, was that it had one wall that was a full window down into the room where I’d be in charge. If you think that means they were going to be watching me the whole time? You’re right. So, I needed that hour to run as calm and chill as Bob Ross on a lazy river… so it was full on unacceptable that he came in.

My bosses keep the tasting room dimly lit. It’s all candles and intimate corners. One of the things they were going to discuss in the meeting, actually, was what manner of structure to build out front to avoid light bleed into the room whenever the front door was opened. It was the #1 pet peeve to the woman that hired me when a shaft of sun cut across the entire room whenever anyone entered.

Was she a vampire? Perhaps, but she paid well so I’ll take it. Plus, even she had to admit it was usually only momentary as tasters stepped inside. Ten minutes into my shift as the big boss of the room, though, it was opened – and held open, for the longest period of time in the history of open doors.

The heavy door was easily propped open by a suitcase the size of a small refrigerator. The silhouette of my nightmare guest and his bag reminded me of the movie poster for The Exorcist, and guy truly was a demon from my own personal hell.

“So what’s the dealio in a place like this, huh?”

The word “dealio” had never been uttered here. Not ever. That and the prolonged sunlight were the first two things that got me rushing over. He was a squat little guy but his slimy vibe loomed large throughout the room as he stepped in, dragged his sharp cornered suitcase behind him by a leather strap, dragging it like it had wheels (it didn’t). It had sharp metal corners that I swear was going to scrap the room’s imported tile.

“That doesn’t- you don’t- I’m not sure that thing rolls, you know.”

Without thinking, I lifted up the case – which was way heavier than I expected – anything to stop the nails-on-chalkboard effect as he pulled it behind him, banging into every table, stool, and customer knee it could find. Whoever this guy was, I realized, he had annoyingly tricked me into actually carrying his bags for him.

I hoped my boss wasn’t watching. Hell, I wished that nobody was watching, but every eye on the place was giving us vicious side eye while I found him a table in a far corner.

“No need to make me too comfortable. I’m not going to be tasting.”

I lurched to a halt (making the suitcase screech the floor behind me).

“I’m sorry, you’re not? Is there something I can help you with?”

He tipped his boater hat—seriously, what decade was this guy from?—and cracked a smarmy smile that revealed no less than four gold teeth and reached out to shake my hand.

“Help me!?! Oh, dear girl, you misunderstand. I’m here to help you!”

He was taken aback at first when I didn’t shake back, then he looked down to see that I was still needing both hands to carry his luggage. (Though without the suitcase, truthfully, I would have been a tentative handshake at best.) He gave an odd little hop and lowered himself to start unbuckling the box,

“Now you can let go of that. Just let me…”

As he pulled the case out of my hands, I heard an unmistakable sound from inside: the clinking of wine bottles. I figured this was a guy who had been on a tear buying at every winery he went.

“No wonder it’s so heavy. Sounds like you’ve been shopping all up and down the valley already.”

“Shopping? No no, my dear. I’m not shopping. I’m selling!”

He dropped the case to the floor and lifted up the lid to reveal a miniature salesmen’s display inside: Humphrey’s Hell-of-a-Chard!

He had fashioned the suitcase just right so that lifting the top pulled a set of five bottles up into view. It was like a pop-up book of the worst disaster that could happen to me right now.

“I’m sorry. Sir. Sir, you have to get out of here-“

Like a mischievous little gremlin, the scurrying salesman was already off! I gaped in horror as I watched him move to one of my nearby tables. He was giving them the gladhand and diving into a sales pitch, “Well isn’t this your lucky day! Here you are – or at least I think you are, why do they keep it so dark in here?”

This elicited a spatter of laughter and I knew I needed to head this guy off at the pass, “I’ll ask ‘em if they can turn the lights up in here, I have so many great products to show to you-“

Not at all sorry that I was interrupting him mid-spiel, “Sir, I’m going to have to ask you to leave.” He seemed miffed, “I don’t see why, my presence here is giving your customers double the chance to taste the wonders of the region. Here, let me give you a free bottle in the spirit of mutual entrepreneurship.”

This guy’s hands were quicker than a magician. Before I could protest, I was actually holding one of his bottles and he was whispering to me behind his hand like we were special confidantes, “That bottle costs dozens of dollars, but I know you and I are about to make a fortunes off these thirsty marks, aren’t we?”

For his next trick, the shyster pulled out a sheet of business cards from the suitcase—they weren’t even popped out of the Office Depot templates he had printed them on. There he was, in the middle of my tasting room, passing out his business cards, “I grow all my grapes in house—in my garage to be truthful—but I think you’re going to find the bouquet doesn’t bear even a hint of car exhaust, just trust me on that. I’ll try to fix us up with some glasses.”

I was floored by the nerve of this jerk as he actually turned to me, lifted a glass off a table and gave it a little tap, “Could you grab a few of these for me, honey?”

I sneered, balling my hands into fists, just moments away from punching Willy Loman here so hard it would be Death of a Salesman for sure. Then I noticed movement up in the VIP Cave. Some of the higher-ups had started to take notice to the commotion on their tasting room floor. I swallowed hard and refocused.

No, I couldn’t kill this guy—that, in itself, would have been a bit of a party foul on the floor. What I had to do was get rid of him. Fast. I was worried it was already too late, especially as my sneaky little bootlegger spied my bosses up in the VIP. He could tell at first glance that was where the real money was. Tossing his flimsy “business cards” only each of my tables along the way, he laser focused on the last people in the world I wanted him to talk too.

I ran faster than I thought high heels cold carry me and whipped around in front of him, “Just where do you think you’re going?”

His eyes narrowed, trying to gauge just how many millionaires were behind the glass wall behind me (for the record, three of them).

“So tell me about what’s going on in there, huh? Spill the beans or I’ll start shouting that I see a cockroach in the Sauvignon.”

There was no way I was going to rid my tasting room floor of this creep without sinking to his level.

My confession is that I lied, right there. Feet away from the risk of exposure. I needed him out. Needed my bosses not to be disturbed. So, I made up a desperate story that might just kill all my birds with one lying stone.

“That? Oh. That’s the IRS.”

I swear I saw the gold melt right out of Willy Loman’s teeth.

“I-I-I’m sorry, who did you say?”

Right there, I could tell it was working. So I turned down the urgency and used a big brush to nonchalantly paint some more layers over the lie, “Oh yeah. They work in auditing. Every once in a while they take over that room, drink their fill, and go over some of the records in the area of people who might be taking liberties with their small businesses and such. They seem like good peeps but I’d hate to get on their radar, know what I mean?”

There was a swirl of fear, math, guilt, and regret whirling around just behind his eyes. A guy operating a home distillery in his garage—peddling from a suitcase on other people’s property—there was no way a character like that was on the up-and-up with the taxman.

“Tell you what. You’re right. I’m sure they would absolutely LOVE to hear all about everything you do to make money with Humphrey’s Hell-of-a-Chard!”

I was impressed with the speed that squat little dude could hit when motivated with just enough financial fear. He spun on a hell, folded up his makeshift travelling pop-up store, and skedaddled faster than you could say ‘IRS Audit.’ I was safe.

It turns out that I always was, however. Later that night, after my shift, my boss took me aside, “Hey, I saw you had that guy Humphrey in here.”

My heart thumped in my throat. I wasn’t in trouble, however, just the opposite; “How’d you get rid of him so fast? Last time he was in I had to call the cops?”

I smile and told her my story, “… so, no, I don’t think you’ll have to worry about him again.”

She gave me a wide smile and thanked me. Looks like I had gone above and beyond. I’ve never seen Humphrey again – and, believe me, I would recognize him in an instant. If I did, I doubt I would mention to him what I did that night after he almost ruined my career. He had, after all, left me with a free bottle of his wine.

What, I’m going to not try it? No, I had to know. I got home, took off my heels, put my feet up, and took a sip of Humphrey’s Hell-of-a-Chard! You know what?

I was very surprised. You actually could taste a hint of that car exhaust.

For Kevin, being a writer has always required a great deal of wine. He never dreamed he’d be able to combine his love for the two. His screenwriting includes works for Paramount, MTV, Warner Brothers, 20th Century Fox, Bad Robot, and his role as Executive Story Editor on “Blood & Treasure,” an action adventure show on CBS and Amazon. Before that, his thirst for sketch comedy led to pieces for The Onion and National Lampoon – as well as the stages of UCB, HBO Workspace, Comedy Central Stage and festivals in San Francisco, NYC, Vancouver and beyond. He’s a write-at-home dad always ready for a winery road trip… especially a dog-friendly one.