The Rebirth of Cigars and the Founding of Drew Estate

by Juan Panesso
A man with glasses and a beard sits in a leather chair while smoking a cigar


Cigars were once a fairly common vice (let's say in the first half of the 1900s). But after reaching a peak in 1964, sales started to fall. This was partially brought on by the US Surgeon General's report on smoking and health. Another reason was that young adults and "teenagers" (a term that had just been coined at the time) saw cigars as their parents' vice; to the younger crowd, cigars were simply uncool.

Why Did Cigars Have to Be Reborn?

As a result, the sale of cigars decreased steadily over time, from nine billion in 1964 to a pitiful two billion in 1992. Due to the surgeon general's report and the associated image issue, many Americans came to associate cigars with vices of lowlifes, degenerates, and obstinate traditionalists.

Could Good PR Bring Cigars Back?

Things began to turn around in the 90s. The reason? Well, it all stems from the most well-known cigar to emerge from a hole in history! Monica Lewinsky discussed every sweaty detail—and we do mean every detail—of her relationship with then-President Clinton, including a well-known encounter with a cigar. It was 1998. Long before then, cigar sales began to rise.

So what happened in ’92?

Cigar Aficionado, believe it or not!

Even though it can be a little stuffy at times, the contemporary cigar world's cultural compass launched and then assisted in ushering in a revival of cigar smoking. 

Two young surfers were able to paddle out to and then ride this new wave of cigar popularity as it grew to be the powerful 50-foot wall of water we are all currently riding.

Who Needs a Pedigree?

Cigars are an industry like any other, and so generational pedigrees have always been powerful. If your great-grandfather farmed tobacco, your grandfather rolled cigars, and your father oversaw the international distribution of a beloved local product, you’re assumed to be next in line. You’re in without even trying.

For Drew Estate, it was different.

At Oneonta State University in the early 1990s, Jonathan Drew and Marvin Samel were fraternity brothers. There’s no Cuban lineage. There were no cigar-leaf mobiles hanging over their cribs. They hardly knew any Spanish at all.

Nevertheless, they introduced Drew Estate in 1996 under the slogan "The Rebirth of Cigars" despite all of that. Can you believe that? These guys were gutsy. How much business knowledge could they possibly have?

As it happens, more than enough to completely dominate the industry.

A Kiosk in the World Trade Center

At the World Trade Center in 1996, Drew Estate consisted of just two men and a 4' x 4' cigar kiosk. The Drew Estate team was there to supply cigars to NYC's burgeoning business titans as the cigar revival was just beginning to pick up. But there was a problem. Actually, there were lots of problems:

  1. Rent was inordinately high.

  2. They would run out of cigars all the time as demand raced ahead of supply.

What they needed most was stability.

Do you know what most men would do in this circumstance? Berate your suppliers while you wait for things to improve.

Do you know what most guys wouldn’t do? Launch a cigar line with the help of a local roller.

They called it Vieja Habana.

The Drew Estate website claims that a never-say-die mentality was one of the key factors in the brand's success. Clearly, it was operative at that point.

But things hadn’t even begun to get wild.

The “Crazy Gringo” Moves to Nicaragua

View from the roof of the Cathedral-Basilica of the Assumption of the Blessed Virgin Mary in León, Nicaragua

In 1998, Jonathan moved to Estelí, Nicaragua to start making cigars. He knew hardly any Spanish. He was just a random white dude with a shitload of guts who walked out the door of his NYC apartment and headed south one day. 

It all began modestly with a small sum of money, a small number of rollers, and limited quantities. Nevertheless, cigars were produced and distributed.

Marvin, the other member of the founding duo, was frantically trying to raise money for the revival of cigars while Jonathan was attempting to make it in Nicaragua. He would hit up anyone he could for money to feed the beast. And those who have started a business with a "short runway"—a term used in business development for having too many goals but insufficient resources—know that the beast eventually becomes hungry.

Do you know what you give a hungry beast? Acid!

Screw Tradition

In 1999, Scott “ACID” Chester was an artist in industrial, urban, graffiti, and motorcycle art. You might be asking, “Are those media or art types?” Yes. The answer is yes. Scott hooked up with the Drew Estate dudes and would eventually become the creative heart of the brand imagery and more. 

The team was also actively tinkering with cigars during that year, using Chinatown-sourced oils and botanicals to see if they could produce anything interesting. Many of the blends were disgusting, but a few were actually pretty cool. The boys launched these experiments with Scott’s artistic help as the ACID Infused Cigar Brand, which now features dozens of different cigars that offer innovative flavors and are made with interesting processes. 

The Natural line was introduced in 2000, and it was launched from a vintage yacht off the coast of Manhattan.

The DE team introduced the "AMBROSIA tobaccos exotica" infused cigar in 2002. Isn't that insane? Absolutely nothing like the cigars your grandfather would have smoked! They were right on the money, though, and Drew Estate kept climbing.

In 2004, Drew Estate opened a Miami office, and Steve Saka was brought on board to bust butts like a “drill sergeant.” It was very effective (we love the smell of accountability in the morning).

Ultimately, despite all of its success, Drew Estate was expanding too quickly to keep up with demand at all of its factories. Something had to be done.

It shouldn't come as a surprise that the boys' next move was a risky one.

The Biggest Damn Cigar Factory in Nicaragua

The Drew Estate boys officially opened La Gran Fabrica in 2006. The largest in Nicaragua and among the top five largest hand-made cigar factories worldwide, it has 96,000 square feet of cigar excitement. 

The sale of the business to Swisher International in 2014 marked the triumphant end of the first major arc of the Drew Estate story, which had been unfolding for eight years.

A strange marriage, right? 

When you think of Swisher, you probably don't picture anything like the properties that the Drew Estate men were trying to sell. 

You probably weren't shocked, then, when they rehired Jonathan Drew as president in 2017. He just couldn’t stay away.

No doubt, another rebirth is underway.

Whichever way the company goes, we know this will stay true for tons of cigar smokers and certainly for our team: When Drew Estate drops a cigar, we don’t ask questions. We just grab a lighter.

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