The Second Worst Cigar I Ever Smoked; A Story About Cigars, Ego, and Brotherhood

Some things can only be learned the hard way.

As a writer, I wage a lot of wars against a blinking cursor.

I get caught somewhere between what I want to say and what I think people want to hear. And I’m beginning to believe that’s a dangerous intersection.

Beneath a Nicaraguan moon, hidden behind a mosquito net, tree frogs wage war against my sleep. Their calls echo through the jungle like ladies of the night working a truck stop, each one louder than the last. Halloween Moon Crabs scatter across the ground beneath our cabana. I have to pee...but I'm not getting out of bed. Nature can have this one.

We all have a collection of "if only" moments….roads not taken, mistakes we'd undo, opportunities we missed. But the longer we stare into the rearview mirror, the more likely we are to miss the blessings sitting right in front of us.

I knew a lot of people, but I wasn't truly known by anyone. That realization changed everything. What followed was addiction, recovery, reinvention, and another chance to choose the life we wanted to build.

The ocean was turquoise. The tacos were endless. Paradise was perfect. Yet all I could think about was tomorrow. Sometimes the dreams you’ve prayed for have a way of exposing what you really believe about yourself.

PSA: This is going to be a sappy post. I tried to write my way out of it, but here we are.

Born in 1983, I grew up during a strange and wonderful time to be alive.

I remember summer mornings when parents encouraged you to leave the house and didn't expect to see you again until the streetlights came on. Nobody had Ring cameras. Nobody was posting

neighborhood warnings on Facebook. We weren't worried about the "big bad wolf" down the street. We had one family phone hanging on the kitchen wall...unless your parents were absolute ballers and paid for a second phone line.

Weekends were spent at sleepovers. We'd roam the aisles of Family Video or Blockbuster looking for the perfect movie. If we got lucky, we'd stop by Little Caesars next door and grab a Bigfoot Pizza before heading back to somebody's house.

Late nights meant MTV, TRL, Beavis and Butt-Head, and Twisted Metal tournaments that felt like they carried the weight of the world. Mellon Collie and the Infinite Sadness played through cheap speakers while we argued over who cheated and who got robbed.

Then, seemingly overnight, everything changed.

Dial-up.

24k modems.

The internet exploded.

Half my childhood happened before the online world. The other half happened after it arrived. The soundtrack of my life changed from guitars and arcade machines to the sound of AOL connecting.

You know the one.

Suddenly there were chatrooms. Screen names. Endless possibilities. Every conversation started with the same question: A/S/L?

As a tweenager, I found myself staring into a world I wasn't quite ready for.

I came from humble beginnings.

My Grandpa T-Mack…better known as "Smokey" Stephens…passed away around the time I was born. My birth father was never in the picture. My birth mother was just a kid herself, carrying a responsibility no fifteen-year-old should have to carry alone.

I spent time in foster care and bounced between homes before eventually landing with my grandmother, Joyce.

Joyce was a firecracker.

She worked at the county courthouse, where she met my grandfather. But by the time I came along, life had taken its toll. COPD. Asthma. Brain aneurysms. Most of my memories of her involve oxygen tubing and a wheelchair.

But none of that stopped her.

When she gained custody of me, she and her husband Bobby owned a little honky-tonk in East Dallas called The Junkyard Club.

To a kid, it was magic.

The place wasn't fancy. About 2,500 square feet. A full-service bar and kitchen. Cheeseburgers and fries served in hubcaps. Pool tables. Shuffleboard. An Elvira pinball machine. A Galaga cabinet tucked in the corner. Live music every Friday and Saturday night.

Grandma would bring me to the club after school while she worked the books.

I'd spend hours wearing out my wrists on Galaga while the cook fed me an endless supply of grilled cheese sandwiches. Every plate came with maraschino cherries.

The regulars all knew me.

One afternoon, an older gentleman dared me to eat a handful of jalapeños. Since Grandma didn't raise a quitter, I accepted the challenge. A few seconds later, I was sprinting through the bar screaming while tears rolled down my face. The regulars laughed. Grandma never looked up from her paperwork.

But the coolest thing in the entire place wasn't the arcade games. It was the school bus. After getting past security, you'd walk inside and immediately see it sitting on the right side of the club. A full-sized yellow school bus.

Somehow it had been disassembled, moved inside, and put back together as the centerpiece of the bar. Inside were booths and tables. But at the very front, beside the driver's seat, was The Table.

You could look out over the entire room from there.

It wasn't elevated much, but it felt like it was. To a kid, it looked important. It felt important. Like some kind of white-trash luxury suite. A little reserved sign sat on the table.

But here's what I eventually learned:

It wasn't reserved for the people with the biggest wallets.

It wasn't reserved for the loudest people.

It wasn't reserved for the owners.

It belonged to the regulars.

The people who knew everyone by name.

The ones who threw twenty dollars into the jukebox and played Creedence Clearwater Revival until everyone else was sick of hearing it.

The ones who showed up.

Again.

And again.

And again.

They had earned a seat at the table simply because they were part of the story.

Early in the evenin', just about supper time...

Down on the corner, out in the street...

Willy and the Poor Boys are playin'...

That was our place.

A place to know people and be known by them. As a kid, I didn't have the words for it. I just knew it felt different.

The smell of cigarette smoke hanging in the air.

The beer-soaked bar mats.

The sound of live music echoing through the room.

The laughter.

The conversations.

The feeling of belonging.

I felt connected.

When my grandfather died from cancer, Grandma sold the club. Eventually the building became something else. These days it's called The Lone Star Cafe. It's still there.

Back before I got sober, I'd stop by every December 21st…Joyce's birthday. I'd order her favorite drink. A margarita. No mix. Just tequila, fresh lime juice, a salted rim, and a lime wedge. Then I'd feed a few dollars into the jukebox and play CCR.

The school bus is long gone now. But when I close my eyes, I can still see it.

The band is playing. People are laughing. Someone just beat my high score on Galaga. Another guy is staring at Elvira. Pool sharks are running the tables. Sherry the bartender slides me another cup of maraschino cherries.

For a moment, life is exactly as it should be.

That's what Back Booth is about.

Back Booth is our boldest core cigar. A 5x50 Robusto wrapped in Mexican San Andrés. Medium-plus in strength. Full of character. Rich, dark, and unapologetic. My friend Austin described it as tasting like the best barbecue bark he'd ever had. Granted, he's from New York, so we'll take that review with a grain of salt.

But he wasn't wrong.

Because barbecue and cigars have a lot in common. Neither can be rushed. The best briskets aren't built in minutes. The best friendships aren't either. Both require time, patience, smoke, and a willingness to stay put longer than everyone else.

That's what the Back Booth represents.

Not exclusivity.

Not VIP status.

Not some velvet-rope version of cigar culture.

It's a seat that's available to everyone.

But it takes time to appreciate why it's special.

It's for the people who understand that the best conversations happen after everyone else has gone home.

The ones who know that community isn't built overnight.

The ones who keep showing up.

Again.

And again.

And again.

So pull up a chair.

Look out over the driver's seat.

Watch the crowd.

Catch the glow of the neon signs.

Listen as some up-and-coming band works their tail off trying to move the room.

Then take a look at the person sitting across from you.

Because moments like those don't last forever.

And that's exactly what makes them worth savoring.

So Light Up & Lean In.

Enjoy the moment because the "good 'ole days," well…you don't know you are in them until they are gone.

Growing up is learning what opportunities to say "no" to. This week, that meant walking away from a lucrative offer, embracing the uncertainty of building Brolo, and realizing that regret is far scarier than failure.

Everyone wants to know the factory, binder, and filler. We get it. But we believe great cigars are remembered for the moments they create, not the spec sheets behind them. Here's why we're choosing experience over credentials.