Cigar Review: Drew Estate Pappy Van Winkle Tradition

DE Pappy Van WinkleVitola: Belicoso Fino
Size: 5″ x 50 ring gauge
Price $24.99 MSRP
Obtained From Drew Estate as a review sample


The name Pappy Van Winkle elicits rarity and expense in the bourbon world.  When I first heard about it I was wondering if DE was aging the wrappers in old Pappy barrels.  Luckily they didn’t do that as I haven’t had a barrel aged cigar I’ve liked.  However it looks like they did keep the rarity and expense parts as only 2,300 10-count boxes of each of the four sizes were sent out to all of the retailers in the US with prices ranging from $15-$25 per cigar.  Jon did a review of this cigar and you should check it out here.  I smoked two of this size and at least one other size (maybe two) before this review.


The top band is familiar if you’ve seen on the bottles of bourbon bearing the Pappy Van Winkle name.  The bottom band labels it as the Tradition blend.  I did some research and it looks like there is a barrel aged cigar as well only sold through Pappy store.  The wrapper is a medium brown in color with a hint of red to it.  The wrapper is also sort of smooth with some oils and very little tooth.  When I gave it a squeeze it had a slight amount of give without any soft spots.  When I put my nose to the wrapper I noted the aroma of hay and leather with wood and leather coming from the foot.  After clipping it and taking a cold draw I got a good draw with hints of wood and sweetness.


It starts off with a good amount of spice on the tongue and retrohale.  A few puffs in I started to get some wood, green herbal and leather flavors with a slight sweetness on the finish.  The cigar starts off at the upper end of medium strength and the spice died down a lot towards the end of the first third.  When I got to the second third it really didn’t change a whole lot except for the spice was pretty much non existent.  The final third saw the spice come back a bit but it never moved out of medium strength.  I noted lots of wood, leather, earth and tobacco flavors in this final third.


The draw was great throughout.  The burn line was wavy and needed a little correction, but that could have been my lighting it.  The ash was a little flaky and I was brushing myself off.


While I know the name has come cachet but I didn’t see where the $25 cost comes from.


Well Jon and I have very different opinions of this cigar, he really like it and it doesn’t do anything special for me.  There wasn’t anything bad mind you but it didn’t really grab me even if the price wasn’t an issue.  I didn’t get to pair this cigar with any of their bourbons so I don’t know if that might have made my experience better.  If you’d like to see for yourself what this cigar is like head on over to as they still have a few of them left.


Prelight: 2/2
Construction: 1.5/2
Flavor: 3.5/5
Value: .5/1
Total: 7.5/10

Keith Hollar

Keith has been a cigar enthusiast since 2003 and it's rumored that he remembers details about every single cigar he's ever smoked. He wrote for Tiki Bar Online for four years before co-founding Leaf Enthusiast. Twitter: @Keith1911

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