5 Cigars That Made My Career: Alan Rubin of Alec Bradley Cigars

Alan Rubin calls the time you get to enjoy a cigar, “the best hour of your day.” The founder of Alec Bradley Cigars knows what we know: “There’s a relaxation. You’re almost never alone when you have a cigar, you almost always have a friend with you. It’s that kind of meditative peace, and it makes, you know, we’ve always said that cigars break barriers and build bonds amongst people.”

Like you and me, Alan is a cigar guy. “If I wasn’t making them, I’d still be smoking. It’s still my hobby.” But he is making cigars, and tasty ones at that – and in this installment of 5 Cigars, we’re going to find out how it all began.

“It would have just been a business deal until the cigar gave us an opportunity to get to know one another.”

We all know the power of a cigar…its ability to connect us with others who share the passion. With Alan, it was evident when he was pitching a contract on behalf of his family’s hardware business: “The owner was in his 60s and he worked with his son, and I worked with my father at the time. And he called me into his office and I was prepared to give a presentation. And he said, ‘Son, do you smoke cigars?’ And I said, ‘I do.’ And he pulled out a cigar for each of us and we talked for three hours – talked about family, what it was like me working with my father, him working with his son. And ultimately, I got the contract. And you know, I’m gonna bet I was not the least expensive guy bidding, if that makes any sense…But we made a connection and he knew I’d be there for him…and it was all over that cigar.”

The Rise of Alec Bradley Cigars

A latecomer to the Boom, getting Alec Bradley cigars into the market was no easy ride. But with a string of high ratings to the company’s credit, their cigars have earned shelf space next to the classics. Emphasis, here, on “earned”: AB’s success is the result of hard work and taking chances (watch and you’ll see), and Alan Rubin & Co. have more than industry’s accolades to show for it – many of their marques have found their way into the humidors of millions.

“Everyone asked me, ‘How did you get in the cigar business?’ I said, ‘A series of consecutive bad decisions.’”

Along with those five cigars that got him here, Alan has some interesting stories any cigar lover can appreciate. So we sat down in comfortable leather chairs with something good to smoke (naturally) and talked about all of it, just to get it on the record. Today, we’ll tie together Rick James, Corona Gordas, Home Depot, Trojes tobacco, $5 cigars and Henke Kelner, along with Fine & Rare’s 10 tobacco blend and how he found out liquor stores open at 10am. Below, you’ll find a condensed version of why each of these cigars were pivotal to the building of Alec Bradley into a must-try brand. So spark up a smoke of your own, hit play and get a serious (but not too serious) taste of cigar history…Here’s what he had to say.

#1. Partagas

Alan: “ So first of all there were a couple of cigars before I ever got in the industry that really drew me to cigars. One was the cigar itself, and one was the experience of the cigar. So the first one was that my, one of my very close friends, my roommate in college, my roommates in college – their father was a very prominent businessman in South Florida of Cuban heritage…always had cigars on his desk. We’d go to his downtown office and see, you know, a beautiful humidor on his desk and I was always intrigued. One day he said to me ‘Alan, do you want a cigar?’ I was 22, and I said I’d love to try it and he gave me two cigars. He gave me a Cuban cigar and a Dominican cigar and he said ‘OK, this one you can smoke it anytime’ – and then the other one he said, you know, kind of a ‘don’t operate heavy equipment’ type of feel.”

“I was kind of just intrigued with the flavor that you were getting out of these leaves…I didn’t understand it, but I was intrigued.”

AR: “ So I smoked the first one and you know, it’s my first cigar. It was a Partagas Dominican that he gave me, and then a Cuban Partagas as well. So I was in my office, back then you could smoke in your offices…I was still a young guy and I smoked it, and I was kind of just intrigued with the flavor that you were getting out of these leaves. You know I didn’t understand it, but I was intrigued. And then I remember I waited a little bit of time, and a couple of weeks went by, and I was in my office on a Saturday doing some work and I said, ‘I’m gonna light up this other cigar.’ And I got a call on a Saturday to check some inventory. So I was smoking the cigar, sitting at my desk, and I got up and I had to climb up three rungs on a ladder to check some inventory – and I almost fell off the ladder. And I was like, ‘What is this?’ You know, I was a pretty novice cigar smoker, right? So I think back then it was just the difference, maybe the nicotine content back then, and it’s not like I was noticing big flavor differences – I didn’t really understand that part – but I definitely got a little head buzz off of it.”

One of the oldest cigar brands in the world, the Cuban Partagas has a bit of a spicy reputation – coupled with strong and intense flavor. The non-Cuban Partagas is an old-school classic made in the Dominican Republic; a mix of Dominican and Mexican San Andres tobaccos under a delicate Cameroon wrapper lends to a more medium-bodied experience that smacks of wood, cedar and earth. They may share the name, but many smokers who have tasted both – especially the Cuban Partagas D4 – will tell you they’re miles apart in taste.

#2. Occidental Reserve

Alan: “I started, and for sure struggled. You know, as we all have – everyone in the cigar business, when you’re first getting started. And then what happened was, I met a guy who’s still my executive vice president today – Ralph Montero. And Ralph had been in the business since he was 18. He was struggling, and I was struggling; and then we actually met, almost by – and I don’t believe in chances, right? We kind of crossed at a place in Miami and exchanged business cards. And ultimately he’s been with me ever since. But he was friends with Henke Kelner. And Henke…the Boom was over, and they were looking for production, and Henke said he would make me a cigar. And I could literally barely afford the samples. So I think I ordered a thousand cigars. And we sent – I bought these silver tubes, these silver mailing tubes. I bought 500 silver mailing tubes and I put two cigars in each and sent them to 500 retailers with no price list.”

“Henke said he would make me a cigar. And I could literally barely afford the samples.”

AR: “Henke and I have had a great relationship ever since. He is a true gentleman. And even the name, I mean I would never truly name a cigar Occidental Reserve. But I said, ‘Henke, what is it that you want to achieve out of this deal?’ He said, ‘I’d like to kind of build the name of my factory as well.’ It was called…Occidental, was the name of the factory. So we did Occidental Reserve. So that was a game changer for us because that kind of kept us in business.”

The Occidental factory (or OK, for Occidental Kelner) is also home to prestigious brands like The Griffin’s and Avo. The building is parked right next to the Davidoff factory in Santiago de Los Caballeros, Dominican Republic. Originally blended by Henke, Occidental Reserve still serves as a great “starter cigar” after all these years – not just because it’s an affordable bundle option, but because of its blend: mellow Dominican fillers clad in a caramel-colored Connecticut wrapper that smoke smooth and creamy.

#3. Alec Bradley MAXX

Alan: “ When it came to Maxx, we rolled all these large ring gauges: 60 by 6 3/8…we were one of the first people to ever roll large ring gauges. And at that time, I sold all the cigars for the same price, no matter what size they were…I think at that time it sold for five dollars at retail – all cigars. I mean we had like a 50 by 9 1/4, we had a 60 by 6 3/8…”

Yes, you read that right: 9 ¼” long. Alan said, “Yeah – we went ‘AA.’” It’s huge – you’re literally smoking two Robustos, which probably shakes out to be about a four hour smoke.

“We had one size that was called The Freak. And then I had a larger cigar, now they call it the Super Freak. Actually, I think they’re referring to it as the ‘Rick James’ right now.”

AR: “And people loved it. Today we have a large cigar out there, because we had one size that was called The Freak. And then I had a larger cigar, now they call it the Super Freak. Actually, I think they’re referring to it as the ‘Rick James’ right now. So Maxx was a big hit because we had all these large sizes that everyone could, at retail, buy for five bucks.”

To say the MAXX blend is diverse is an understatement: Honduras, Nicaragua, Colombia and Mexico all wave their respective flags in the filler blend; Costa Rica then brings a binder to the party, and the whole recipe gets together under a dark and oily Nicaraguan Habano wrapper. “When all is said and done,” we said in our 2015 CA Report on cigar tobacco countries of origin, it “results in a rich smoke that’s full in flavor yet still hovers around the medium mark in strength and body.” And as long as you wanted a big or bigger ring gauge cigar, MAXX was yours for five bucks. Times have changed, obviously.

#4. Alec Bradley Trilogy

Alan: “ We were working on different blends and ultimately we came out with three blends we really liked, but we were only going to launch one line. So I had three blends that we really couldn’t decide what was going to come out, or which one we were going to pick. So we had three blends. And then I had gone on a business trip. There was actually a fishing trip I was invited on, and there were a lot of cigar manufacturers – like four or five other cigar manufacturers on this trip. And they were all experienced in the business, so I just did a lot of listening. And somebody had said to me, “You know, you can’t just come out with another round cigar. There’s plenty in the market.” So that got me thinking. And then I went to, I remember thinking, no one’s done a triangular cigar. Maybe we should do that. Just kind of cool, and you know, back then 54 ring gauges were not the norm, right? There was all 50 ring gauge, 46…And what I found was is that you could roll a larger cigar, and if you pressed it into this soft sided triangle, it actually felt like a smaller cigar. So I didn’t know how to do it. So I actually created some angles, and did some drawings, and I went to Home Depot and they were demoing a DeWalt table saw. And I said, “Does this thing cut angles?” And he said, “Yeah, yeah. Pick some wood out of the pile, and I’ll cut it for you.” So I actually had them cut stuff on angles, and I glued them together – brought ’em back to the office, glued them together. And I had a press…I had a vice on one of our workbenches and started pressing cigars in the back of my warehouse.”

“Somebody had said to me, ‘You know, you can’t just come out with another round cigar. There’s plenty in the market.’”

AR: “ I actually still have it. I still have that mold. And then we went out to the factories and they thought it was nuts. And we did bright packaging – so we had three sizes, three sided, and three blends. And that was our Trilogy. And that was a huge game changer. You know, we get brightly colored packaging… We used to get e-mails like, ‘Oh, that doesn’t roll off my hot tub.’ People were really digging the whole piece, and that it was different – and that put us in hundreds and hundreds of stores.”

Sure, you’ve probably heard Alan’s story about Home Depot a few times before…but according to Cigar Journal, Ralph was reportedly unimpressed by the concept; he’d eventually be convinced. Trilogy would be released as cigars with 3 sides (a soft “triangle press”), in 3 wrapper options (Corojo, Brazilian Maduro and Cameroon), and 3 sizes (Robusto, Churchill and Torpedo). The line was retired a number of years ago – and back then, they smoked with medium body, full flavor and offered up thick, rich plumes of smoke.

#5. Alec Bradley Tempus

Alan: “In terms of giving us the exposure that any company wanting to grow would look for, Tempus was it. And actually, it was very interesting – I remember being with another cigar manufacturer, just at a cigar store, and I handed him a cigar. And he turned to me like, ‘You have something. This is special.’”

That “something special” was probably the Trojes wrapper, a Honduran Corojo that Alec Bradley now uses on a few of their blends. Their partners at Raices Cubanas (located in Danli) started a tobacco growing project in the Nicaraguan Valley – the nutrient-rich soil of the Jalapa region, but on the Honduran side of the border. That area is called Trojes, and that’s how it got the name. Alan said, “We use a term called ‘quantity of flavor’ in our offices – how much flavor can we get out of a tobacco. So it’s not necessarily about strength, it’s not necessarily about sweetness, it’s about quantity of flavor for us – and then we play with that. So we felt like this tobacco was rich and it was flavorful and it was very satisfying on its own, and something that we could blend with. It’s got a natural sweetness to it…[but] you don’t get a lot of that mildness out of it…We just think that Trojes is a very complete tobacco.”

“Tempus…that’s probably what I smoke the most of.”

AR: “So, I’ll tell you a story…we were up in the factory and we were blending it, and it was a small area. It was up in a little, like, conference area. And I’d say the room was maybe twelve by twelve, and there were five of us smoking and the door shut. And I’m smoking this little Corona Gorda of this blend that we did. And I started to, you know – there’s like not enough air, there’s not enough oxygen. And I said, ‘I have to excuse myself.’ Like…’Oh, you have to go to the bathroom?’ I’m like, ‘Yeah, yeah.’ I just needed to get out of the room and get some air. I was like, I can’t believe the impact of this tobacco. Again, a lot of Trojes, right? But I can’t believe the impact of the tobacco. And I said, what’s strange is like, if we’re in a room and we’re blending, I’m always the last one to light because I want to smell the aromatics in the air first to see if I like that. And then if I like that, and it’s alluring to me, then I light up and see where we are. But I just had a feeling like this cigar was special. It was different. So the next day, instead of smoking there – we smoked at our house across the street. And I said, ‘Hey, why don’t we sit outside.’ (laughs) And I lit up the cigar again, and I said, ‘We’ve never made anything like this before. This is where we need to go. This is the future of our company.’ And I turned to Ralph, who was sitting just on the other side of the table. I didn’t even say anything. He looked at me and I looked at him; and I just kind of shook my head, and he shook his head. And I’m like, OK – this is it. And that was the beginning of Tempus. That was our first Top 25 cigar of the year; and actually last year, Tempus took the number 5 cigar of the year. So that’s also probably the closest to my heart in terms of what it has done for our company. So Tempus. And that’s probably what I smoke the most of.”

One of the first Alec Bradley cigars to be made at Raices Cubanas, Tempus is a bold but balanced smoke. If you follow the cigar magazines’ ratings, I’ve seen scores for this cigar that range between 89 and 94; the Centuria (7” x 49 Churchill) was chosen the #5 cigar of 2017.

Bonus/#6. Alec Bradley Prensado

The #1 cigar of 2011…which pretty much speaks for itself. From our conversation:

John: So what happens when you get a #1 cigar – or, when one of your cigars is chosen as #1 cigar of the year? Do they make a phone call, do they send a letter, a singing telegram? What happens when it’s like, “Hey, good news, Alan…”

Alan: Yeah. None of that. Not one. I find out when everyone else finds out.

JP: Really?

AR: Yeah. So, and I’ll tell you that story. I remember the week when the Top 25 counts down, and I think it starts on a Tuesday. Ten, nine, eight…and we weren’t in there. And then Wednesday, it’s seven, six, five – and we weren’t in there. And I get to my office and we’re like, “No, we’re not seven, six, five.” Thursday is four, three, two – and we’re not in there. And I remember getting ready to go to work on Friday morning, and my wife says to me, “Hey, why don’t you stay? They’re announcing #1 at 10 a.m.” I said, “Yeah, I’m just I’m gonna go to work and, you know, hopefully on Monday we’re at least 11 through 25” – because that’s a great accolade to be there. And she said, “No, no – wait.” And I said, “I’m just, let me – I’m just going to go to work.” And she said, “No I want you to stay.” And my son came into the room with his laptop and just hit “refresh.” And at 10 o’clock…our band was there. Interesting, because I’ve told this story multiple times – but even telling it now, sitting here with you – you know, it’s…it’s emotional.

“I didn’t know that liquor stores were open at 10 a.m. – but I went there and I picked up two bottles of champagne for my office.”

AR: “ We all work hard. Cigar manufacturers, I mean, it’s a hard-working group of people. And for us to get that was pretty incredible. And I didn’t know that liquor stores were open at 10 a.m. – but I went there and I picked up two bottles of champagne for my office. And I walked in and everyone was going crazy: the phones were off the hook, it was literally like a scene out of Wall Street. You know, it was like, ‘You want how many? OK. OK. OK.’ And then I said to everyone, ‘Take 30 seconds, I want to congratulate all of you for all the hard work. But truth be told though, the work starts right now. And let’s go.’ And that was it.”

Alan said at the time it came out that Prensado was the most powerful cigar he’s sold; that’s probably due in part to the Trojes wrapper (like what’s used on Tempus, above). The cigar that made Alec Bradley a household name, Prensado cigars were originally produced at Raices Cubanas in only very limited quantities.

There’s much more to the Alec Bradley story…watch the 5 Cigars video above, and you’ll get it all: some of the behind-the-scenes secrets on how Alec Bradley cigars are blended, and what else Alan is smoking right now; how the next generation of Rubins – Alec and Bradley – have come to the table with their first cigar, called Blind Faith, plus a bit about AB’s new-for 2018 cigars like Medalist and Prensado Lost Art – along with what new ideas Alan has up his sleeve for the next Alec Bradley brand project.

With thanks to Alan Rubin.

Five Cigars that Made My Career is a recurring Cigar Advisor series. Comments are welcome, including a mention of your favorite Alec Bradley cigars.