Big News in the Cigar World This Week

A surprise, a story, and big cigar news.

In partnership with

Sometimes a cigar doesn’t impress you the first time — kind of like a movie everyone swears is brilliant, but you watch it half-distracted and think, Really? This is it? That was me a few months ago with a particular stick that left me feeling
 politely underwhelmed.

Last week, I found another one resting in the humidor, looking at me like it wanted a rematch. New day, clearer palate, slightly better mood — and suddenly this cigar showed up like it had been taking performance-enhancing naps. Flavors opened, the burn straightened out, and I swear it even seemed a little smug about it.

Cigars are funny that way. Give them time, give yourself time, and sometimes the same smoke becomes an entirely different story.

The Forgotten Cigar Capital That Once Ruled the World

Most cigar lovers picture Havana or Santiago when they think of the cigar capital of the world. But for about forty incredible years, the true champion wasn’t an island at all — it was a humid Florida swamp that had no business becoming anything important. And yet
 it became Ybor City, the most unlikely cigar empire in history.

🌮 A Cuban Visionary Picks
 Florida?

In the 1880s, Cuban entrepreneur Vicente MartĂ­nez-Ybor needed a new home for his cigar factory.
Cuba was unstable. Key West was cramped. And he wanted his workers to have a real community — not just a place to sleep between shifts.

So he picked Tampa.
Not modern Tampa. Not beaches-and-palms Tampa.
No — mosquito-infested, swamp-heavy, “are you sure about this?” Tampa.

But somehow
 he absolutely nailed it.

đŸ§± A City Built on Tobacco and Hope

Within a decade:

  • Massive brick factories lined the streets

  • Ships brought in leaf from Cuba

  • The air smelled like warm, curing tobacco

  • And thousands of Cuban, Spanish, and Italian immigrants arrived to build a better life

    These weren’t workers punching clocks. These were artisans who treated tobacco like a craft, not a commodity.

    đŸŽ™ïž Inside the Factories: The First Podcast

Walk into a factory in 1900, and you’d hear a hum — part machinery, part human rhythm, part
 literature.

That’s because of the lector:
A professional reader perched on a platform, reading:

  • Newspapers

  • Political essays

  • Classic novels

  • And probably the occasional spicy chapter someone pretended not to enjoy

The lector wasn’t entertainment — he was education, community, and culture all rolled into one. Joe Rogan wishes.

At its peak, Ybor City produced over 500 million cigars a year.
Half. A. Billion.
All by hand.

đŸ•°ïž The Golden Age Fades

Like all great eras, this one had an ending.

  • Machine-rolled cigars got cheaper

  • Cuban tobacco became harder to source

  • Immigration patterns shifted

  • And one by one, the factories went quiet

    Ybor City went from a roaring industrial center to a shadow of its former self.

🧭 Ybor City Today: A Living Memory

And yet
 the soul remains.

Walk the streets, and you’ll still find:

  • Historic brick factories

  • Cuban cafĂ©s with the smell of strong coffee

  • Cigar shops that honour old-school traditions

It feels like a living museum, where the past hasn’t vanished — it’s just resting, like a cigar waiting to be lit again.

❀ Why This Story Matters

Ybor City reminds us that cigars weren’t built by corporations — they were built by:

  • Immigrants

  • Craftspeople

  • Families

  • Communities

    Every cigar you enjoy today carries a little of that history in the leaf.

The “Buy Two” Trick Every Smoker Should Try

Here’s a simple experiment that can change the way you judge cigars: always buy two.
Smoke the first one right away — not for perfection, just for a baseline. Then let the second rest in your humidor for a week or two. Same cigar, same blend
 completely different experience.

Fresh cigars can taste sharp or tight, especially if they’ve been travelling. But a rested cigar? The flavors relax, the burn steadies, and suddenly that “pretty good” stick becomes a sleeper hit.

Try it once, and you’ll see: time isn’t just a factor — it’s an ingredient.

7 Ways to Take Control of Your Legacy

Planning your estate might not sound like the most exciting thing on your to-do list, but trust us, it’s worth it. And with The Investor’s Guide to Estate Planning, preparing isn’t as daunting as it may seem.

Inside, you’ll find {straightforward advice} on tackling key documents to clearly spell out your wishes.

Plus, there’s help for having those all-important family conversations about your financial legacy to make sure everyone’s on the same page (and avoid negative future surprises).

Why leave things to chance when you can take control? Explore ways to start, review or refine your estate plan today with The Investor’s Guide to Estate Planning.

Old Forester Drops a New Beast of a Bourbon

Old Forester just celebrated Repeal Day the way any self-respecting distillery should — by releasing something loud enough to wake the neighbours. Their newest limited edition, the 117 Series Prohibition Era Still Proof, clocks in at a feisty 130 proof. Yes
 130. As in: “sip carefully or time-travel unintentionally.”

What makes it cool?

  • It’s inspired by the whiskey Old Forester legally produced during Prohibition for medicinal purposes — because apparently “doctor-prescribed bourbon” was totally a thing.

  • The flavor profile leans punchy: big oak, heavy spice, toasted wood, and that old-school “don’t mess with me” attitude.

  • It’s a limited release — translation: collectors are already circling like hawks over a ribeye.

If you’re into bourbons that bring history, heat, and the possibility of growing a temporary chest hair or two, this one’s worth keeping an eye out for.

Maduro + Aged Rum: A Dessert Without the Dessert

This week’s pairing is a can’t-miss classic: a rich Maduro cigar matched with a smooth, aged dark rum. It’s one of those combinations that feels effortless — deep, sweet, and warm, like the flavor equivalent of dimming the lights and exhaling after a long day.

đŸ„ƒ Try These Rums

  • DiplomĂĄtico Reserva Exclusiva — syrupy caramel, warm spice, dangerously sippable

  • Plantation XO 20th Anniversary — tropical fruit, vanilla, toasted oak

  • Flor de Caña 12 — cleaner profile with molasses, cocoa, and gentle oak

🚬 Pair With These Maduro Cigars

  • Arturo Fuente Double Chateau Maduro — classic, balanced, chocolatey

  • Oliva Serie V Maduro — bold espresso, dark sweetness, slow burn

  • Alec Bradley Black Market EstelĂ­ — spicy-sweet, earthy, great with rum

💡 Why This Works

  • Maduro cigars deliver dark chocolate, espresso, and natural sweetness

  • Aged rum brings caramel, molasses, fruit, and spice

  • Together, they create a smooth “liquid + leaf dessert” that’s rich but never heavy

If you’ve never tried a cigar-and-rum pairing, this is the one to start with — low effort, big payoff, instantly relaxing.

Crowned Heads Announces Its TAA Exclusive 2025

Crowned Heads is back with a new limited-run release for 2025, and this year’s TAA Exclusive is shaping up to be a standout. Rolled at the D’Hatuey factory in Estelí under Eradio Pichardo, the cigar comes in a 5⅝″ × 54 robusto extra, dressed in a dark and oily Ecuadorian Habano wrapper. Underneath, it features an Ecuadorian Connecticut-seed binder and all-Nicaraguan fillers, giving it a profile the company describes as medium-plus with richness and balance.

Only 750 boxes of 10 were produced, with flavors expected to lean toward cream, dark chocolate, toasted nuts, subtle sweetness, and warming spice. If you enjoy Crowned Heads releases that combine tradition with a little attitude, this one’s worth hunting for before it disappears.

đŸ€ Closing Thoughts

From My Humidor to Yours

Before we wrap this week’s edition, I want to leave you with something simple: cigars are better when they’re shared — stories, too. Every week, this little community grows a bit more, and it reminds me why I started Smoke Signals in the first place. Not for reviews. Not for ratings. But for the conversations that happen when people slow down, light up, and actually talk.

So this week, I’d love to hear from you:
What cigar surprised you the most — good or bad — when you gave it a second chance?

Hit reply if you have a story. I read every one.

Until next week

Slow draws, good company, and better days ahead.

Subscribe to keep reading

This content is free, but you must be subscribed to Smoke Signals to continue reading.

Already a subscriber?Sign in.Not now

Reply

or to participate.