It’s October, which means if you are a fan of Pappy Van Winkle whiskey, it’s time to get ready to play the lottery at your local liquor store or pay a lot of money for 750ml bottles that say Van Winkle.

Few products have garnered the cult-like following as Van Winkle bourbon and even fewer have been able to then translate it into mainstream success. For a variety of reasons, the Van Winkle family cannot just suddenly bottle enough Pappy Van Winkle to meet demand, but the company can make a lot of other products that say Pappy on it.  The family has a separate company called Pappy & Co. that handles licensing deals, including a partnership with Drew Estate.


A few years ago, the company released the Pappy Van Winkle Barrel Fermented Cigars, a two-size line that was sold on the Pappy & Co. website. This year, the pair of companies teamed up for the Pappy Van Winkle Tradition, a cigar that will be the available at select tobacconists nationwide.

No, the cigar is not aged in barrels that once held Pappy Van Winkle nor any other bourbon for that matter. It actually has little, if nothing, to do with bourbon outside of its name. Rather, it’s a cigar that Julian Van Winkle, the president of Old Rip Van Winkle Distillery, liked.

The Pappy Van Winkle Tradition is said to be one of the first blends that Willy Herrera blended at Drew Estate, using an Ecuadorian habano oscuro wrapper, an Indonesian binder and fillers from the Dominican Republic and Nicaragua. Drew Estate gave Van Winkle a bundle of the cigars as a gift and he liked them so much, they chose it for the next release.

It is offered in seven sizes, though two are not available for purchase.

  • Pappy Van Winkle Tradition Coronita (4 x 46) — $14.60 (Boxes of 10, $146)
  • Pappy Van Winkle Tradition Corona (5 1/2 x 44) — Jonathan Drew/Julian Van Winkle Exclusive
  • Pappy Van Winkle Tradition Belicoso Fino (5 x 50) — $24.60 (Boxes of 10, $24.60)
  • Pappy Van Winkle Tradition Robusto Grande (5 1/2 x 54) — $21.60 (Boxes of 10, $216)
  • Pappy Van Winkle Tradition Toro (6 x 50) — $23.60 (Boxes of 10, $236)
  • Pappy Van Winkle Tradition Lonsdale (6 1/2 x 44) — Drew Diplomat Reward Event-Only
  • Pappy Van Winkle Tradition Churchill (7 x 48) — $23.60 (Boxes of 10, $236)

The cigars are highly limited with a Drew Estate representative telling halfwheel, most stores will only receive less than a handful of boxes of each size. The plan is to have the cigars ship each October to coincide the Pappy Van Winkle bourbon shipment. Drew Estate also hopes, like Pappy the bourbon, the cigars sell out quick and aren’t available until next year’s shipment.


Charlie Minato

I am an editor and co-founder of Media, LLC. I previously co-founded and published TheCigarFeed, one of the two predecessors of halfwheel. I handle the editing of our written content, the majority of the technical aspects of the site and work with the rest of our staff on content management, business development and more. I’ve lived in most corners of the country and now entering my second stint in Dallas, Texas. I enjoy boxing, headphones, the Le Mans 24-hour, wearing sweatshirts year-round and gyros. echte liebe.