The Second Worst Cigar I Ever Smoked; A Story About Cigars, Ego, and Brotherhood
We did it.
Well… some of us did.
Although it was borderline medieval torture, Shaun finished The Woody by Oscar, a 21x80 Honduran puro that takes somewhere between four and seven business days to smoke, depending on lung capacity and will to live. Patrick from Halfwheel clocked it at seven hours. Shaun looked like he’d aged seven years.
Me?
I made it twenty-five minutes.
Getting the thing lit required lungs forged in a CrossFit volcano. Someone produced a blowtorch like we were welding farm equipment. Even with all the right tools at my disposal, my head started pounding, my eyes watered, and my soul quietly whispered, “You don’t have to prove anything to these people.”
Then came the draw.
Or lack thereof.
After enough wheezing to qualify for a medical study, Shaun handed me his sacred relic: the PerfecDraw.
Now, one thing you should know about Shaun, the man loves cigars. Knows cigars. Owns cigars. Has gadgets for his gadgets. If cigars had a Costco membership program, he’d be platinum.
He calmly explains, “You gotta be careful with this thing, or you’ll punch through the wrapper and ruin the cigar.”
Naturally, I immediately ignored him.
Point. Center. Push.
Ten seconds later, my cigar turned into a flute.
A clean, glorious hole straight through the side.
Was I mad?
Nope.
I was relieved.
I tossed that log of suffering into the abyss, reached into my humidor, and lit something balanced… intentional… humane.
And I sat there smiling while everyone else committed to their bad decisions like war veterans.
I won’t lie…watching grown men suffer through a novelty cigar while I enjoyed myself was carnally refreshing.
And that’s when it hit me:
I didn’t want to smoke The Woody.
I wanted the idea of smoking it.
The story.
The photo.
The bragging rights.
The “remember when we survived this” badge.
Somewhere along the way, the experience became less about enjoyment and more about endurance.
Less about flavor…more about flexing.
Less about connection…more about completion.
It wasn’t a cigar meant to be enjoyed.
It was a cigar meant to be conquered.
And we do this with life all the time.
We romanticize things from a distance:
The job.
The title.
The relationship.
The lifestyle.
The business.
The version of ourselves we think we’re supposed to become.
We picture the highlight reel. The applause. The moment at the top of the mountain.
Nobody daydreams about:
The headaches.
The nausea.
The tools just to make it barely functional.
The quiet realization at hour three that you chose wrong.
Sometimes the dream is real.
Sometimes the dream is just a 21x80 mistake wrapped in good marketing.
Here’s the uncomfortable truth:
Quitting the wrong thing is often braver than finishing it.
Punching that hole felt like failure for three seconds.
Then it felt like freedom.
I reached into my humidor and grabbed something balanced. Something thoughtful. Something made with intention. Something that didn’t require suffering just to prove a point.
And suddenly everything was good again.
The reason I smoke cigars in the first place came back.
It’s about smoking the right thing.
The cigar that invites you to stay.
Not survive.
The kind that doesn’t dare you to endure…
but asks you to slow down.
Because there’s a difference between:
“I finished it.”
and
“I enjoyed it.”
Life’s too short to confuse the two.
Sometimes wisdom looks like grit.
Sometimes it looks like a hole in the side of a cigar, and the humility to choose better.
And here’s the truth:
There’s no medal for suffering through bad cigars.
No parade.
No sash.
No secret society whispering, “Thank you for your service.”
The real win?
Putting it down.
Lighting something better.
And rejoining your people.
Laughing while your buddies stubbornly commit to the bit.
Borrowing tools you don’t know how to use.
Roasting each other for rookie mistakes.
Watching grown men debate draw resistance like it’s constitutional law.
Not perfection.
Not endurance.
Not luxury cosplay.
Just shared smoke.
Shared stories.
Shared moments.
Preferably over something enjoyable.
And if you ever turn your cigar into a woodwind instrument along the way…
Welcome to the brotherhood.
