Whether you’re a casual admirer of America’s cardinal spirit—bourbon—a die-hard enthusiast, or even an abstaining onlooker, you’ve no doubt heard the name “Pappy’s” being tossed about increasingly in recent years. The name stems from the most notorious bourbon the world over: Pappy Van Winkle’s Family Reserve. Cigar Dojo ranked our selections for The 5 Best Bourbons in 2013 and Pappy’s topped the list, scoring both the number one and two spots (20-yr and 15-yr, respectively).

Pappy Van Winkle’s Family Reserve is distilled by the Old Rip Van Winkle Distillery, a subsidiary of Buffalo Trace Distillery, located in Frankfort, KY. The collection spans three different expressions (15 year, 20 year, and 23 year), as well as other variants such as Old Rip Van Winkle 10 year, Van Winkle Special Reserve (Lot “B”), and Van Winkle Family Reserve Rye. These whiskeys undisputedly lead the charge of America’s (and the world, to an extent) current obsession with bourbon/whiskey.

SEE ALSO: Best Bourbon 30 Dollars And Under

Without diving too deep into the exhaustive lore behind Pappy Van Winkle (this is a cigar review, after all), the basic premise is that this collection of family-controlled whiskeys has become one of the most sought-after commodities across the country over the past few years. While bottles once gathered dust and could simply be plucked from store shelves like sliced bread, the hype began to build in the mid-2000s—ramping up year after year until the wheat-heavy liquor reached secondary market prices of roughly 1,500% greater than MSRP! Of course, the whole issue arises from a disproportionate ratio of supply vs. demand, but bourbon poses the unique dilemma of time being the operative ingredient (hence the name, Rip Van Winkle), meaning it could be some time before these two factors reach a more sensible balance.

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Capitalizing on the surge of popularity in the Pappy brand, great granddaughters of Julian “Pappy” Van Winkle (i.e. the original Pappy) formed Pappy & Company in 2013 as a means to offer merchandise and other collaborations bearing the Pappy Van Winkle imagery. The most notable of these collaborations is a partnership with cigar manufacturer Drew Estate, where Pappy & Co. began offering Van Winkle-inspired cigars through their website in 2014.

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Pappy Van Winkle Tradition Belicoso Fino Breakdown

  • Wrapper: Ecuadorian Habano Oscuro
  • Binder: Indonesia
  • Filler: Nicaragua | Dominican Republic
  • Factory: La Gran Fabrica Drew Estate (Nicaragua)
  • Production: Limited/Seasonal (Drew Diplomat Exclusive)
  • Vitola: 5″ x 50 “Belicoso Fino”
  • Price: $24.60 (MSRP)

Drew Estate first announced the Pappy Van Winkle’s Family Reserve cigar in 2014 to the delight of cigar/bourbon enthusiasts the world over. Interestingly, the cigar’s details were kept somewhat ambiguous, with fans not knowing whether the blend had been aged in Pappy Van Winkle bourbon barrels or if they were simply intended to be paired with the bourbon. After the announcement, the cigars went through many changes, including the name and even the blend. The cigars are now known as Pappy Van Winkle Barrel Fermented, and use a unique blend that includes a Kentucky Fire Cured wrapper (as one of the cigar’s two wrappers) that is barrel-fermented—where the leaves are highly compressed in wooden barrels using screw jacks—a technique found in certain pipe tobaccos.

Pappy Van Winkle Barrel Fermented cigars were made in very small batches at Drew Estate’s factory in Nicaragua, with the cigars selling out quickly through Pappy & Co. when they were periodically made available. The cigars have since become readily available, with Pappy & Co. stating “we have invested even more into our exclusive manufacturing partnership with Drew Estate. […] No pre-ordering, no long wait-times and no need to hide them away for special occasions.”

At IPCPR 2016, Drew Estate showcased a new blend under the Pappy name. The cigar’s name/blend/appearance had not been finalized, but was advertised as making use of a more traditional smoking experience. One year later, the cigars officially debuted at IPCPR 2017 under the name Pappy Van Winkle Tradition. Differing from the original Pappy cigars, Tradition uses a traditional blend, crafted by Drew Estate Master Blender Willy Herrera in 2010.

I remember it like yesterday. In 2010 when JD and I talked about me joining Drew Estate, we flew down to La Gran Fabrica to test my blending style in two days of non-stop creating. I ultimately produced 3 blends, one of which eventually became the Herrera Estelí. When I heard the news that Julian Van Winkle had selected one of my three original blends from my first trip to Nicaragua, I was humbled to say the least.Willy Herrera, Master Blender of Drew Estate

Unlike the original Pappy cigars, Pappy Van Winkle Tradition is being offered nationwide, where authorized “Drew Diplomat” retailers received small allotments of the cigars beginning on September 30th, coinciding with “Pappy Day” on October 1st (when Old Rip Van Winkle traditionally reveals release details to wholesalers for their annual whiskey release).


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Arriving in seven sizes (three of which are exclusives), Pappy Van Winkle Tradition is an ultra premium in terms of pricing, ranging from $15 to $25 per cigar (compared to $13 to $17 of the Pappy Van Winkle Barrel Fermented cigar). The look is similar to to all other Pappy-branded products, showing an old photo of Julian Van Winkle smoking a cigar. The bands feature a new red color scheme that is more akin to the 20-year vintage of Pappy Van Winkle’s Family Reserve bourbon. There is also a new sub-band that identifies the cigar as “Tradition.” The look is about what you’d expect, however, I can’t help but notice the lack of embossings, metal foils, and other “fancifications” I’d expect to find on a cigar of this price.

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Despite not being the largest size, the Belicoso Fino is the priciest of the bunch—most likely due to its more intricate shape. The cigar’s wrapper is slightly darker than medium brown, about Colorado shade (a little darker than the cigar’s sister blend, Herrera Estelí). There is a smooth, lightly fuzzy feel to the wrapper, showing few veins and visible, yet flush seams. The bunch is quite firm, giving the cigar a hard, papier-mâché-like exterior.

On the wrapper, there are notes of hay, cedar, and citrus, and the foot aroma adds chocolatey nuances to the mixture. With a double guillotine cut, the pre-light draw shows a medium-firm resistance and notes of corn chips, cherry fruit, and an underlying terrarium tone.

Smoking Experience

Pappy Van Winkle Tradition Belicoso Fino lights up with spicy notes of raw peppercorns. The second puff is sweeter, and the third sweeter still. Each draw reveals a little more to the cigar’s profile, with eventual notes of citrus, cedar, sweet butter, and tangy sourdough bread. The profile is bright and classic, being fairly mellow in overall body.

The cigar’s construction is exemplar of the La Gran Fabrica Drew Estate factory, gathering roughly two inches of stark white ash before falling from the cigar. The draw seemed slightly more firm than ideal on most samples, though this could be remedied with a deeper cut—a common benefit of the belicoso vitola. Even still, the smoke output was around medium and was satisfactory throughout.

Pappy Van Winkle Tradition Belicoso Fino cigar ash

Nearing the halfway point, there is an added zip of spice in the nostrils, accompanied by a semi-sweet note of anise/black licorice. The smoking experience is classic and clean, having a medium-minus strength, medium flavor, and medium body.

In the final third, the Tradition goes out with a bang, boosting the spice and adding fresh notes of coffee liquor, toffee sweetness, and toasted bread. The cigar has a long burn time for its size and retains its desirable flavors longer than expected, allowing most samples to be nubbed farther down than I’m often willing to go.

Pappy Van Winkle Tradition Belicoso Fino cigar smoking

Would I Smoke This Cigar Again?

Yes and no. Does Pappy Van Winkle Tradition have enough enjoyable flavors, adequate draw and construction, and overall enjoyment to warrant future tastings? Absolutely, but it’s price is hard for me to get around. Sure, there are a handful of luxury-priced cigars that I can recommend without pause (OpusX, Plasencia Alma Fuerte, Illusione Haut 10, and a handful of Padróns, to name a few), but this isn’t exactly the category that most cigar smokers can swing on a whim. In this category, the cigar needs a SERIOUS “it factor” to set itself apart, something you can’t exactly find elsewhere for a much lower price and ease of procurement. In my opinion, the Tradition smokes quite similarly to Drew Estate Herrera Estelí, which is available in many more formats, easily found in most humidors, and at a far more affordable price.


With the modern style of tailor-fitting cigars with their proper pairings (SEE: Imperial Stout Barrel-Aged), Pappy Van Winkle Tradition will be at the top of most die-hard enthusiast and collector’s lists. If you are lucky enough to have your own bottle of Pappy’s (congratulations), you’ll have a higher incentive to spring for the box purchase here. If you’re in reach of a friend or local bar that has Pappy’s AND allows smoking, this will likewise be a no-brainer purchase, simply for the thrill of experiencing the colliding of two of the best craft industries the world has to offer! (aka cigars and bourbon). Or, you know, do it for the bragging rights…

If you’re already a fan of Pappy Van Winkle’s Family Reserve bourbon, you’ll probably know the juice makes practically every cigar taste better. This is also the case with the Tradition cigar. When pairing Pappy 20-year, I found a much (MUCH) longer and sweeter finish. The citrus notes in the cigar and bourbon are both magnified, bringing out an enhanced bubblegum-like finish and velvety mouthfeel. Neither the cigar nor bourbon overpower one another, being a perfect match in that regard. Although, Pappy’s bourbon did outshine the cigar in terms of overall flavor and complexity.

If you are without any form of Old Rip Van Winkle bourbon, there are other options that will give you “the gist of it.” Most notably, W.L. Weller will be your best bet. This is a wheated bourbon from Buffalo Trace that uses the same recipe as Pappy’s. There are a few different versions of this available, and it is often considered among the best values on the market. And if you cannot find Weller, simply go for another wheater-style bourbon, such as Larceny, Rebel Yell, or even Maker’s Mark.

  • The Tradition blend is said to be one of the three original blends created by Willy Herrera for Drew Estate, with the Herrera Estelí cigar being another of the three.
  • Pappy’s bourbons feature a wheated mash bill (often called “wheaters”), where wheat is used in place of rye for the secondary grain (joining corn as the first and barley as the third).
  • Pappy’s and other rare bourbons are typically released in the fall, with Oct. 1st signaling the start of the festivities (aka “Pappy Day”).
  • The actual recipe of Pappy’s is not what makes the bourbon special, as it shares the same mash bill with W.L. Wellar. It’s “unattainable” status plays a role, as does added age (wheated bourbons are said to handle longer aging better than their rye-based siblings), and the fact that the Van Winkle’s hand-select every barrel to be dumped for each year’s release.
  • Images for this review feature the Cigar Dojo NEAT Whiskey Glass—the optimal vessel for spirit tastings and a glass that is increasingly being used for official, spirit-tasting competitions.
  • Pappy Van Winkle’s Family Reserve 20-year (2012 release) was used in photos and for pairings for this review.
  • In my personal opinion, I rank the Old Rip Van Winkle whiskeys as such: 15-year > 20-year > Van Winkle Rye > 23-year > 12-year > 10-year.
  • Jonathan Drew often lists Van Winkle Family Reserve Rye as his preferred pairing with Pappy Van Winkle cigars.
  • Smoke Time: 1 hour, 30 minutes
  • Pairing Recommendation: Pappy Van Winkle’s Family Reserve (or any of the six Old Rip Van Winkle offerings), W.L. Weller (any of the four variants), wheated bourbon (last resort)
  • Purchase Recommendation: single cigar

Pappy Van Winkle Tradition Belicoso Fino cigar nubbed

Images without Cigar Dojo watermark were provided by Drew Estate

Pappy Van Winkle Tradition Belicoso Fino
Pappy Van Winkle Tradition is the second release from Drew Estate and Pappy & Company, following the duo's "non-traditional" release in 2014. The concept for Tradition is front and center, offering a more traditional smoking experience for the connoisseur; made to pair well with the Van Winkle family's sought-after collection of bourbons and rye (or any American whiskey, for that matter). The smoking experience is as advertised, unveiling a classic profile and medium body that pairs great with wheated bourbon (Pappy Van Winkle’s Family Reserve 20-year was used for review). The cigar's bright profile of citrus, cedar, butter sweetness, black pepper, and tangy sourdough bread balances quite well with its bourbon counterpart, with neither cigar nor bourbon overpowering the other. Ultimately, it's the cigar's lofty price point and a lack of a true "it factor" justification that makes for a difficult recommendation. On the other hand, the cigar's fun concept and pleasing, clean and balanced profile warrant a at least a test run—make it a celebratory smoking session.
  • Pairs great with bourbon
  • Clean, classic profile can be enjoyed by most anyone
  • Solid construction, ash lasting roughly 2"
  • High price point
  • Expected more luxurious presentation for price
  • No real "it factor"
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