Interview: Robert Caldwell & Jeremy McDonald of Caldwell Cigar Co.

Caldwell Cigar Company
Joshua Child
Written by Joshua Child

From his colorful start to his current role as owner of his own cigar company, Robert Caldwell has a long history with tobacco but most smokers will know him as the creator of Wynwood Cigars. The idea behind Wynwood was a simple one: fresh-rolled cigars with an eye towards artistic presentation. Having smoked cigars right off the rolling tables on our recent trip to Nicaragua I can safely say there is a noticeable bump in flavor, strength and intensity when compared to the cigars on the shelves. Wynwood allowed smokers to […]


From his colorful start to his current role as owner of his own cigar company, Robert Caldwell has a long history with tobacco but most smokers will know him as the creator of Wynwood Cigars. The idea behind Wynwood was a simple one: fresh-rolled cigars with an eye towards artistic presentation. Having smoked cigars right off the rolling tables on our recent trip to Nicaragua I can safely say there is a noticeable bump in flavor, strength and intensity when compared to the cigars on the shelves. Wynwood allowed smokers to experience this phenomenon by rolling the cigars in Miami and shipping them to retailers almost immediately after packaging. Others have followed in his footsteps with projects like the Paul Stulac  No Dress Code.

Sadly, Wynwood was not to last as Caldwell and Christian Eiroa of CLE Cigars broke ties last year and the Wynwood factory in Miami was closed. However, things are looking up for Caldwell as he’s set to debut 3 cigars with his new company in less than a month. With this latest venture he’s done a 180° turn, finding the rarest and oldest tobacco he can lay his hands on. Caldwell is locked & loaded.

robert caldwell baseball 1       robert caldwell baseball 2


CM: Take us through your discovery of cigars to where you are today?

Caldwell: I started smoking cigars when I was 10. Mainly cheap machine made cigars I could 5-finger from gas stations. I was caught smoking by my brother-in-law when I was 12. In an attempt to dissuade me from smoking, he gave me a La Gloria Maduro. I immediately fell in love.

As for the business, I got into manufacturing about 7 years ago. I ended up making a brand which was sold exclusively to high end hotels and restaurants. I found that it was very hard to find a good cigar in the hotels around Miami so I built a brand to showcase in these venues. It was a limited project. We featured rare tobaccos and very well aged cigars. I worked with several manufacturers through this process. From there, I decided that I wanted to build a factory in Wynwood, which is the arts district in Miami. Everyone thought I was crazy. I thought this area was a fantastic place to showcase the artistry of cigar manufacturing. From there the Wynwood brand was born. I always wanted to share with people the experience of a fresh-rolled cigars. To me, they were the best kept secret in the industry. I worked mainly with Honduran Corojo tobacco for this project, as the sweetness of this leaf overcomes most of the bitterness that you find when smoking fresh tobacco. Unfortunately, I had to leave this project due to differences with my former partner. I am very stubborn when it comes to business. I only want to make the highest quality cigars I can. Sadly, that factory closed just a few weeks after I left.

CM: An essential element to the Wynwood project was presentation. How important is presentation, artistry and aesthetic appeal when it comes to your brands and why do feel it is so critical?

Caldwell: That’s the million dollar question. I think packaging plays a huge part. I like to think of packaging more as presentation. As a manufacturer you want people attracted to your product. You want them to be curious. A retailer wants the same but also he wants the packaging to sell the product. I develop my boxes to tell a story. Art does that. It reminds you of the artisan nature of the product. I like blending cards. I want the customer to have their questions answered. They can look at the box and know what the cigar is made out of. The more educated the consumers are, the better off the industry is. Cigars are a luxury product. Luxury is in the details. I also like simplicity. Packaging should tell the story of the owner and a statement about the company.

The Caldwell Collection from left to right: Eastern Standard, Long Live the King and The King Is Dead.

The Caldwell Collection from left to right: Eastern Standard, Long Live the King and The King Is Dead.

CM: I think it is an interesting choice to place blend cards in all of your boxes. I’ve noticed that much of the industry is afraid to share information on their cigars. Why do you think manufacturers are reluctant to pull back the “veil” on their blends?

Caldwell: I can tell you where my tobacco comes from, the varietal, what vintage, who grows it and you will never be able to replicate my blend. You might get 70% similar taste, but you would have to know what primings etc. It’s doable but very difficult. That being said, manufacturers are scared to share because of this fear, or more likely, they enjoy the mysticism of not doing so.

CM: Let’s get to your latest venture. Caldwell Cigar Co. You have covered some of this in your press-release back in February but how soon after Wynwood dissolved did you know this was the direction you were going in? Creating your own company with your own name is a fairly big step. Once you made the decision, did you know which growing regions or factories to utilize?

Caldwell: I had a couple of people approach me to do joint ventures or license deals almost immediately but the two bigger companies that approached me both said the same thing: I would be selling myself short if I didn’t go at it solo. I came down to the Dominican Republic and I met with Henderson & William Ventura within a week of leaving Wynwood. William was with Davidoff for 20+ years managing production, overseeing quality control etc. I have known them for years. Their construction is flawless. I also met with Leo Reyes on that trip. Leo is one of the premier growers of tobacco in the world. He is almost weirdly romantic about the leaf and he shared with me some very rare, aged tobacco. It was on this trip that I decided to maybe go at it alone. When I got back to Miami I had a few people reach out to me who were still working for my ex-partner and they told me if I came back, they would be with me. I felt at this time that I had no other choice but to go at it alone.

The name of the company is actually Down and Back. We are doing our cigar business as Caldwell Cigar Co. We are made up of myself and one of my best friends, Hernando Caicedo, as the two managing principals. All of our employees also have an equity stake in the company. I wanted to use my name because I feel if you take great pride in what you do, you should put your name on it.

The reason I chose the Dominican is because they were the first country to cultivate cigar tobacco. Cuba came 20 years after the Dominican. Cuba was too caught up in sugar to pay attention to tobacco. Also, the Dominican Republic grows a wider variety of tobacco than anywhere else. You have a very broad assortment of flavor here. Most other countries’ tobacco to me is “range bound”. We do use other leaf but our core is Dominican.

CM: In creating your debut blends did you have definite tobacco & flavor profiles in mind or was the blending process more free form?

Caldwell: I wanted to use Negrito. This became what is now The King Is Dead. I smoked the first year crop years ago and fell in love. It is very hard to blend with but it is such a unique flavor. From there I wanted something stronger. We developed Long Live The King using some very old Dominican Corojo crop. This leaf is special because it is next to impossible to find non-hybridized Corojo tobacco outside of Honduras. The last line, Eastern Standard (Dark Connecticut) is about the same body as The King Is Dead. This wrapper came to me by chance. The grower kept insisting I smoke it. I was hesitant to work with this leaf because it has a similar strength level as The King Is Dead but it was such an amazing cigar that I ran with it as well. So we developed all of the blends for a specific reason but were only planning to roll out two and ended up with three. My words to Leo (Leo Reyes Grower) when I sat down with him back in September were “I want the most unique and special tobaccos you have”

Caldwell Cigars All

From left to right: The King Is Dead, Long Live The King, Eastern Standard. Click on the photo to see them in full.

CM: How did you come up with the names for your blends? Do they have any meaning?

Caldwell: The naming concept for The King Is Dead / Long Live The King is basically: Smoke this. When you’re done, smoke that. The blends were developed for Long Live The King to follow one after the other. Smoking The King Is Dead first compliments the way Long Live The King smokes. Eastern Standard was just a hard as fuck name.

CM: When we spoke in person you talked a little bit about the Junior Varsity Collection. What details can you offer about these cigars?

Caldwell: Junior Varsity is a pretty simple concept. They’re really good cigars at a great price. Caldwell Collection uses all grade a tobaccos. The material used in Caldwell is very rare and very well aged. I know that for some people, Caldwell will not be an everyday smoke. We were mindful that there are a lot of people out there who cannot smoke a 10$ cigar everyday. The factory we are working with in the Dominican has cigars that they have been selling for years locally. They are fantastic smokes but never made it out of the country. When I was there, I would always smoke them and bring a few bundles back with me. These are the cigars we are using for the Junior Varsity Collection. We worked with the factory to tweak the blends a bit and to make sure we would bring in the sizes that make sense for the US market. We also did all of the design for them. The tobaccos used for these cigars are fantastic, well aged tobaccos. They are retailing from around 4.75$-6.90$.

Two of the cigars from the Junior Varsity Collection. On the left is the Gibraltar and on the right the Sevillana.

CM: Are all 3 of your debut cigars planned as annual releases or are you taking the Viaje route where everything is small batch one-time release with new blends every season?

Caldwell: No. What we are launching now are out staples. We will visit the limited edition thing later on but it will be a true limited. We have one addition coming to the portfolio this summer. Our growth plan will be to develop extensions to our current lines. All of the Caldwell Collection brands are stand alone brands at the moment. It isn’t one brand with three wrappers. We plan to add to each of the three lines after a couple years.

CM: It seems like every year a company must have 1-2 new products to join their existing portfolio. Do you feel this is a positive or negative thing for the industry?

Caldwell: I like the idea of doing yearly limiteds. There are some cigars that are amazing but the quantity that can be produced is too small to warrant a big production. It is an opportunity to showcase something special. I do not like when it is used as a marketing stunt.

CM: Tell us a little about the team you’ve built for Caldwell Cigar Co. and what their roles are.

Caldwell: The people that I brought in were the people that always believed in my approach to the industry. They are the people that really supported what I was doing last time around.

Jaclyn Sears will be doing sales and events. She is a really personable girl and loves tobacco. She worked with me doing marketing before and still brings these skills to the table. She is a natural when it comes to events and sales. She understands how to work an event and make customers feel welcome and involved.

Jeremy McDonald – Jeremy is a gourmet type of guy. He loves chocolate and coffee almost as much as I do. He connects really well with customers and is an inherent leader. He is our sales manager as well a stepping the line in a couple markets.

Wilson Vasquez – Wilson worked with me before in the mid-Atlantic. He is a natural sales person and knows a lot about tobacco. Wilson is the guy who always wants to learn more so that he can share it with other people. (Note: as of Fall 2014 Wilson Vasquez is no longer part of Caldwell Cigar Co.)

Danny Cordero – Danny is managing our office, customer service, shipments and inventory. He is the guy you never have to ask twice.

The Caldwell Cigar Co. team from left to right: Robert Caldwell, Wilson Vasquez, Henderson Ventura, Jeremy McDonald, Danny Cordero, Jaclyn Sears and Hernando Caicedo.

CM: Before you go, where do you see Caldwell Cigar Co. 5 years out?

Caldwell: I hope that in 5 years we are a strong brand doing things differently and having a blast.


From his employment at Maxamar Ultimate Cigars in Orange County, CA to working for Christian Eiroa (CLE Cigars, Wynwood, Asylum, One Shot One Kill, Hechicera, Pura Sol) as a West Coast Sales Rep, Jeremy Mcdonald is no stranger to the business. As the newly minted National Sales Manager for Caldwell Cigar Co. he may have his work cut out for him, but he’s right where he wants to be.

jeremy       jeremyback


CM: Tell us a little bit about yourself and your history in the industry.

Jeremy: Well when I was eighteen I started smoking cigars. I was in love at first sight. Every time I would go to a shop I would get something familiar and then pick out something new. I did this for years. I wanted to taste all the nuances there were in different cigars. I frequented a couple shops at this time. I asked at a few different shops if they needed help as I was looking for a second job to help with bills but no one was hiring. About six months later Ammar, the owner of Maxamar Ultimate Cigars, had a guy quit and he needed the store hours covered for the RTDA which is now the IPCPR (International Premium Cigar & Pipe Retailers Trade Show). So I jumped at it and took vacation time to work a week at Maxamar and well…I never left. I ended up quiting my other job to learn more of the operations side and ordering for the store. Then I became the store manager and ran it for another 6 years. I worked there all together for 11 years, taken under store owner Ammar’s wing and was taught the industry. I had done all I could do in the retail side and began looking for a job as a rep…hence Christian Eiroa.

CM: How did you and Robert meet?

Jeremy: I met Robert in Honduras right after I was hired with the company (CLE Cigars Christian Eiroa). I didn’t know him and actually when we met I thought he was a tool. He probably thought the same of me. He was wearing pink jeans and 1000 bracelets. I was thinking “Who is this guy?” Then I got to know him when we took Wynwood on the road and I began to really respect him as a tobacconist as well as consider him my friend. The dude has an amazing palate and we are constantly evaluating cigars. He is much harsher than I am when evaluating cigars.

CM: How difficult was the decision to leave the relatively established Eiroa for Caldwell Cigar Co.? What made the opportunity so special? Not just for you personally but for the industry?

Jeremy: As far as my decision to leave CLE it came down to this. We can remain comfortable in life or take risks. They are both respectable but have very different outcomes. I was comfortable with CLE. Robert is the wild card and that’s why I left. It was not a hard decision for me to make at all. I respect him as a person, I love his innovative ideas about marketing and packaging etc. and I love his style of blending. It’s all about complexity over strength. I believe in him and I believe in this company. All of us on this team are putting our blood and sweat into this. I am confident people will respond to it. That’s why it’s a risk for me, it was an easy decision to leave and come aboard Caldwell Cigar Co.

The lid pealed back on The King Is Dead. It looks like the blend card is on the front of the box.

CM: Considering how crowded the market is, how does “one more” boutique brand make a name for itself in the market?

Jeremy: Isn’t that the million dollar question? But seriously we are currently in an extremely over-saturated market with a lot of product that is the same old shit with the same profiles and the same packaging. With that said there’s some phenomenal boutique cigars out on the market right now that are being creative with blends and profiles. The way I look at it is simple. Look at the micro-brew explosion and what has happened there. There is a new micro-brew popping up every day and these guys are getting very innovative with barrel aging, using different ingredients and going for a different market altogether. They aren’t going for the Budweiser or Coors drinker. They are creating new beer drinkers. We are not going for the Macanudo smoker, we want to create new fans and I believe our product reflects what’s missing in this market.

I’m not saying we are the best cigar makers but I can say with confidence that we are bringing something new to the table using well aged/rare and specialty tobaccos. And our packaging…just look at it…sick! The cool thing is it’s not just our company thats on the rise, it’s the whole boutique market. We are a part of a changing industry right now and my hope is we can play a significant role in it.

CM: Being head of sales for a new cigar company what are your thoughts on some of the trends in the industry? For example there is an ever going trend to release “new, new, new”.

Jeremy: As far as the new releases happening too frequently, it does one thing, cannibalizes your core lines. You have to let your brand breathe and get its legs. We need to retrain the consumer that this is not MacDonald’s. Too many companies have released crap upon crap just because they need something new with no time put into it. No passion. No artistry. Honestly, it’s offensive to me. We have our core lines and we are going to build on them. Instead of new releases we will do limited runs of our core lines. This is more to keep relevant and keep the interest in the brand. It sucks but it’s a game that you almost have to play so that you don’t get forgotten. Thats what I hate about this MacDonald’s mentality this industry has gotten into.

CM: What makes the Caldwell Collection special to you?

Jeremy: I could answer this question with a lot of fluff due to the fact that we are using very well aged and rare tobaccos but the reality is simply this. Our blends stand out because they are different. When you smoke our cigar weather it’s for you or not, I can say this with confidence. Our cigars are unique and not run of the mill. I’m very proud of what Robert has created and our packaging, bands, and most importantly our cigars do stand on there own. We are not a gimmick. We are tobacco nerds through and through and we are damn proud of what we are doing. We are excited to be a part of this ever changing industry. Last words. Try our cigar, try another cigar and just keep smoking and challenging your palette with the wonderful blends that are our there.

About the author

Joshua Child

Joshua Child

Just an impostor in the cigar game who's only goal is to provide an unpretentious outlet for smokers. Other than cigars he enjoys people of substance, dogs, pugilism, and barrel aged spirits.