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Joshua Stephens | Nov 18, 2025

The Slowburn: The Best Worst Cigar I Ever Had

Many years ago, I spent a week under the Mexican sun at Haven Riviera Cancun with friends and family…the kind of trip where everyone’s vibing, everyone’s sipping, and everyone’s on island time…except the lone cigar guy in the group.


Ya boy.


Relegated to the smokers’ area like a feral cat wandering the resort grounds looking for a patch of shade and a moment of peace.


Mexico used to be a cigar paradise, back when cigar lounges were tucked inside every resort like little sanctuaries for the leaf. Dark wood, leather chairs, humidors humming like a choir. But over the last few years, the country tightened its smoking laws with the type of precision only government bureaucrats and angry HOA board members possess.


As a sober smoker, the crackdown hits different.


While everyone else is throwing back Scooby snacks and pounding mini-beers like they’re being timed, I’m over here trying to find a quiet spot to light up and lean in.

Not easy when the government decides smoking is basically sorcery.


In 2023, Mexico rolled out what might be the strictest tobacco laws on earth, no smoking in public. No beaches. No hotel patios. No nothing. Add a total ban on advertising, promotion, or sponsorship, and suddenly those once-romantic cigar lounges get repurposed into juice bars or yoga studios where Chad and Brittany can realign their chakras.


But the trip I’m talking about happened before the purge, back when you could still catch a faint waft of something glorious drifting across a pool deck.


So… back to the beach.


Traveling with a group always turns into a weird sociological experiment.

Everyone’s got their own ideas of paradise:


someone wants adventure


someone wants to shop


someone wants to sit in a chair for seven hours


someone inevitably tries to schedule a group activity at 7:00am


Eventually, we agreed on one shared quest:


Take a catamaran to Isla Mujeres.


We rented golf carts, zipping around the island like a broke version of Mario Kart, and eventually headed toward Tortugranja, a sea turtle sanctuary we’d read about. Educational. Wholesome. Instagrammable. A great story for later.


Except…


It was not what I thought it was.


What we walked into wasn’t a sanctuary.

It was turtle jail.

Different Yards. Different levels of security.

A full-on reptilian penitentiary dressed up as an “animal experience.”


"Clink."


That was the sound, the unmistakable prison-door clank, that echoed behind us as we stepped into Tortugranja. Not the soothing, ocean-sanctuary vibes I had pictured in my head. Nah. This wasn’t “Finding Nemo.” This was Shawshank Redemption.


Instead of a peaceful conservation refuge, it felt like we walked into Turtle County Jail, complete with different Yards.


1 Yard?


That was minimum security. The turtles there looked like white-collar criminals…accountants who fudged a few too many tax documents. They were pacing slowly, staring out into the distance like:

"If I ever get outta here, I’m goin’ straight."


2 Yard?

That was mid-security; the turtles who might have gotten into a bar fight or sold some questionable seaweed. They gave us that slow, squinty side-eye…like they were sizing us up:

"Yeah, you ain’t from around here, are ya, turista?"


And then…


3 Yard.

Maximum security.

Where the hard cases were. The repeat offenders. The turtles who’d seen some things. Their shells were cracked like they’d been through a few prison riots. These dudes were posted up in the corners like:

"What you lookin’ at, bro? You want the smoke? Didn’t think so."


There was one big-boy turtle, had to be like eighty years old, just staring at a patch of algae on the wall like Red from Shawshank. I swear if he could talk, he would've said,

"Been here since ’74… ain’t leavin’ till they fix the filtration system."


Meanwhile, the juvenile turtles were in another little holding cell, a daycare/solitary confinement combo, splashing around like they were plotting the next great escape.

One tiny turtle kept ramming the side of the tank with the kind of energy that said,

"I may be 4 inches long, but I WILL taste freedom."


I looked around and thought:

This is what happens when Pixar lies to us.


These turtles aren’t out here riding East Australian Currents hanging loose with Crush.


They're serving time.


Hard time.


If there had been a commissary window where you could buy shrimp with turtle stamps, I would not have been surprised.


Our time at Turtle Jail eventually came to an end, and we headed back downtown to do some shopping. You know how it goes…split up, wander, let the sights and sounds tell you what you “need” even though you don’t actually need a thing.


But me?


I did what any brother of the leaf does in a foreign land:

I went hunting for fellowship.


Near the docks, I found a little shop selling all kinds of alleged “Cubans.”

You could practically smell the counterfeits from the doorway.


But I still walked in, like a hopeful romantic.

I gave the boxes a once-over, the way only seasoned smokers do:


Factory codes?


Date codes?


Does the Garantia seal have the QR hologram or does it look like someone printed it off an old Dell inkjet?


Are the bands embossed or flat like kindergarten craft paper?


Are the colors slightly off, like a bootleg DVD cover from 2009?


After bartering over a box of “Siglo IVs,” I walked away.

Seal broken.

Vibes off.

Desperate sales pitch.

Everything inside me screamed, “These ain’t it, brother.”


As we made our way back toward the boat, my wife offered sweet condolences over the missed Cuban opportunity. Before I could respond, my friend, who I didn’t realize had been shadowing me like a cheerful golden retriever, chimed in: “Bro, don’t even trip. I got you!”


He reaches into his bag and proudly whips out a humidified 5-pack of Cohibas.

“I got these for $30, bro! Absolute steal!”


Someone definitely got robbed…


Still, he was so proud. So genuinely excited to bless me with what he thought was a treasure that I didn’t have the heart to tell him he’d purchased the cigar equivalent of a knockoff Gucci belt in Times Square.


“Let’s smoke these when we get back to the beach,” he said.


Brother…that sounds like a plan.


A few hours later, the sun is dropping behind the shoreline, the breeze is perfect, and he hands me a cigar with the kind of grin that tells you his heart is 100% in the right place.


Within moments, moments, my cigar explodes Yosemite Sam style, unraveling like a cheap party streamer. But I’m committed. I’m trying to cherish his excitement even as this thing tries to fall apart in my lap.


Then I glance over… and he’s staring at his, examining the large canoe forming like he’s witnessing a crime scene. He looks up at me with the most deadpan expression I’ve ever seen him pull off.


“These aren’t real Cubans, are they?”


We both LOST IT.


I’m talking full-on belly laughter…the kind where your lungs tap out and your eyes leak and strangers start checking on you. Two grown men, dying laughing on a beach in Mexico, smoking absolute dog-turds and loving every second of it.


And honestly?


It was the best worst cigar I ever had.


I used to spend so much time with him.


Before sobriety reshaped my life.

Before fatherhood reshaped his.

Before the heaviness crept in and made joy feel suspicious to him.


We’re different now.

Older. Busier.

Weathered by life.


He carries battles he’s not ready to say out loud. Depression and addiction lie; they tell you everyone is against you when, in truth, the people who love you are cheering the loudest.


But when I think of him, I rarely think of the hard stuff.


I think of us on that beach.


Two dudes, sunburned, sand-covered, laughing like kids….smoking terrible fake cigars and not caring one bit.


Just living.

Just being.

Just together.


It didn’t matter that the cigars sucked.

It mattered that the moment didn’t.


And here’s the thing we don’t talk about enough:


You never know when you’re living a “last” moment with someone.


The last time they’re light and free.

The last time they laugh that hard.

The last time life hasn’t yet buried them under a weight they don’t know how to carry.


Sometimes the worst cigars make the best memories.


Sometimes the cheap counterfeits mark the richest moments.


And sometimes the last thing you want to savor becomes the thing you wish you could go back to…one more time.


So when the moment comes…linger.

Laugh.

Lean in.

Savor the slow burn.


Because you might not realize the ember is fading until the ash hits the sand.


——————————————————————

P.S.

If you’re reading this and something in here hits a little too close to home…if you feel hopeless, isolated, overwhelmed, or like the darkness is closing in, please don’t try to carry that alone.


There is no shame in reaching out.


There is no weakness in asking for help.


And there is always someone who wants you here tomorrow.

If you are in crisis or having thoughts of harming yourself, please reach out immediately:


988 — National Suicide & Crisis Lifeline

(Available 24/7)


If you’re outside the U.S., contact your local suicide prevention hotline or emergency services.


Lean in.

Get help.

You matter more than you think, and the world is better with you in it.

Light Up & Lean In,

Joshua Stephens

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The Slow Burn: Kansas City Cigar FestivalThe Slow Burn: Kansas City Cigar Festival
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Last week, several of the Brolos and I attended the Kansas City Cigar Festival. The festival was Saturday, but we decided to make a weekend out of it. Because apparently a bunch of grown men with an unhealthy amount of cigars can't simply arrive at an event, attend it, and go home like normal people.


We left Dallas around 6-ish Friday morning and pulled into Kansas City around 4:45 that afternoon. In between were gas stations, snacks, questionable decisions, lunch at Bite Me BBQ in Wichita, and a quick stop at Old Town Cigars. Shoutout to Old Town, by the way. They had an awesome selection of boutique cigars, including some of the old-school Metapas from before Foundation rebranded them as Aksum. Those aren't exactly sitting on every shelf anymore.


But I'm getting ahead of myself.


Shawn arrived at my place a few minutes late and blamed traffic. In his defense, he wasn't lying. 380 in the morning is a complete nightmare. North Texas has grown at a ridiculous pace, and it seems like no amount of construction can keep up. Every road is simultaneously being expanded and somehow getting worse.


We loaded Shawn up and headed to a bougie neighborhood in Prosper to grab Justin. We made it through the gate, pulled up to the house, and there he was...sitting in a camp chair, bags packed, already smoking a cigar.


It was a sight for sore eyes.


Naturally, we immediately started roasting him for not even making it to 6:00 a.m. before lighting one up. His defense was that he was "afraid he would be left out." Justin is the newest cigar smoker in the group, but the man put the first number on the board that weekend. Kudos.


Next up was Mr. Babyface himself, Mark. Picture this: it's roughly 5:30 in the morning and Mark is standing outside next to his truck, bags packed, looking like his parents just told him they were taking him to Disney World. Everybody was ready. And for the next eight hours, we absolutely destroyed my car.


Four men. A few boxes of cigars. Windows cracked. Ash everywhere. I don't think it will ever smell the same again. But that's the price you pay for making memories around something you love.


We put Justin in charge of picking lunch.


This was our first mistake.

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A reflection on Maine and the fear, pressure, and freedom that come with finally letting go of something you created.

Heritage: Recently, I’ve been thinking quite a bit about heritage and what that word actually means to me.Heritage: Recently, I’ve been thinking quite a bit about heritage and what that word actually means to me.
Heritage: Recently, I’ve been thinking quite a bit about heritage and what that word actually means to me.

It’s an all-encompassing term.


There are the tangible things and the intangible ones. The personal and the cultural. Traditions, values, stories, recipes, land, names, beliefs, habits, and physical objects passed from one generation to the next.


Some things are handed to us intentionally.

Others just arrive.


Building Brolo has me thinking about heritage quite a bit.


The cigar industry, maybe more than most, loves heritage. Many brands benchmark their quality against generational pedigrees, old-world traditions, luxury positioning, or some combination of the three. Families who have worked with tobacco for generations. Names that stretch back a hundred years or more. Stories with roots deep enough to make whatever they're selling today feel connected to something much older.

And there's something beautiful about that.


But where does that leave a kid like me?


I didn't grow up with a mother and father.


There isn't some great family enterprise being handed down to me. I didn't serve in the Armed Forces, and the only time I was involved with law enforcement was usually in the back of a squad car.


What the heck is my heritage?


And if heritage matters so much, how am I supposed to compete with that?


So I started digging.


Not through ancestry records or old family photographs, but through the things that got me here. The memories. The scars. The people. The failures. The things I learned accidentally and the things life taught me, whether I wanted the lesson or not.


I started asking myself:


What makes Brolo, Brolo?


The first image that came to mind wasn't tobacco.


It was a hay bale.


I was probably six or seven years old.


During the summer, my Grandma would drop me off for a week at my birth mother's trailer in East Texas, back behind the Pine Curtain.


Every summer, I dreaded it.


My second stepdad was quite a doozy...a real piece of work. Abusive. Violent. Looking back now, I can see he was probably just an angry boy trapped inside a man's body.


But when you're six, you don't have that kind of perspective.


You just know you're scared.


They lived in the country....or, as East Texans pronounce it, the cunnnn-trrrryyyyyyyy.


The acreage seemed to stretch forever, with a little creek running along the back of the property. My mother worked all day as a nurse, and my stepdad worked as a carpenter, taking odd jobs here and there.

I don't remember him being particularly great at woodworking.


But the man sure knew how to rip a doobie.


Wherever they were, I wasn't.


Most days, I was on my own, traversing the countryside. Climbing hay bales. Jumping hay bales. Falling off hay bales.


And, eventually, crying next to hay bales.

I remember getting hurt out there once.

And I remember being angry with myself for getting hurt.


Scared because I didn't know if I'd be able to survive a sprained ankle, let alone another week unsupervised.


Broken because I was alone and hurting.

And nobody showed up that day to help me.


Although that was the first time I remember feeling it, it certainly wasn't the last.


Those experiences taught me independence.


Eventually, they also taught me control.

If nobody is coming, you learn to handle things yourself. You learn to anticipate problems. You learn not to need much. You learn how to survive.


Useful skills.

Until they're not.


Because somewhere along the way, independence can become isolation. Self-reliance can become control. And learning not to need anyone can leave you desperately wanting someone.


Maybe that's heritage, too.


Not everything passed down comes in a box.


A few weeks ago, I went to the doctor for a regularly scheduled checkup. Somewhere between the blood pressure cuff and the usual questions, she started asking about my family.


Heart disease?

Cancer?

Diabetes?

High blood pressure?


She was trying to understand my family history...to identify the things buried somewhere in my DNA that might eventually become part of my story.


In other words, she wanted to know:

What runs in your family?


It's a clinical question.

But I've thought about it differently ever since. Because a lot more than disease runs in families.


Work ethic runs in families.

Faith runs in families.

Temper runs in families.

Generosity runs in families.

Addiction runs in families.

The way we handle money. The way we argue. The way we love. The way we apologize....or don't. The things we celebrate and the things we refuse to talk about.


Somewhere along the way, all of it becomes inheritance.


We tend to romanticize heritage.


Grandpa's watch. Dad's old truck. Mom's recipe written in her handwriting. The family Bible with names and dates scribbled across pages yellowed by time.

And those things matter.


But heritage has a shadow side, too.


Some things are worth preserving.

Some things are worth restoring.


And some things need to end with us.


My childhood was a lonely one through no fault of my own.


As I got older, I started pursuing people.

At first, probably because I was afraid to be alone.


I was tired of being alone.

I was starving for belonging.

But somewhere in that pursuit, I discovered something much better than simply not being alone.


I found connection.


If this were one of my gospel-centered recovery pieces, this is probably where I'd spend the next thousand words talking about how human beings were created for connection.


And I believe that.


I believe true connection begins vertically...with God...and that healthy relationships with one another are a by-product of that relationship.


But that's another rabbit hole for another day.


Back to connection.


Because that's what Brolo is about.


Not heritage manufactured through some bullshit origin story.


Not luxury for luxury's sake.


Not pretending we've been making cigars since 1873.


Connection.


It's the early-morning text from a friend encouraging you to succeed while simultaneously making light of your many proclivities.


It's the random Tuesday-night HERF where, for whatever reason, the whole crew shows up, and you belly laugh until your face hurts.


It's an early-morning coffee where somebody finally stops saying they're "good" and tells you what's actually going on.


It's spending so much time smoking cigars together that you know your buddy's palate almost as well as your own. You know what he's going to love. You know what he's going to hate. And occasionally, you make a recommendation that he actually likes.


It's getting bombed by one of the Brolo's.


It's seeing the UPS truck turn onto your street....or maybe even chasing it down, and feeling that little dopamine hit because you know there's a box headed your way.


It's knowing that whatever ails you, somebody is rooting for you.


It's complete strangers finding each other in some random corner of Discord or Reddit, sharing a cigar through a screen, and eventually becoming friends in real life.


Those things probably don't sound like heritage.


At least not the way the word is usually sold to us.


There aren't any centuries-old family photographs.


No tobacco fields passed from father to son.


No crest.

No pedigree.


But maybe I've been thinking about heritage all wrong.


Maybe heritage isn't just about where you came from. Maybe it's about what you carry forward.


And maybe the things we weren't given are sometimes the very things we become most determined to give away.


I didn't inherit a great legacy of connection.


So I built my life around finding it.


And now we're building Brolo around giving it away.


Maybe that's my heritage.


Not the kind printed on the inside of a cigar box. Not a family crest, a famous last name, or some romantic story about generations of men who came before me.


It's messier than that.


There's some good in it. There's some bad. There are things I'm proud to carry forward and others I've spent most of my adult life trying to put down.


But all of it got me here.


And I suspect the same is true for you.


What's your heritage?


Not just where your family came from or the traditions you grew up with.


What did you inherit?

What runs in your family?

What did someone teach you without ever sitting you down to teach it?


What wounds shaped you?

What values stuck?

What traditions still matter?


What parts of the people who came before you can you see when you look in the mirror?


And maybe more importantly:

What are you doing with it?


Because at some point, we stop being merely the recipients of heritage.


We become responsible for it.

We decide what gets carried forward.

What gets restored.

What gets rewritten.

And what ends with us.


Heritage isn't just the story of the people who came before you.


It's happening right now.


In the way you raise your kids. The way you love your spouse. The way you treat your friends. The work you put your hands to. The things you make time for. The things you refuse to compromise. The table you build and the people you invite to sit around it.


Whether you realize it or not, you're leaving something behind.


When I think back to that little boy sitting alone in East Texas, hurt and scared and wondering if anybody was going to show up, I can't change his story.


Nobody came that day.


But I can decide what I do with what he gave me.


Maybe that's why showing up matters so much to me now.


Maybe that's why the table matters.

Maybe that's why connection matters.

Maybe that's why Brolo exists in the first place.


So maybe the better question isn't simply:

What's your heritage?


Maybe it's:

What will someone else inherit because you were here?


What impact have you made, or lack thereof?


And maybe that's convicting...if so...that was my intention.


Kaitlyn and I don't make cigars to avoid life. We make cigars to fully embrace it. The good, the bad...the hurt and the wins.


All around a shared smoke.

About This BlogAbout This Blog
About This Blog

I wrote this back in 2017 and never published it. I found it again. And reading the words of the man I was has been an uncomfortable experience. This post is a multipart post about shame and where we can find hope. Stay tuned for the next post in the series...

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