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A Snifter and a Smoke - Cigar Pairing

Updated: May 24, 2019

Whiskey and Cigar Pairing – May 21, 2019 – Leon’s Steakhouse Longview

with Travis Pyeatt of The Smoking Aces Mobile Cigar Lounge


Tonight we took part in a special pairing of a cigar and whiskey. As Travis explained, a cigar changes on the palate throughout the smoking experience. When closer to the Foot (the end you light – for those of us like myself that are learning as we go along), the spicier, more robust flavors dominate. The middle third of the cigar becomes milder, with the spice (for the bolder cigars) dropping away behind an insulating buffer of cooling ash. Finally, the part of the cigar towards the cap (the part you put in your mouth) brings with it a still milder, possibly even sweeter character to bear.


Tonight’s cigar was from Garcia & Garcia – My Father – Le Bijou 1922. This is a Nicaraguan Puro (puro meaning all leaves grown in the country of origin). It was rated the #1 cigar of 2015. The cigar has a Robusto size of 4 ½ inches and 50 ring gauge. This is the second release from the “My Father” line and has a Habano wrapper, which provides a decent amount of spiciness. In fact, it is one known to provide the Garcia “shower of pepper” upon the first light. It has been described as having a full body with a nose of chocolate and leather with a bit of a hay smell on the foot.


We learned a bit, too, about where some of the nose and taste characteristics come from with cigars. Thicker tobacco leaves that get more sun tend to be spicier. The construction of the cigar consists of three different types of leaves:

  • The Filler makes up the meat of the cigar and

  • Is pressed into place with the Binder leaves

  • Finally, the Wrapper leaves form the outer skin and contribute more to the overall character the smaller the cigar’s diameter

Thicker cigars are therefore known to be a bit more bland due to the prevalence of the filler flavor over the heartier wrapper leaves.


When pairing with whiskey, the general rule is to pair body to body. For tonight, the idea was to reverse the typical whiskey flight to start with a heavier elixir and move towards a milder offering in order to match the mellowing as the cigar burns.


We therefore began with Little Book Chapter 2. Little Book is named after the grandson of Booker (Jim Beam’s son), Freddie Noe – a 30 year old kid in an adult candy store. His first chapter began as an experiment to blend corn, malt, and rye whiskey (which didn’t work out so well) and ended as more of a typical bourbon. This time around he was determined to make a special rye. After 36 attempts, he arrived at “Noe Simple Task”, a blend of an 8 year old Kentucky rye, an 18 year old Kentucky rye, and a 40 year old Canadian rye (to sweeten the story). It comes out as a 119 proof rye with a nice blend of spicy and sweet robust enough to blend well with the peppery Garcia cigar.


What we realized from the pairing was that the rye actually mellowed the cigar, and the cigar evened out the spice of the rye. With a weaker cigar, the rye might have offered a heavier hand, and with a less robust whiskey the cigar might have overpowered the juice. But it turns out, these were a very good match for each other and a model for how you might try to work your own pairings.



As we approached the mellower middle of the cigar, careful to let the ash fall only when ready (another learning from this evening), we move to the 92 proof wheated bourbon Larceny from Heaven Hill. The mash bill of Larceny is undisclosed, but they promise "at least 1/3 more wheat than competitors". This bourbon is a lot sweeter and more mellow than the Little Book rye. It has some of the citrus character inherent to many wheated bourbons. It was noted that this bourbon has a bit of a thin mouthfeel, but when paired with the cigar, there is an addition of body that once again demonstrates the power of a good combination. Once again, we were in agreement that the sweeter, milder bourbon made a good match with the milder middle of the Garcia.


A little about the history of Larceny. John E. Fitzgerald originally set up the distillery along the Kentucky river and sold bourbon to the rail lines. During prohibition, however, he sold it to Pappy Van Winkle. During Prohibition, bourbon was still produced, but it was sold for medicinal purposes. It was also closely monitored by the government. In fact, each distillery had a government official assigned to guard the rickhouse. He had the only key - so when the owner of the distillery wanted to go into the rickhouse, he had to be accompanied by this official. By stroke of non-divine intervention, the man with the key at the Fitz distillery just happened to be John E. Fitzgerald himself. And it was said he even had his own private stash of the best bourbon from the rickhouse in a special area called "old Fitz's room". But Pappy Van Winkle knew about "old Fitz's" private stock and was skimming a little for sale on the side - a brazen act of Larceny against a government official in a dangerous time for bourbon sale period. Thus the Heaven Hill branding of this wheated bourbon with the Larceny name and Key logo.


Ah, this tall tale has brought us to the last third of the cigar. Travis describes this bit as a little "meatier". He pointed out to us that the ash is very white on this cigar - evidence of the volcanic soil in which the leaves grow. In fact, you can learn many things from the ash itself, but you must let the ash tell the story by only allowing it to fall from the guitar when it's ready to do so. And how it falls can give clues to the construction of the cigar - the tightness of the leaves and even the character of those used for the binder and filler.


I also learned something at this point that will forever change cigar smoking for me. Travis taught us about the Retrohale. This is the process of forcing the smoke up through your nasal cavity and out through your nose to immerse your palate with the flavor of the cigar. You don't inhale into your lungs, but there is a breathing in element as your force it up through your nose. My first retrohale was a bit more than I was ready for, and I felt the burning of getting water up my nose. But once I got it right, it completely changed the character of the cigar for me. Suddenly the tanniny bitterness I sometimes experience at this point gave way to a velvet sweetness, almost a warm vanilla flavor. My enjoyment of the cigar turned to a craving - an urge to drink up the flavor of the smoke. If you have never tried this with a cigar, I can't recommend it enough.


But enough about drinking smoke, what about the bourbon? We had what I consider a treat for our final selection: Basil Hayden's 2x2. We had previously tasted Basil Hayden's with the Jim Beam flight, and I knew there was sweetness in store for us. In this case, the 2x2 refers to a 6 year bourbon, 13 year bourbon, 7 year rye, and 5 year rye all blended together to form a medium bodied and sweet concoction. Tasting notes included cherry, banana Laffy Taffy, and even a bit of clove spiciness. The only drawback to this offering is the 80 proof aspect that ultimately leaves many unsatisfied with a very brief aftertaste. Ultimately, the cigar had to step up to beef up the aftertaste, creating a good finish to the three whiskey cigar pairing.


This one has another interesting back story in the Hayden family itself - the first of which was knighted in 1190! The Catholic family made their way stateside and settled in the Virginia Colony. This was subsequently followed by moves to Maryland and then Kentucky. In Kentucky Basil Hayden began distilling a heavy rye for the army. The Basil Hayden name eventually became synonymous for this high rye flavor, and it was this character that Jim Beam eventually picked up in Basil Hayden. To remain true to this recipe, they created the Old Grand-Dad line (that's Basil Hayden Sr. on the front of those bottles). But they took the Basil Hayden line further, creating a more top-shelf look with the bottles and creating special blends like the 2x2, the first of its kind.


And that's how we do a great pairing - a little knowledge of the craft, a little knowledge of the history, a little discussion on the flavors, and a little levity overall. Also, I couldn't leave without buying another one of those masterful Garcia & Garcia's. I look forward to smoking one on the beach in St. Kitt's next month!


Until next time, keep your bourbon warm, your cigar hot, your wit sharp, and your mind open.


Erik Dunham - ETBS