The founder and owner of Principle Cigars, Darren Cioffi, may not remember his first premium cigar experience, but his extraordinary designs and extensive portfolio are challenging to forget. Cioffi, a self-proclaimed “paper” guy and cigar guy, entered the cigar life by collecting vintage cigar bands. His love of cigars grew with his passion for antique graphics and design. He talked to Cigar Life Guy about the joys of appreciating aesthetics, the pains of competitive slow smoking, and bringing the Principle brand home to the United States.

First Premium Cigar Experience

Cigar Life Guy: Tell me about your first premium cigar experience.

Darren Cioffi: I don’t have one. I am trying to remember when my first cigar was. There was no “aha” moment. I just eased into it. It was a result of travel and being around people who were into smoking and working in the Caribbean. It just became something I was doing. I honestly do not remember.

Vintage Labels and Design

Cigar Life Guy: Your interest in history and antiques started in high school. Tell us how you found vintage cigar labels and the tobacco industry.

Darren Cioffi: I started as a high school sophomore and dealt with three-dimensional things like clocks and books. I was doing more and more of that on Long Island, where I grew up. After that, I started selling at the 26th Street Antique Market in New York City on the weekends.

During the week in the summer, I started going down to Pennsylvania to the markets and the auctions to look for stuff to sell in New York. It was before I could drive, and I was in PA somewhere. My mother was driving me, and she saw this goofy shop and said, “Hey, why don’t you check out that place?”. I said, “No, just keep driving. You never find anything in shops.” 

To this day, I don’t know why she insisted (she didn’t care about this stuff), but finally, I said, “Yeah, let’s check it out.” I went in and just got lost. 

The guy was a paper dealer, and my life changed then. I went 100% into paper. That looks like advertising artwork, financial documents, stocks and bonds, autographs, and photography. But one thing that guy mainly had was cigar labels. The labels immediately fascinated me. They were a hundred years old and were Stone Lithographs. The cigar labels were stunning and rare, even though you could find them in groups.

I just went hardcore. From there, I started going to Europe looking for cigar labels and then going around the Caribbean. While there, I started smoking cigars. 

It all happened at the same time. I was buying and selling tobacco-related artwork, and I also started dealing in vintage cigars, mostly because I was interested in the packaging and the design. Then, I realized that people were smoking that stuff, too. 

The 1870s to 1930s is vintage to me. It’s a passion that grew simultaneously on all fronts. These days, I’m mainly dealing with other paper, not so much cigar stuff, but I’m still acquiring it. I have an enormous amount of it. I’ll start working through and selling some of that stuff someday.

Principle Cigars Band Designs and Presentations

Cigar Life Guy: You dealt with tobacco artwork before you smoked cigars, and Principle Cigars’ band designs and presentation are innovative and distinct. Why are aesthetics as essential to branding as taste?

Darren Cioffi: I’m a guy who is into antique graphics first and cigars second. From that perspective, I know more than what’s sound design and what’s terrible design. I know what works from a collector’s perspective. I understand what people desire and what they want to own in terms of graphics. Much of that translates to our inspiration for brand design. 

We always create products that look like they could be from a certain period, not just in the period’s style. Many people who know us think, “Oh, Principle Cigars is Art déco” because our Aviator series is Art déco. It’s true, but even within Art déco, many schools exist. Aviator is American late 1940s industrial era Art déco, whereas Accomplice is more 1930s French style with some Art nouveau holdovers. Petits Provocateurs is a hardcore French turn-of-the-century Art nouveau, like perfume model branding. Angelique is 1960s style. Martinique is 18th Century Island Colonial.

We work with many styles and stay as accurate to them as possible. We desire to make the product look like it could be from that period on the shelf. If we do that, it will be attractive to educated consumers who understand the design and those who lack the knowledge but find it appealing. It’s showing them something they haven’t encountered in their regular life. But great design is great design. It will speak to them on some level.

There’s absolutely nothing wrong with enjoying product design. You go to a liquor store and see how many innovative wine bottle labels there are. Sometimes, I smoke a cigar because I appreciate the design. I’m not saying that it’s guiding my decision, but why can’t I take joy in the attractiveness of a product I’m consuming, as well as the essential attributes of that product, like taste and performance?

The Principle Cigars Portfolio

Cigar Life Guy: You are known for not taking shortcuts when blending tobacco. What does this mean to you, and what sets Principle Cigars apart?

Darren Cioffi: This is a hands-on project. I make cigars in seven different factories now, and I’m involved with every leaf in all of them. We work with other people because they all have different strengths. From the design to the blending to the mechanics to the positioning of everything behind this product, it’s my passion. It’s not a guy knocking on the door of a factory, selecting a blend to market. I don’t care about the marketing. Smoke my cigars. Sell my cigars. Don’t do it. It’s fine. I have a long-term approach. I do this because I love it.

I’m never out there hustling. It’s all about creating a product that is as beautiful as I can. The product will work for me if I stay true to that principle. For people who take the time to process our cigars- those who pay attention to it, look at it, taste it — it’s evident. I never like to be in the position where I tell people, “Hey, smoke this because…” But of course, I want people to try my stuff, and I would like to think the product speaks for itself when they do.

Principle Cigars Portfolio of Premium Smokes

Cigar Life Guy: Principle boasts a broad portfolio of cigars. Tell us about some of your favorites.

Darren Cioffi: We do a lot of stuff for a smaller company. That results from being passionate and wanting to create different things constantly. When we have something small and interesting, we want to share it with people. 

Sometimes, we have products we don’t promote because we know we will only make a few thousand cigars. They’ll get out there to some folks and those paying attention, but if we promoted and distributed them properly, people would only sometimes experience them. We’re in a lot of different countries. The byproduct of how we do things results in a wide product range.

We have something called the Cocktail Collection, a series of cigars designed to pair with five different cocktails from different periods with branding specific to those periods. But we scrapped it over the last few years because we have so much stuff coming out. Instead, we use the Cocktail Collection as an umbrella to sporadically release cigars within the series. 

We just came out with the Tiki, the Mai Tai companion, and I am chain-smoking that cigar. There’s a Robusto that’s widely available, and then there’s a Toro. We have a co-branded space with Industrial Cigar Company in Frisco, Texas, so we created a Tiki Toro for the new room — a cocktail lounge called Fuselage.

It’s all I’m smoking these days. It’s bright and effervescent and just as gorgeous as can be. 

Another cigar we released, but we have yet to make a big splash about it because we only made about two thousand cigars, was a Tenth Anniversary Aviator called the Espoir. It’s a 9.5 by 46 gauge cigar. We made these in January 2023, so they have exactly one year on them now. 

I’m a fast smoker, but I like big cigars. I like cigars that last a long time. The problem is that larger cigars with relatively large ring gauges can eat up if you puff them like I do. So I made this 9.5 by 46. It’s complex. It’s a rich Aviator, as you might expect, but its long size and narrow ring gauge regulate the heat level where I can puff the hell out of it for two hours and maintain the flavor. I don’t lose it to overheating like other larger cigars. So the Espoir and the Tiki are my two go-to’s.

Cigar Life and the Challenges of “Slow Smoking”

Cigar Life Guy: You have traveled worldwide and spent time with some exciting and eccentric people. Who is the most interesting person (or people) you have shared a cigar with?

Darren Cioffi: I don’t have a good answer for this. You never know when you’re going to find inspiration from people. When you do what I do, you meet many people. 

I always admire those who have the brainpower to categorize every person they’ve met and remember what pleasant conversation they’ve had with them or what cool thing they were talking about. But I am not that guy. I show up at a place I have been a year or two before, and I might recognize the faces and have vague recollections. However, I could improve in categorizing everyone’s names and what we discussed. The benefit of doing this is you meet a hell of a lot of people. 

You never know when the spark will light and a casual conversation in a cigar lounge will become exciting and unique. Thankfully, it happens more frequently than you would expect.

A First for Cigar World Championship

Cigar Life Guy: You were the first American to win the Cigar World Championship. What was that experience like, and why is it essential to savor a premium cigar?

Darren Cioffi: It’s a different activity. It’s not that I’m just so great at it. For whatever reason, I can do it. I went, not knowing I could do it, and I won. Because I won, I kept doing it for a while. It’s part of why we’re a primarily European cigar brand today. It gave us enormous publicity when the company was only a few years old. But it’s a different activity.

The slow smoking you do to compete isn’t smoking to savor the cigar. When you’re smoking a cigar, even slowly, to experience the cigar, you need all of the tobacco burning simultaneously, so you are getting that complete recipe of wrapper, binder, and fillers all combusting and combusting at a low temperature. So it’s not that you’re smoking slowly to maximize enjoyment; you’re smoking appropriately to do so. And that level of appropriateness changes based on the combustibility of the blend. Ideally, you’re blending a cigar so it combusts in unison and correctly delivers the blend recipe.

But anyone can smoke too slowly. If you’re not paying attention to your cigar, you’re tunneling and burning the tobacco inside. You can tell. The taste goes away because you’re not getting the recipe. Smoking slowly for enjoyment — too slow is too slow. 

You have to smoke so that everything is burning, but you’re also maintaining temperature. When you’re smoking slowly to compete, you’re just smoking a dot, and you’re moving that dot around the cigar. At times, you’re intentionally smoking on the inside, and then you’re going to move that burn to the outside. 

You don’t want to burn the entire cigar at the same time as you would if you were smoking for enjoyment because then it’s going to go too quickly. Toward the end, it’s incredibly harsh. There were times I could barely stomach it because you’re smoking in such a way that it is just destroying your palate. 

The game is enjoyable. The camaraderie is enjoyable. Winning is undoubtedly enjoyable, but there’s nothing pleasant about the smoke when trying to win.

Branching into the U.S. Market

Cigar Life Guy: Principle Cigars has been around for ten years. What can the world expect from it in the future?

Darren Cioffi: You can expect more of the same. We have a year of more releases than we did last year. You can expect the strengthening of some of our partnerships. We’re going to be doing more with Carillo in the coming years. We’re excited about some new partners we have yet to make public. I expect growth, not only in new markets, but we are starting to pay more attention to the homefront. We have taken a passive approach to the United States because our focus has been overseas, but in the coming years, you’ll see a lot more in the States for us.

Cigar Life Guy: Have we missed anything? Please tell us anything else you’d like the cigar world to know.

Darren Cioffi: Check us out for yourself. I’m accessible. I love when people tell me what they like, and I can suggest a cigar for them. I love to talk to people who can articulate what they enjoy and don’t enjoy about cigars and open their eyes to new things that may fit into what they’re looking for. I’m here. I hope to see more of you in the coming year.

Check out the latest from Principle Cigars here and Follow Darren and Principle Cigars on Instagram.

Photo credit: Principle Cigars