Smoke Rings: An Interview With Robert Caldwell Pt.2

Welcome back to Smoke Rings. On today's episode, I continue my interview with the founder of Caldwell and Lost & Found cigars, Robert Caldwell. Tune in as Robert and I discuss a few exciting and upcoming Caldwell projects, some of his favorite cigars from the past, tips for smoking slowly, and a deep dive into the pros and cons of cellophane packaging. If you missed the previous installment, be sure to check out the first part of this interview, and don't forget to explore Caldwell's full selection of premium cigars over on the site.

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

[Shane Ireland]: So, over the years, what other components or special leaves have got you excited? Is there anything coming down the pipeline now that's perhaps on the rare or special side?

[Robert Caldwell]: Yeah, there are a bunch of things, but the one that first comes to mind was when I went to work with Carrillo years ago. When we started Caldwell, we had the premium cigars — King is Dead, Long Live The King, and Eastern Standard — and then we had three other brands that were called Sevillana, Murcias, and Gibraltar, which went for around $4.5 to $6 retail. Like you could get a 6" x 60 for six bucks, or for $4.5 you could get the Corona Gorda. But the prices were so low that guys were scared of them, and they didn't sell well. When our production took off in a crazy way with Caldwell at the factory, we couldn't produce the Sevillana, Murcias, and Gibraltar brands because we just didn't have room for them in our tiny building.

Caldwell Cigar Company: Anastasia Vintage 2016 LE Corona Clasica Cigars

So Carrillo came up to me at a multi-vendor event and was just kind of like looking at the packaging for these cigars. We immediately hit it off by talking about Spain; my wife's Spanish, and Carrillo is obsessed with Spain. So we had this great conversation, and he invites me to the Carrillo factory to work on porting my more inexpensive cigars over to his production. I get to the factory, and the samples are really good. But as he's walking me around this beautiful little factory, he says, 'I really want you to try this tobacco.' So we go up and he takes a cigar and puts the wrapper right on top of some Connecticut, and says 'smoke it.' And I'm just like, 'what is this?' But that's the wrapper that turned into Anastasia. He had only a very small amount, but he created a blend, sent me the prototype, and I was blown away: It was a home run. We ended up spending about six months blending until I just said, 'No, no. It was the first one.'

[S.I.]: It was the first try. Yeah.

[R.C.]: So on the first swing we hit that blend, and that was another instance where it came down to a very special wrapper. It was like seven or eight or nine years old at the time, and had gone through an extra fermentation process. It was very unique. It tasted nothing like the tobacco family in which it lives. It was just a really beautiful concept. So that was another example of a cigar that I was really proud to release because it was just such a special blend.

Actually, we have the next Anastasia coming soon; there's a new release. We did a very small, limited project, but we have a proper, four-SKU release coming this summer. And I think it'll strike the same chord with consumers that Anastasia struck with me.

[S.I.]: That's fantastic. I can't wait for that. So circling back to the artwork and packaging aspect for a moment. Presentation seems really important to the Caldwell brand. Can you speak to that a bit?

[R.C.]: Yeah, I mean, presentation is the first step; people buy with their eyes. If you walk down the street, and you see somebody that's attractive to you, you're attracted to them at that moment. You don't know if they're intelligent, or if they're fun to hang out with; you don't know anything about them. The same goes for cigars. If you have a cigar that's so much better than its packaging leads you to believe, that's great. But people still have to take a chance and discover that cigar. Alternatively, if you have a great cigar with great packaging, more people are going to reach for that cigar. So that's always been our approach. We want to produce great cigars with great packaging that draws attention.

But with Anastasia, when we launched the brand with the green label, not everybody got it. So a lot of people thought the cigar was too light or that the sizes were small. We were using the 47 x 7" format for our Churchill, and a 49 x 5" for the Robusto, another 43 x 5". We had really gourmet sizes, but the market was all about the 6" x 50 power Nicaraguan. It wasn't until the brand transitioned to the blue label and the blue label died because we ran out of tobacco, for the Anastasia to really take off. Now there's like a hysteria behind Anastasia — we get about 20 calls a week asking for Anastasia — but it took the market pivoting in our direction, I think, for consumers and retailers to appreciate it for what it was.

[S.I.]: And speaking of the market, I think you guys were a little bit ahead of the curve on that. A lot of guys out there are realizing that some of these more esoteric or more old-school sizes can give them a totally different appreciation of the cigar, especially of the wrapper leaf. You know what I mean? You're not gonna get the same experience from a great wrapper with a 7" x 70 format, you know? The ratio of binder to filler to wrapper has to be in that sweet spot. And, for me, that just happens a lot when you're talking about Coronas and sub-52 ring gauges. So Anastasia, obviously, was big, and a lot of guys are calling and asking for it still. But what would you say is the most popular Caldwell cigar overall?

[R.C.]: Blind Man's Bluff.

[S.I.]: Really? Yeah. That's a great smoke.

[R.C.]: Good cigars. Very good price point.

[S.I.]: Yeah. And what was the Limited Edition for last year?

[R.C.]: This is Trouble.

[S.I.]: This is Trouble. Yeah. Fantastic. So what was special about that one?

[R.C.]: Well, it's an entirely different blend. So it was a Maduro, so it fit in our Maduro collection. Blind Man's Bluff is a very good cigar for a very good value, so we wanted to produce a one-time, limited-edition version of that cigar that still spoke to the same smoker in terms of what they looked for in a cigar, but then blow it out of the water — pull out all the stops, cost is no option. Blind Man's Bluff are great cigars at everyday price points, whereas the Caldwell Collection comprises more premium price points and everyday cigars for some, but not for all. So to apply that same concept, we went back to the drawing board and rebuilt Blind Man's Bluff Maduro with different components as a special occasion cigar, but with the same conceptual smoker in mind.

[S.I.]: Got it. So circling back to limited leaf and smaller production runs. I know the term 'boutique' gets thrown around a lot, but for the sake of the argument, being a boutique manufacturer surely affords you the flexibility and agility to run with some of these special projects, right? So what are you looking for next? What irons do you have in the fire right now?

Robert Caldwell of Caldwell Cigars Company

[R.C.]: So we have a couple of brand extensions coming this summer. And then we have a project called Crafted and Curated, which is really cool. You're smoking one right now, I'm smoking one. So the concept there is: if there are no limitations on anything, what would you do? So just now, I was smoking a 30 x 5.75". That's not a size that sells, but it's really good, so I'm gonna produce it anyways. But I'm going to produce 200 boxes instead of 20,000, you know, because it's just me having fun. No one's watching. I'm making cigars for myself, cigars that I find interesting, but then sharing those with the customers

[S.I.]: That's really cool.

[R.C.]: That's effectively the concept. Some of them, of course, will be focused on showcasing smaller amounts of tobacco available, or the tobacco has been very aged, or the sizes are funky. I have one called Louie the Last. It's a Last Czar. So it's made using slightly different components, a different priming for the wrapper, and it's coming out in a 42 x 5.25" size.

[S.I.]: Mm. That sounds perfect.

[R.C.]: Yeah. And it's awesome. And we're doing 500 boxes. Take it or leave it. If you don't want it, don't smoke it. These are cigars that I'd almost rather people not buy, because I will smoke them. Because it's what I roll for myself anyways.

[S.I.]: It has to be liberating to be at that point with the brand where you can really have some fun and play with more esoteric sizes and components. I'm speaking for myself here, but honestly I think a lot of smokers out there feel the same way. That's what the market wants right now — at least the premium side of the market. We want to see the absolute best products that we can get, and price doesn't matter quite as much. And being able to go back to it for years and years and years and have the blend be consistent doesn't matter quite as much as having a special experience. I think that is the main thing. And that's something that I really appreciate about what you guys are doing with the Lost and Found brand. I also think there's like an educational piece to this. When I first started getting into tobacco and cigars, not a lot of manufacturers were super transparent about the components they were using. There wasn't a ton of information out there except for really basic stuff like, this is a Connecticut wrapper, or this is a Maduro wrapper. You didn't really know the nitty gritty about what all goes into production and what makes something special. And I think that's something that you guys have been at the forefront of. That transparency gives the consumer an opportunity to not only try a bunch of different stuff, but know what they're trying in most cases.

Of course, there are certain things you have to keep close to the chest, like the Anastasia blend. And I think Savages is another one that doesn't disclose all the components. But by and large, it's nice to give consumers the information to form a starting point that they can branch off from. With that information, you can recognize the little tweaks and know the difference between the blends; it allows you to really sort of drill down on your tastes as a consumer. Interesting. So anything else in the wings?

[R.C.]: Well, I can't tell you everything, but I'll leak something. So we had the Escape Plan, which was a box-pressed King is Dead, and we're going to keep that as a sub-brand concept. So we're gonna have an Escape Plan Eastern Standard and an Escape Plan Long Live the King.

[S.I.]: All box-pressed?

[R.C.]: All box-pressed. No cellophane. I don't think cigars should be sold with cellophane, but sometimes you have to. But something like Escape Plan, you can get away with. So we have those coming, and we have some additional fun twists coming out this summer.

[S.I.]: Let me poke on the cellophane concept for a little bit. So why do you say that in an ideal world, cellophane wouldn't be a thing?

[R.C.]: It's horrible. I mean, that's the long and short of it. Think about wine. When you drink wine, you decant the wine first, right? The wine needs to breathe. A cigar, which is typically around 90 or 120 day-old coming from the factory. That is a very generous amount of time to apply to most cigars. But even at 120 days, that cigar is not done developing.

[S.I.]: It's not done coming together,

[R.C.]: And so when you put in cellophane, it just kind of shocks it. And then when you take it outta the cellophane and smoke it right away, it has a different essence than if it's not in cellophane. So a cigar that has been stored with cellophane versus a cigar stored without cellophane tastes very different.

[S.I.]: Right. And I have to imagine that when you're working as a blender, you're not smoking stuff coming out of cellophane either. You're smoking bundles or stuff that's in a dry room and stuff.

[R.C.]: And I won't. I will very rarely take a cigar out of cellophane and put it in my mouth. If I'm checking inbound products to make sure everything's smoking correctly and that type of thing, sure. But when I'm at home, at 8:30 at night sitting outside smoking a cigar, I have special humidors. Even with regular Caldwell production, they go in my special humidor and they age with no cellophane. And the dynamic of the cigar is different. It's a different cigar. And so for certain projects we will have no cellophane. But the cellophane does protect the cigar in transport, so it will always be a part of our process.

[S.I.]: So, then, is it safe to assume that if you're putting stuff down for long-term aging, cellophane may be arresting the development of the blend, but also protecting it long term? Or is it literally just about protecting the cigar in transit?

[R.C.]: Yeah, it's a physical thing. It helps protect the cigar with people touching them, or them bouncing around in the box. But, I mean, I see terminology bouncing around on platforms like 'this has been box aged.' What does that mean? It means it's been sitting in a box and nobody has bought it for years. And that's cool, but if you had that same cigar with no cellophane on it, that wasn't box aged, but was put in a humidor or left in an aging room, it's gonna taste 25 times better.

[S.I.]: Ah, okay. Yeah, I would agree with that largely, too. I've done a little bit of both. I've pulled stuff out of the cellophane and put it in my humidor. I've also left stuff in cellophane in a bag with a Boveda. And I've definitely had some good experiences with something that was pulled out of its cellophane after like 10 years. But by and large, I think you're right. The stuff that's not cellophane wrapped tends to age more dramatically in the short term; and it probably has longer legs and will be a little bit smoother and more well rounded in the long term. Either way, I find that very interesting, because it's not a topic that gets tossed around a lot these days.

Caldwell Cigars at

[R.C.]: No. And the thing is: I think that 99% of manufacturers would sell cigars with no cellophane if they could. But the problem is that 50-60% of retailers won't sell your cigars without cellophane, cause they want barcodes or UPC information. There's also the whole sanitation aspect: you know, these cigars are going in your mouth, so we don't want people to touch them. But we don't photograph cigars with cellophane on them, because they don't look as pretty. But then the concern of retailers is what drives us to use cellophane.

When we first started, we had no cello, then we transitioned to half cello; if you wanted cello, you had to request it. But then we went all cellophane and our sales took off because we were able to deal with companies that wouldn't deal with us previously. But now I've got a retailer that harasses me all the time about the King is Dead Escape Plan. He tells me that I have to cellophane these cigars, and I'm like, don't buy them. I don't care if you buy them or not. I'm not cellophaning that cigar.

[S.I.]: Right. If that's the vision you have for the product and that's the way that you want it to taste, then that's the way it is. Interesting. Let me ask you, going back to the early days, I'm curious, what were some of your favorite smokes or some of the premium cigars that you smoked before you were manufacturing your own?

[R.C.]: So it sort of came in stages. So the first stage, which was nearly 20 years ago, was the Punch Rare Corojo. That cigar was so good and it was a very good price. It was like $5 Rubosto or something at the time. So that was a cigar that just kind of did something for me in that sense. Later on, I was down in the Keys with my brother-in-law and we wanted a cigar. I didn't have any cigars on me, so we drove over to a nearby retailer and they had a pile of Davidoff Special B, which was like a Corona with a little Torpedo tip. And they were selling them for like a hundred bucks a box. These cigars retail normally for like 350 a box, but they were just blowing 'em out. They had old packaging and were really old already. I asked them how many they had, and my brother-in-law and I ended up buying them all. I had never smoked it, but I knew it was worth the price. And they were amazing.

It was a cigar that I just nursed. I just, I remember when I smoked my last one, it felt like a tragedy. I smoked half the boxes myself, and my brother-in-law got the other half. It was a very special thing. And then I had a similar experience with the Davidoff Millennium blend, a petite Corona and a Lancero, I think. Then Carrillo has a cigar called EPC, I guess it was called Artesanos de Miami. It was like the last cigar made in little Havana by Carrillo. They're really good now. I think they might have peaked a couple years ago, but I discovered that cigar maybe three years post-production, and it just blew my mind.

[S.I.]: Interesting. So it also sounds like your personal preference leans more towards the smaller ring gauge stuff too.

[R.C.]: Oh yeah.

[S.I.]: Why is that?

[R.C.]: You get better flavor. Like if you're a scotch drinker, do you drink your scotch neat or do you drink it with water? I feel like a larger ring gauge is gonna be kind of a watered down version. Of course, that has its place too, but you kind of want to try it as close to its purest form. So to me, a 40 to 46 ring gauge is perfection. Length wise, seven inches is enjoyable, but something between five and six and a half inches, and between a 40 and 46 ring gauge, is the sweet spot, I think — the pure pleasure point of a cigar. If you get a little longer, it's as enjoyable, but it's a different experience.

Like a 7" x 47 is different, it changes it a little bit. I think you want it to be just a little shorter, but then again, back to the consumer, it's a value proposition, too. I'm gonna give you that cigar for $13 retail, and you can get the Robusto for $14 or whatever. The most expensive part of a cigar is the wrapper. So you're gonna be very close in price point between a Corona and a Robusto. But I don't think that a lot of consumers understand well enough that this is what you wanna smoke.

[S.I.]: Right. I've been saying this for a long time too. Some of this is personal preference, but I would rather smoke two small cigars in a row or two smaller pipes in a row than one giant bowl of tobacco or one super big cigar. I don't know why I've just always been that way.

[R.C.]: And, in addition to that, when I smoke a 46 x 6" Corona, it'll take me almost two hours. I smoke slowly, and a cigar should be smoked pretty slowly. A lot of people smoke a lot faster. I'll occasionally smoke faster, if I'm at an event or something. If I'm talking and having to keep the cigar lit, I can smoke a Corona in 45 minutes. But if I'm sitting in my house, I'll sit down and smoke a Corona, and it's an hour-and-a-half, two-hour cigar. So I think people need to learn to smoke a little more slowly, and if they do the value proposition increases because you get two hours for the same price. It's worth it.

[S.I.]: We were talking about that on the pipe side earlier, too. Just the slower you can go, the better the flavor. And I think that's just true for tobacco in general. Well Robert, thank you so much for sitting down with me today.

[R.C.]: My pleasure

[S.I.]: We'll have to do this again sometime soon. I'll think of some more nerdy questions and we'll get in the weeds again.

[R.C.]: Absolutely. Sounds good

[S.I.]: Thanks everybody for watching. Thank you for coming, Robert. And we'll see you next time.

Caldwell Cigars at


Start a conversation:

This will not be shared with anyone

challenge image
Enter the circled word below: