I’ll begin this post with a short, but important statement. Like alcohol, tobacco should only be enjoyed by adults of legal age; moreover, it should be enjoyed responsibly and in moderation.

Whiskey and cigars have shared an association for generations. Wild Turkey’s Jimmy Russell often recounts that when he first hit the road to introduce new consumers to his whiskey, bourbon’s popularity was limited to older gentlemen who played cards and smoked cigars. Since that time, the landscape has changed dramatically (thanks in part to Jimmy’s travels), with bourbon’s admiration extending to a large and diverse audience. The same could be said for premium cigars.

Last summer, the cigar bug bit me. There was no pre-existing desire, or even mild curiosity, to try one. I just happened to be shopping for my father-in-law and figured a fancy cigar would suffice. I had no idea that I’d soon be returning to the same store to shop for myself, nor did I have any idea that I’d be spending hours reading, researching, and watching YouTube videos about these mysteriously fragrant “sticks.” Yet, here I am.

Similar to my whiskey journey, my cigar journey kicked off cluelessly energetic. Of course, I sought advice and recommendations from friends and trusted associates, but even with their help I was navigating a new world. There were, however, correlations to whiskey I could relate to. Primarily, premium cigars are artfully crafted from natural ingredients to create a wide range of flavor profiles. How these profiles are achieved depends on various factors, but just like crafting a fine whiskey, there are no shortcuts.

It was a start. I had a lot to learn – still do – but I was well on my way.

Profiles & Pairings
Alec & Bradley’s Kintsugi

Thanks to my incredible whiskey buddy Matt Porter (a/k/a ADHD Whiskey), I was introduced last year to Alec Rubin of Alec Bradley Cigars. Immediately, Alec was welcoming, offering valuable industry insight and shedding much-needed light on the trickier points of cigar enthusiasm. It was precisely the connection I needed, arriving at the perfect time, no less.

Alec and I have spent a lot of time chatting over the last few months. Sometimes it’s a simple sharing of an opinion on a specific cigar or whiskey, other times it’s an in-depth conversation on how and why something is the way that it is. But it’s never boring conversation. And the best part about it? Alec Rubin is a huge Wild Turkey fan. Like I said, never a boring conversation.

Considering our shared fandom for all things Russell, as well as our inclination to enjoy Kentucky’s Finest with a quality stick, it only seemed right to interview Alec for the blog. Besides, I’m guessing there’s more than a handful of Wild Turkey fans who view themselves as cigar aficionados, or at the very least dabble enough to appreciate his perspective. And if you’re not a cigar fan, you’ll likely find value in Alec’s whiskey suggestions. The way I look at it, the opinions of an experienced palate, regardless of profession or area of focus, are often opinions worthy of consideration.

RB101: Alec, tell me a little about yourself, Alec Bradley cigars, how it started, when you got involved, and where things are now. Also, touch on Alec & Bradley and how it’s different from Alec Bradley Cigars.

Alec Rubin: I’m one of the namesakes of the family-owned and -operated Alec Bradley Cigars. My father, Alan, founded the company in 1996, naming it after me and my brother, Bradley. I started working for the company about ten years ago, learning how we operate from the ground up. During my first summer, I worked in the warehouse, packing and shipping. Later, I went into phone sales, working on private labels and executing graphic design. Currently, I work on blending new releases, as well as working closely with our territory managers and retail partners.

I’m very fortunate because, on the blending side, I enjoy building and honing in my palate. And on the sales side, I love interacting with our accounts and brand advocates. My brother and I also started our own project about four years ago called Alec & Bradley, and we’ve been honored to have our cigars recognized in several cigar-focused publications. We had a goal to go a bit off script from the rules our father created around Alec Bradley. I think that Alec & Bradley cigars are a bit riskier in their presentation. They speak to a more niched demographic as well.

And even if you don’t match the right cigar with the right whiskey, who cares? You’re still smoking cigars and drinking whiskey!

Alec Rubin

RB101: I see common ground with Wild Turkey and Alec Bradley, both having multi-generational family ties. What’s it like working with family?

AR: Working with family is definitely rewarding and challenging. There’s no better feeling than accomplishing and winning together. Yet, I believe emotions run higher with family members than with other co-workers.

RB101: What’s your preferred “everyday” Wild Turkey expression? And for a cocktail? How about special occasions?

AR: I always keep Wild Turkey 101 and Rare Breed on hand. Which one I grab is based on how few steps I have to take to reach the bottle. I keep 101 downstairs in a decanter so I can find it quickly when making cocktails. But my favorite Wild Turkey bottles are definitely the Master’s Keep collection. I have all of them except the 17-year, which I believe was the first one. My favorite is probably Cornerstone just because it’s such a unique and tasty rye.

RB101: What’s your opinion on pairing cigars with whiskey? Do you prefer it over other commonly paired beverages (coffee, soda, wine, etc.)?

AR: There’s no better pairing than cigars and whiskey, in my opinion. The way they complement each other is fantastic. And even if you don’t match the right cigar with the right whiskey, who cares? You’re still smoking cigars and drinking whiskey!

RB101: When you’re crafting new tobacco blends, do you ever consider how that blend might work with whiskey (or other beverages)?

AR: I generally don’t worry if a cigar is going to pair with whiskey when I’m blending [tobacco]; it’s normally not my focus. Though I am working on a cigar in collaboration with Bardstown Bourbon Company. That cigar is definitely being blended to pair perfectly with their whiskey.

Profiles & Pairings
Alec & Bradley’s Gatekeeper

RB101: I’m giving you a challenge today. Pick three Wild Turkey expressions. They can be bourbon, rye, or even liqueurs like American Honey. Which Alec Bradley (or Alec & Bradley) cigar would you pair with each and why?

AR: I find pairing to be subjective and very personal. What’s right for me may not be right for someone else, but I enjoy guiding others as they test their palates. The truth is, when you come across a good pairing you know it!

This first pairing might not seem obvious to some, but I really enjoy it. Wild Turkey Master’s Keep Revival and Alec Bradley Magic Toast are each “off profile” [for their brands], but come together nicely as a pairing. Both have a level of fruity sweetness with hints of oak.

The second pairing I’ll phone in a little bit, but in the best way possible. I’m going with a whiskey that works with many cigars, and a cigar that works with many whiskeys, each with predominant notes of spice and toffee – Russell’s Reserve Single Barrel Bourbon and the Alec & Bradley Gatekeeper.

My last pairing might be the most classic. Wild Turkey 101 and Alec Bradley Tempus Natural just seem to work together. The classic whiskey flavors from Wild Turkey 101 balance nicely with the classic cigar flavors of the Tempus. The Turkey has a nice rye bite to it, and the Tempus complements it with sweetness and creaminess. Overall, a very enjoyable experience.

RB101: One last question. If you could offer any advice to whiskey enthusiasts exploring the world of premium cigars for the first time, what would that be?

AR: Try everything. Don’t let other people tell you what you should or shouldn’t be smoking. And never v-cut a cigar.

I’d like to thank Alec Rubin for taking the time to answer my questions and for sharing his favorite Wild Turkey and Alec Bradley pairings. If you’re curious about Alec Bradley or Alec & Bradley Cigars and what they have to offer, visit AlecBradley.com. You can also find them on Instagram @alecbradleycigar and Twitter @alecbradley.

Whether it’s with a quality cigar or pour of your favorite whiskey (or both), never underestimate the benefits of relaxation and quiet contemplation. Time may be precious, but if you put off the moments to appreciate it, it’ll inevitably pass you by. Cheers!


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