Smoke Rings: An Interview With Robert Caldwell

On today's episode of Smoke Rings, I'm joined by a very special guest: Mr. Robert Caldwell of Caldwell Cigars. Tune in as Robert and I discuss his introduction to cigars, the history of the Caldwell brand, and the inspiration behind Caldwell's core King is Dead and Long Live the King blends. This is the first installment in a two-part interview with Robert, so be sure to keep an eye out for the second half in coming weeks.

Note: The following transcription has been edited for clarity and brevity.

[Shane Ireland]: Welcome, Robert! First of all, thank you for joining us today. So for our customers and our viewers out there who may not know your full story, should we take it from the top? How'd you get into the tobacco industry? How'd you get into cigars?

[Robert Caldwell]: I started smoking cigars at a pretty young age — I'm not gonna mention how old I was — and I started smoking just like how anybody smokes. It was all machine-made stuff. But one day, my brother-in-law, who was a cigar smoker himself, caught me smoking. My mom was out of town, and he was house sitting with my sister. He immediately took me down to the Ernesto Perez Carrillo Factory in Little Havana, Miami and bought me an A-size Maduro El Cuarito with the purpose of trying to make me sick so I would never smoke again.

So I got the cigar, and though it was too much cigar for me, I smoked a third of it. The next day, I smoked another third. And then, I just fell in love. When we were at Carrillo's Factory, I was very much enamored by the whole process and atmosphere. My brother-in-law also brought me to a retailer that was close to my house once to grab some cigars. So I rode my bike down to that retailer and I said, "My brother-in-law, Peter, sent me. Here's 20 bucks. He wants cigars." So the guy started selling me cigars, even though he shouldn't have. But I just fell in love at an early age.

So throughout my life, I've always smoked cigars. And I kept hearing people tell me, "Hey, you like cigars so much, you should get in the industry," but I just shrugged it off. But then, one night, I went out for my birthday. After valeting my car and sitting down at the restaurant, I realized I'd left my cigars in the car, so I asked the staff, "Do you have a cigars?", and they did. They had a huge walk-in, double-door humidor. I'll be honest, the cigars weren't great: They were cracked, they were dried out — just trash selection. But I grabbed one and had an okay experience. I visited this place all the time, and was sort of shocked by the poor selection and quality of their stock. So when I got back home, I went online and searched for cigar services companies in Miami, looking for someone who could provide cigars to restaurants and hotels. And nothing existed.

[SI]: Which is kind of hard to believe. Yeah.

Robert Caldwell at Low Country Pipe & Cigar

[RC]: Yeah, exactly. It was really crazy, actually, because this was like 15 years ago, and Miami's a huge destination for cigar smokers. Plus when you're on vacation, particularly in South Florida, you wanna smoke and it's Miami. So then, the next day I go to dinner with one of my now business partners. I light a cigar, and the restaurant manager comes out and says, "Oh, that smells really good. Let me bring an ashtray." As the night progressed, he continued to comment about my cigar, so eventually I said, "Oh, I have a company and we distribute cigars to restaurants and hotels." I tell him that we rate the menu, we train the staff, we provide the humidor, etc. And all of this, you know, is just selling air, but the guy bites. He says, "Well, we have 11 restaurants. Can you set us up on Monday?"

So Monday morning, bright and shiny, I drove to a retailer in Bal Harbor, Florida — Mike's Cigars — and I bought 11 countertop display humidors. I bought Romeo y Julieta, Macanudo, and all the other brands you would buy to stock 'em with. At the time, I had a retailer friend, George, who worked on a counter in Miami and was unhappy with his work situation. He was looking for another job. So I went to set up these accounts, and I called George and said, "We're in business. We're doing restaurant and hotel cigar sales. We've got 11 restaurants already." So he says, "Great." So George comes on for about three weeks as a partner.

Originally, I was supposed to provide the money, and he was gonna be the sweat guy. But after a couple weeks, he said, "Listen, I need a salary. I'm not in a position to work for equity. So, I'm leaving." I said, "Alright, fine. I'll keep the company." I mean, at that point, it was nothing. Over the coming months, I started working nights and weekends, just soliciting accounts, and we got to the point where we had about 150 high-end hotels and restaurants in the Miami area. Then, Michael Mina, a highly acclaimed chef out of San Francisco who owns Bourbon Steak, reached out to me. We were selling cigars to one of his restaurants, and he wanted to come and make his own cigar.

[SI]: Oh, wow.

[RC]: Yeah. So we ended up working with Camacho. We flew down to Camacho, and we took a Camacho Liberty and modified it. We did 200 boxes of Michael Mina exclusive Liberties. That was my first toe in the water creating cigars. But I kept getting requests for more expensive cigars. This was 15 years ago. At that point, Davidoff didn't have Royals, and none of the other stuff was out there yet. So I decided I had to build a brand. I worked with Camacho and I got what were, I think, old Liberties and old Anniversary, etc. I did my own labels and then stocked them in the hotels at a higher price than anything else. And that worked really well.

Eventually, I started working on my own blends for the hotels. The distribution company that started as a kind of "at night and on weekends" thing turned into a full-time gig. The manufacturing just fell into that as we continued to see a need for higher-end or more exotic cigars for the accounts. It also led to really good friendships with other cigar makers, including Christian Eiroa, who at the time had sold Camacho and was returning to CLE and Asylum.

Robert Caldwell at Low Country Pipe & Cigars | Caldwell Cigars at

At the time, I was renting a warehouse in Miami in an area called Wynwood. Wynwood is now a really cool, very trendy arts district, but at the time, it was the cheapest rent you could find in Miami. One day, Christian came by the warehouse and then a bunch of magical things happened: Louis Vuitton came into the Miami Design District and bought up all the real estate there. A sister neighborhood to Wynwood, the Design District had previously been a manufacturing area for furniture, but at the time, it was the area for a bustling creative industry with photography, art gallery, and stuff like that. But after Louis Vuitton came in, they all got bumped out and pushed over into Wynwood very quickly. After this news broke, Christian called me and suggested we set up a factory at my space. I thought it was a cool idea, so we converted the warehouse and ended up building a cigar factory in Miami, launching a brand called "Wynwood Cigar Factory." And it was incredibly successful out of the gates. Within 60 or 90 days, we were producing 25,000 Miami-made cigars and selling them all at a very premium price for the time.

Christian and I had a really successful, very beautiful, and cool brand, but we just didn't get along as business partners. So I walked and then Christian just focused on CLE and Asylum. That's when I went back to the drawing board and came up with Caldwell. So the brand's history is completely spotty and entirely accidental. When I got into the industry, I had zero desire to be a cigar manufacturer. In fact, when I was running the hotel company, a cigar brand that I was working with approached me and said, "Hey, we want to relaunch and rebuild the brand around you. The brand is this entertainment hospitality thing that you're doing." And I said, "No, I will never be the face of a cigar company." So, it was really serendipitous, I guess, because I ended up doing what I love, but it was entirely accidental. And even today it's like I'm in denial. I still don't really like the front side of it. I like manufacturing, I like selling, I like creating, but actually being the face of the brand is the hard part.

The easy part is creating brands, creating blends, etc. The hard part is going out there and just being the face of the brand all the time. Like yesterday, I had a layover in Charlotte, and I'm walking through the airport and I see a guy and he nods to me. And so I nod back. And I keep walking, and I see another guy, and he nods to me. It's weird, you know. Like you're out in public and consumers know who you are. If you're a cigar smoker, and especially within my community of smokers, I'm an identifiable person to this niche of people. But it's really strange, because sometimes people will come and approach me and it's very flattering, but I just sometimes I jsut want to hide in the shadows.

[SI]: It's surreal. Because, you know, premium tobacco is a niche within a niche. You know what I mean? And the more that you get into the boutique side of cigars or into pipes, the more niche it gets. But it's nice to see cigar smokers or pipe smokers out in the wild. 10 years ago, if I saw a pipe smoker out in the world, it felt like that was a unicorn, you know? But I think there's been a renaissance in premium cigars and pipes over the last 10 years.

I think the interesting part about your story for me, Robert, is how your company progressed. Usually manufacturing begets the distribution side of it, so it's interesting to me that you kind of worked in the backwards direction there. So, getting back to the Caldwell brand specifically. When did that launch? What were the first products?

[RC]: 2013, I suppose. It might have been '14. I'm really bad with dates, but I'm pretty sure it was '13. And we launched with the King Is Dead, Long Live The King, and Eastern Standard.

[SI]: All at the same time?

Caldwell Cigars at

[RC]: Yeah. It was supposed to be just the King Is Dead and Long Live The King. Eastern Standard wasn't part of the original brand concept, but then I had the perfect blend and a really cool concept for artwork. Everything just sort of added up, so we ended up launching all three. That said, the King Is Dead and Long Live The King were the two that worked as a brand. Eastern Standard was kind of like this third wheel — the branding just didn't go along with the others perfectly. So then after that, we launched Last Czar, which played into the royalty concept or theme, but also linked back to the Eastern Standard, because I felt like the portfolio was discombobulated.

[SI]: Sure, sure, sure. So, what about the concept behind the branding for Long Live The King and the King Is Dead? Where did that come from?

[RC]: So King Is Dead was a blend that I was working on for like five or six years before we started Caldwell. So it was a tobacco called Negrito, a very special tobacco. It didn't burn well and it didn't blend. If you blended it, it burned but didn't taste good. If you put any in the filler, then it wouldn't burn and it tasted weird. So it took a very long time to build a blend — like five to seven years — that tasted amazing. But we did just that and we were very proud of ourselves.

There was another blend that I'd always had from the Wynwood Cigar Factory that I ported over to Caldwell, and that became Long Live The King. While I was blending the two, I was smoking these cigar consecutively, and I noticed that they worked really well together. So I modified the blends a little tiny bit to make them completely harmonious from one cigar to the next, and it just created this amazing experience. So the branding became "King Is Dead. Long Live The King." As soon as the current king dies, the next king reigns... That was kind of the concept behind the artwork of the brands.

When I went out to sell it to retailers, I remember walking into a store in California and pitching the concept. They were like, "Wait a minute, so this cigar does not taste good unless I smoke this other cigar before it?" And of course, I say, "No. They both taste really, really good separately. It's just if you follow this pathway from one blend into the next, it creates a more unique experience." They said that they couldn't sell them and, "I don't want your cigars."

So, when I walked into the next store, I just said, "King Is Dead. Long Live The King," and I just kept my mouth shut. "These are great. I'll take them." In fact, the only "no" that we had on that sales trip was the first retailer, so we just dropped the whole pitch going forward and every single retailer for the week ended up buying our product. That was kind of a learning curve for us, but the original approach of the brand was, if you sit down to smoke two cigars, smoke these two. If not, smoke one of the two.

[SI]: The narrative was hard for them to wrap their heads around. You know, it's interesting that you say that California bit, because my first exposure to Caldwell was in a shop called Liberty Tobacco in San Diego. And I have to say, it was the artwork that caught my attention immediately, and I think that's one thing about your brands that's really distinctive and sort of important, too. So, I saw the artwork and bought a couple cigars in the vitolas that were in my size range. And I was hooked after that.

But yeah, I think, I think that's one thing that consumers have recognized over the years from your brand is the artwork behind it, too. So real quick, I wanna touch more on the tobacco nerd side of this. The Negrito, you said that it was a difficult component to work with. Why were you so determined to make it work? Like, what was so special about it that you had to go through like the years-long process of nailing it?

[RC]: So, when I started making cigars for the hotels, I had a brand that I made with a manufacturer named Fufu Reyes or Augusto Reyes, who had a brand called "Nativo". That is just such a special cigar. So I went to work with him to create a brand. Currently, he is kind of disconnected from premier cigar manufacturing; he has a brand called "Saga" that his daughter runs, but at the time he had this brand that was seriously special. And so, I went to meet him and we started building this little brand that I sold in the hotels. And his brother Leo Reyes is a huge tobacco grower in the Dominican Republic; he has one of the largest seed banks there, if not the largest. So he's always growing test crops and those kinds of things.

And so one time during a visit to Augusto's factory, he handed me what's called a "Pachuche," which is just a little strip of filler wrapped up into binder leaf, or wrapper leaf that you smoke in pure form to experience the flavor. And as I puffed it, all of a sudden a light just went off. It was so unique and so good. Like I said, it didn't burn well, so I spent the entire day just relighting this thing. But it was so special. And it struck a chord with me that I had to make a cigar that tasted like that.

Like I said, it took forever to do it because you couldn't get it to burn or you couldn't get to blend. And now, there's two other manufacturers that have Negrito wrapper, but no one uses it in the filler except us. So we're the only ones still to this day that use Negrito as one of the filler components. But yeah, it was just one of those things that to me was like an equation that I had to figure out and solve because I wanted to produce a cigar that tasted that way.

To be continued...

Caldwell Cigars at


Start a conversation:

This will not be shared with anyone

challenge image
Enter the circled word below: