In each season of The Harem, there is inevitably at least one entry where I smoke a novelty-sized cigar and suffer through a final two hours where afternoon has turned to evening and smoking weather has turned to shit. The Hoyo de Monterrey humidor of 2004 was a series of 500 bland looking boxes in light wood, that would match nicely with your Ikea cabinetry. They were exclusive to La Casa del Habano stores, and any other retailers that cared to order them. The boxes contained 100 cigars, 50 pieces each of a Gran Pirámides and a Diademas. The Pirámides is notable for being an early example of the 57 ring; the Diademas has some history. Named the Monterrey, it is a return of a grand old cigar that was discontinued in the 1980s. Unfortunately, these aren’t wrapped in foil like the old ones were.

I have long contended that the Diademas vitola is not really for smoking. They’re there to admire. Show your friends. Pose for a photo with one clenched between your teeth. Take a moment to appreciate the skill it takes to roll something like that. But leave it at that. Nobody really needs to spend four hours smoking the one cigar.

Like all Diademas, when I light the Monterrey it begins very smooth, the cool smoke well filtered by nine inches of leaf betwixt coal and lip. There is the slightest cinnamon note, and a grain or two of sugar. Somewhere in there is a hint of tobacco, of coffee, and the lactic edge of cream. In order to make these cigars bearable, they need to roll the foot with the lightest leaves they can find as all the tar from the journey will build up in the head. If they were to use a stronger leaf at the foot, the final few inches would be unbearable.

I was thirty-three years old in the year I attended Ted’s twenty-second birthday party. Ted (born Téodor) was a friend from work; my opposite number in a business that shared our offices. We were similar personality types, both nerds with a taste for degeneracy, and had bonded over coding computers and getting lit. At work, our age difference wasn’t normally a factor. We were colleagues, and related as such. At the party though, it was being thrown into stark relief. The room was full of people ten and fifteen years my junior. The music was loud and unfamiliar. Drug use was abundant, and the way the reckless youth were making a mess of somebody’s parents’ house was causing a lot of tension in my homeowner’s stomach. People were leaving marks that weren’t going to come out. I hadn’t seen even one coaster.

My case of impostor syndrome was terminal, and I found a couch in the darkest, quietest corner with the only other middle-aged man in the place. We were discussing the merits of variable vs fixed-term interest rates when Beatrice presented herself before us.

She was five-foot-ten wearing a four-inch skirt and a singlet top. The couch we were on was badly collapsed, and slumped in it, we were at eye-level with her kneecaps. Strawberry blonde, with a button nose and bee-stung lips, I would later learn that she was a model. At that moment she was only a humiliating manifestation of our departed youth.

“Get up.” She said, “I can fix those cushions for you.”

We hauled ourselves from the pit, and watched as she scrabbled about on all fours, vigorously plumping the cushions and adjusting the covers until the couch stood firm and erect.

“Jesus Christ” I muttered under my breath as she flounced back into the crowd. “So that’s how they’re making them these days.”
“You know who that is?” my sofa-mate replied. “That’s Beatrice. That’s Ted’s kid sister. Nineteen years old.”

Six months later, the workplace that Ted and I shared organised a trade mission to Silicon Valley. Five days. Ten tech entrepreneurs, along with a couple of dozen public servants and academics would be touring campuses, attending talks, eating free lunches, and networking with whatever Valley barnacles they could scrape up for something like this. A proper junket.

I checked into the hotel and, already in full junket mode, headed down to the lobby bar to get a head start on the cocktail meet-and-greet. There, playing with her phone next to a pile of Autumnal gourds (it was November), was Beatrice.

I sipped my beer in a nearby lounge chair and contemplated her a while. She glanced at me a few times, but if she recognised me she gave no indication. Eventually her brother materialised.
     “Hey man, how’s it going? Have you met my sister before? She’s going to stay with me for a couple of days. Free hotel, right?”

As the Monterrey crests its widest point, it becomes a little bitter for a moment, with full notes of roasted coffee. The upsurge soon passes, and the cigar slips back into the mild range. The coffee note is still present, now more cappuccino than espresso, with cream and vanilla bean joining it. The day is sunlit and lazy, and ninety minutes in, the novelty cigar is turning out to be really very enjoyable.

Ted was by far the youngest of the entrepreneur contingent, with the others ranging from late twenties to early forties. The academics and journalists were in their fifties and sixties. It was the standard demographics of a tech convention. Ninety percent men. One-hundred percent nerds.

Beatrice mostly sat out the lectures and the campus tours, but she joined us for our nightly bar-crawls, and was the source of many raised eyebrows. She had a fake ID, liked to drink, liked to smoke, and wasn’t afraid of shots. She also wasn’t shy about arguing, and didn’t have a lot of respect for the corporate hierarchy. For her nineteen years, she’d lived a life, and had some very bawdy stories to share.

When she and Ted weren’t present, the gossip often turned to Beatrice. One night a few of us were having a nightcap back in the room, when someone pulled out a phone. “Check this out guys. Have you seen her Instagram?”

It was what you’d expect from a 19-year-old model. Pages and pages of cheesecake shots in lingerie, sheer tops and glamour nudes. A lot of pictures of her butt. “Huh,” Luuk, a dutchman, observed. “She has a nipple piercing.”

When it comes down to it, Palo Alto is a very small town. The downtown strip has only four bars, and three of them close at eleven. Every night of the junket saw us propping up the bar in one that says open late, and every night we would have a run-in there with one or other character of the valley: senior executives from Samsung Korea, drunk and very merry; Stanford AI researches who’d just got a big grant; and briefly Ariel Zuckerberg, who looks exactly like her brother. It wasn’t until the forth night though that we had our most memorable encounter.

It was about 9:30pm. Luuk, Geoff and I were in a western saloon themed bar. Ted and Beatrice had been out front having a smoke, and returned, full of laughter. Some guy and his girlfriend, they told us, had been getting into a BMW i8 outside the bar. “Nice car,” Ted had remarked. “Nice girlfriend.” The guy had retorted. “She’s my sister,” Ted had yelled as the guy peeled out. He’d found the exchange highly amusing. Beatrice substantially less so.

Twenty minutes later the guy, having dropped his date off, walked into the bar and seated himself at our table. He was built like a thug, bald and heavyset. His name was Nathan. He was as big an arsehole as has ever been found on this earth. “Sorry about that guys” he said to Ted and Beatrice, by way of an introduction. “I should have noticed you looked pretty similar. I was on a Tinder date with some stuck-up boring bitch. I thought she was a hippy chick, that’s why I brought the electric i8, but she was just some dumb gold digger. I should have brought my McLaren.” Three minutes later he told us he was employee number 41 at Google. “Yeah, y’know, it’s sad,” he reflected. “Google really changed after the IPO… all us early guys got over a hundred million, and people changed.” He flashed his AMEX black card about minute ten. “Yeah, this is the plastic one… y’know, they give you a metal one as well with it, but it doesn’t fit in the machines, you just use it to impress waitresses.” At minute fifteen he showed us the pictures of him as an MMA fighter. “Yeah, I had a few fights. Dana said I could have gone all the way in the UFC, but you never know with that shit. One bad hit and you’ve got brain damage. Venture capital is just more fun.”

In the start-up jungle the apex predator is the venture capitalist. VCs can make companies, and they can break companies, and so each of us kowtowed to this arsehole unremittingly. One by one, he had us give our pitches, the little spiels about our businesses. One by one we were rewarded by the ceremonial presentation of his business card. My own subjugation came when I asked about his car and he took me out to have a look. For a couple of minutes we were just two guys admiring some exotic iron. He opened the scissor doors and had me sit in the driver’s seat. Gave me the spiel about how it was the pre-production version, and how that meant it was better than the one most people had. As we walked back into the bar he announced loudly “Alex just blew me in the car. Dude could suck-start a lawnmower.” I smiled weakly and said nothing.

Most of all, he was boorish to the women. He complimented the waitress on her arse repeatedly. She smiled along, with a deer in the headlights look. They work for tips in America. He told Beatrice she was hot at least a hundred times, interrupting every anecdote she told with lines like “because you’re so fucking hot”. When she turned down a drink saying “I’m fine,” his response was instant. “Oh, I know you’re fine. But would you like a drink?”

When Nathan went to the bathroom the table was split. Luuk, Ted and Beatrice were livid. “This guy is the biggest arsehole I’ve ever met in my life” Beatrice hissed. “If he says one more thing to me I’m going to throw my drink in his face.” Geoff was pragmatic. “It’s just how this town works” he said. “This guy can open a lot of doors for us. You just need to put up with it.” For my own part, I was entertained. “Yeah, this guy is a huge dick” I said, “but don’t you want to see where it goes?”

The others left, and Geoff and I remained. Nathan was disappointed, but was up for the late-night bar. It was around 200m away, but he insisted on driving, somehow managing to break the speed limit in a block and a half. He parked illegally right outside the door. Bouncers in America ask for ID from people obviously decades older than legal drinking age, and sure enough they stopped us on entry. He thumbed at the car. “That’s my ID.” They let us in.

In the bar we did a couple of Fernet shots, and Nathan buttonholed me. “Man, that chick was so fuckin hot. You know her well?”
    “Beatrice? Ah, well, she’s Ted’s sister, she’s a model, she’s a student, she’s nineteen.”
    “Ah, so that’s why! Nineteen! Too young to be impressed by money. Give her a couple of years, she’ll come around. You got any pictures?”

I laughed. “You should see her fuckin Instagram though.” I fumbled with my phone for a few minutes, but couldn’t get it up.

“That’s fine” he said. “You send me it tomorrow.”

The next day, ever the networker, I sent him an email.

G’day Nathan,

Great meeting you last night – let me know if you ever get down Australia way and we’ll do it again.

In the meantime, my business partner will be in Palo Alto in a couple of months and I’d love to hook you guys up.

The response made it clear that this was a transactional matter.

Nice meeting you to, bro. Sounds good. Don’t forget to send those pictures of that girl.

It was a clear moral test. Here I was, a humble bonobo, with a chance to curry the favour of an apex predator. And yet, for all her bluster, Beatrice was a sweet young girl; she didn’t need me to invite some Silicon Valley creep into her life. In the end I took the high road. My follow up email politely ignored his picture request. There was no reply.

And later I heard that he found her Insta anyway and sent her a bunch of creepy messages, so I guess it all boils out in the wash.

The final third, thickened with the bitumen of a double corona’s worth of tobacco, is punchy and bitter. Coffee and chocolate. 95% cocoa. Some salt. Somehow, it manages to avoid the acrid tar taste, and I take it right the way to the nub.

Perhaps the most notable thing throughout this entire experience has been the absence of cedar, usually the predominant trait of Hoyo de Monterrey, along with a general blandness. Perhaps the Diademas vitola, whose very nature dictates a mild beginning and a punchy end, and forces a bit of character into even the most milquetoast of cigars, suits the HdM profile well.

An excellent cigar, nonetheless. Well worth the time. And much better than an Epicure No. 1.

Hoyo de Monterrey Monterrey Hoyo de Monterrey Humidor 2004 on the Cuban Cigar Website.