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UNDERCROWN MADURO BY DREW ESTATE

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You know, sometimes you come across something that’s built on the back of a legend, but it’s still got its own grit. Like a good, solid hunting knife that might not be a custom job, but it’ll hold an edge and get the work done. That’s kind of how I look at this Drew Estate Undercrown Maduro.

Drew Estate, they’re known for those infused sticks, the ones that smell like a dessert cart. But then they dropped the Liga Privada #9, and that thing was a beast – full-flavored, a real treat. The problem with those top-shelf items, though, is they are not always easy to come by, or easy on the wallet. So, what do you do? You get resourceful.

The Undercrown, from what I gather, was born out of that kind of thinking. The folks rolling the Liga Privada in the factory, they put their heads together and figured out how to use similar tobaccos – stuff that’s more readily available – to make something that hits a lot of the same notes, but without the sticker shock. It’s a notch down in strength from the #9, sure, but sometimes, you don’t need to be wrestling a grizzly bear; a good black bear will do just fine.

This particular stick, the Undercrown Maduro, comes out of Nicaragua, a country that knows a thing or two about growing good tobacco. For about $12, you’re getting a solid piece of work. The wrapper is an Otapan Negro Último Corte, which sounds like something you’d find deep in the jungle. The binder is a T52 Connecticut River Valley Stalk Cut & Cured Habano, and the filler is a blend of Brazilian Mata Fina & Nicaraguan Cuban Seed. That’s a serious mix of dirt and sun right there. And the overall composition? Is Good, Really Good.. The strength on this one sits right in the Med-Full range, which means it’s got some backbone but won’t knock you flat.

First Third: Out of the Gate

You light this thing up, and the first few draws give you a solid, familiar feeling. I got a real sense of oak notes, mixed in with some dark coffee and a rich, almost bitter chocolate. But then, something interesting started to peek through – a hint of dark cherry. I was sipping on a classic Coke with this, and I gotta tell ya, it almost gave it this whole cherry coke vibe. It wasn’t overpowering, just a nice little twist, like finding a patch of wild berries on a long walk. It felt natural, not forced.

Second Third: Settling In for the Long Haul

As you get into the middle, that strong dark coffee and chocolate really take center stage. It’s the kind of deep, robust flavor that sticks with you, like a good, strong brew on a cold morning. Every now and then, I’d catch a whisper of leather and it was never the star of the show.

Now, a word of advice here, and it’s a practical one: take your time with this cigar. If you get too eager, drawing too quickly, and it starts to burn hot, it can get a tad bitter. It’s like trying to rush a stalk; you gotta be patient, let things develop, or you’ll spook the whole show. Slow and steady wins the race with this one.

Last Third: Bringing It Home

The final third of this Undercrown stayed true to form. It was still very enjoyable, consistent with the rest of the smoke. It didn’t fall apart on me, didn’t get harsh or unpleasant, which is a real mark of good craftsmanship.

I usually run through at least three of any cigar before I put my thoughts down, just to make sure I’m not getting a fluke. And I can tell you, this Undercrown did not disappoint me in any of those experiences. It’s a very good maduro to keep on hand, a reliable tool in the kit. In fact, I’m genuinely elated to have two more sitting in my humidor right now. It’s the kind of smoke you can count on, and sometimes, that’s all you really need.

OH NO! I HAVE NEVER HAD A CIGAR IN MY LIFE, WHAT DO I DO?

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Alright, don’t panic. Cigars can be confusing, I get it. I started a little over a year ago and now I am a certified cigar sommelier. But… this is my job, you just want to get by with your buddies so you don’t look stupid. It’s all okay, I will get you to the point of comfort so you can actually enjoy this excursion instead of feeling like you have to ace a final.

So, you’ve decided it’s time to grasp the fundamentals of a good cigar. Maybe you’ve got a new golf buddy who savors a smoke on the back nine, or your best friend is getting married and all the groomsmen are sharing a cigar experience. When I started out, I couldn’t tell a foot from an elbow. I had no idea how to light a cigar, that flavor profiles were even a thing, the shapes, sizes, wrappers… what??? It’s a lot of information, I know, but let’s simplify it so you don’t embarrass the crap out of yourself. Trust me, nobody wants to be “that guy” fumbling with a stick when everyone else is enjoying a quiet moment. It’s easy for the world of cigars to feel a bit overwhelming, even expensive, but there’s no need to spend hundreds of dollars right out of the gate. We’re just here to cover some basics. Don’t feel out of your depth; every master of a craft started as an apprentice. I’m here to lay out the groundwork, ensuring your maiden voyage into the world of cigars is marked by confidence, not by fumbling.

The Cigar’s Blueprint: Anatomy of the Stick

Before you even think about putting flame to leaf, understanding how a cigar is put together is paramount. This isn’t some haphazard bundle of dried tobacco; it’s a precisely engineered piece of work, a real testament to skilled hands. Think of it like a well-built tool – each part has a specific job.

  • Foot: This is the end you’ll light, usually open and ready for business.
  • Head: The opposite end, the one that goes in your mouth. It’s almost always capped and needs a clean cut.
  • Cap: A small, carefully applied piece of leaf that seals the head, holding the wrapper tight. Mess this up, and your cigar will unravel faster than a bad fishing knot.
  • Wrapper: The cigar’s outermost layer. Often the prettiest leaf, and usually the most expensive, it plays a big role in the cigar’s main flavor and how it smells. It’s the face of the operation.
  • Binder: Tucked just under the wrapper, this tougher leaf holds the filler tobacco together. It’s crucial for a steady, even burn. This is the unsung hero, keeping the whole thing from falling apart.
  • Filler: The very heart of the cigar, made up of different tobacco leaves – sometimes from all over the globe. These leaves collectively decide the cigar’s strength, its complex taste, and its overall character. This is where the true essence, the real flavor, makes its home.

Selecting Your First Charge: Exercise Prudence

This rule stands firm. Just like you wouldn’t start learning about spirits by chugging a barrel-strength whiskey, don’t jump straight into a full-bodied, heavy cigar. Your palate needs to ease into it. Start sensible, like picking the right caliber for your first hunting rifle.

  • Seek out mild to medium-bodied selections: Good starting points include the Macanudo Cafe, an Arturo Fuente Hemingway Short Story, or an Ashton Classic. These offer a balanced, easygoing smoke, without knocking you flat. You don’t want your first puff to feel like you just swallowed a mouthful of campfire smoke.
  • Consider a ‘Flavored’ Introduction: Some beginners find an easier path in with a quality infused cigar. We’re not talking about those sickly sweet things you find at a gas station, but reputable brands that infuse their tobacco with subtle, often natural, sweetness or other pleasing aromas. These can be a gentle bridge, helping someone new to tobacco find some initial enjoyment before they learn to appreciate the pure, unadulterated flavor of traditional cigars. A solid recommendation here is the Drew Estate Deadwood Series, like the Fat Bottom Betty or Sweet Jane, known for their unique, sweet notes without being overly artificial. Think of them as training wheels for your taste buds. It’s a stepping stone, not the end of the trail.
  • A word of caution: This might be your pre-excursion cigar. Among truly serious cigar users, stick with a straight-up mild-to-medium bodied suggestion like those mentioned earlier. Why, you ask? To save yourself some embarrassment. Seasoned cigar smokers might try to pull your man card or give you a hard time if your cigar smells like a bowl of Fruity Pebbles. To them, those are often seen as toys for kids, not serious smokes for grown folks around the fire.
  • Heed the vitola (size): Smaller cigars, like a Robusto or a Corona, are a smart move. They burn quicker, giving you a good introduction without having to commit to a long smoke that might wear you out. You don’t want to be stuck with something you’re not enjoying for an hour.
  • Consult the purveyor: When you’re in a respectable tobacconist shop or a dedicated cigar lounge, tell them you’re just starting out. Ask for a mild, beginner-friendly cigar, and don’t hesitate to mention if you’re interested in a quality infused option, like something from the Deadwood Series. These folks are like seasoned guides; their knowledge is worth its weight in gold.

The Decisive Cut: Mastering the Blade

You absolutely cannot, under any circumstance, just bite off the end – that’s a rookie’s blunder, a real rookie move. A precise cut is essential for a clean draw and an even burn. Treat your cutter with the respect you’d give a sharp camp knife.

  • Common Cutting Implements:
    • Guillotine (Straight Cut): This is the most common and straightforward tool. It gives you a clean, decisive chop. Simple, effective, no fuss.
    • Punch Cutter: This tool makes a small, round hole in the cap. Some folks prefer it for a slightly tighter draw. Like drilling a small pilot hole.
    • V-Cutter (Cat’s Eye): This one makes a distinct “V”-shaped notch in the cap. For those who like a bit of finesse.
  • The Unbreakable Rule: Always cut above the cap line. Your goal is to just snip enough of the cap to create an open channel for the draw, without messing up the wrapper. A common mistake is cutting too deep. If you go too far, that wrapper will unravel faster than a bad rope in a white-water rapids, and you’ll be left with a sad, floppy mess of tobacco. Aim for one swift, confident action.

Ignition: The Ritual of the Flame

Lighting a cigar is a distinct skill, not like haphazardly flicking a lighter for a cigarette. It’s a deliberate act to make sure you get a broad, even light. Take your time with this, like you’re building a good fire in a chilly camp.

  • Preferred Fire Starters:
    • Butane Torch Lighter: This is the top choice. It throws a clean, odorless flame, free from any gunk. It’s your dependable workhorse.
    • Wooden Matches (unwaxed): An old-school method, a bit more challenging. Let the sulfur burn off completely before you even think about putting flame to tobacco. It works, if you’ve got the patience of a trapper.
    • Cedar Spills: These are thin, long strips of cedar. They burn slow and steady, giving off a subtle, pleasant aroma. For the purists, or if you’re feeling a bit fancy.
  • The Process:
    1. Toast the Foot: Hold the cigar’s foot just above the flame (never directly in it) and slowly rotate it until the entire surface gets a nice, even char and starts to glow. You’re not setting it ablaze, you’re preparing it, like searing a good piece of meat.
    2. Apply Flame While Drawing: Once it’s properly toasted, bring the flame to the foot and start taking gentle, measured draws, keeping that cigar rotating. Don’t take aggressive, rapid puffs; methodical patience gets you the best results. Think gentle sips, not trying to suck the smoke out with a vacuum cleaner.
    3. Verify the Burn: Check out the cigar’s foot. You’re looking for a consistent, glowing cherry all the way around. If a spot isn’t lit, gently put the flame back to that area. We’re going for an even burn here, not a lopsided hot dog on a stick.

The Smoke: Savoring the Journey

  • Never Inhale: This is the golden rule, and I can’t stress it enough. Cigar smoke is meant to be savored on your palate, not pulled into your lungs. Unless you want to cough like a wild goose caught in a thunderstorm, keep that smoke out of your lungs. Draw the smoke into your mouth, let its flavors linger, and then slowly exhale it.
  • Puff with Purpose: Treat this experience like you’re enjoying a slow-cooked meal after a long day in the field. Avoid puffing constantly. The sweet spot is usually one or two deliberate puffs every 30-60 seconds. Puffing too fast will inevitably overheat the cigar, making it taste harsh and bitter. Don’t puff like a steam engine; you’ll scorch the tobacco and ruin the flavor quicker than a bear raiding a picnic basket.
  • Discern the Evolution: Cigars naturally change in flavor as they burn down. Pay attention to the subtle notes that emerge – maybe you’ll pick up on cedar, strong coffee, a hint of nuts, or a developing spice. It’s a journey of taste, not a sprint to the finish line.
  • Respect the Ash: Don’t knock the ash off too soon. A longer ash actually helps insulate the cigar, keeping its temperature steady and promoting a cooler, more even burn. Let it build up to a good length, perhaps an inch or more, before gently rolling it into an ashtray. Think of that ash as a temporary trophy; let it grow, then let it go.
  • Knowing When to Conclude: When the cigar starts getting uncomfortably warm to the touch, or its flavor turns harsh, or simply when you stop enjoying it, that’s your cue to set it down. There’s no law saying you have to smoke it down to the very nub. Don’t be a hero; when it stops being good, it stops.

A Word on Decorum and Preservation

  • Ash with Responsibility: Always use a proper ashtray. Don’t be a slob; nobody likes rogue ash on the patio.
  • Relighting Protocol: While you can relight a cigar if it goes out, try to avoid doing so after a long stretch of time. The flavors trapped inside will be ruined. If it’s been sitting cold for ten minutes or more, it’s likely done for.
  • The Humidor: If you plan on buying more than just a handful of cigars, investing in a proper humidor is essential for keeping them fresh over the long haul. But for getting started, your tobacconist should give you a good bag for transport. Ask them if you can also pick up a Boveda pack for a small fee. This little, vital packet will keep the humidity just right, giving your cigars months of protection while you figure out if this pursuit is truly for you. It’s an inexpensive bridge, letting you test the waters before you sink a chunk of cash into a dedicated humidor. For now, let’s just get you squared away.

Embarking on your cigar journey is a commendable step into a world of deliberate relaxation, refined tastes, and good company. With these fundamental principles locked down, you’re now ready to approach your first cigar with unwavering confidence and, indeed, genuine satisfaction.

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