Once the cigar was lit, I got some pretty unique flavors. Chocolate, earth, and some sweetness were present. The sweetness seems to really pop when I take a sip of the Henry McKenna. Speaking of which, the bourbon is a really good bourbon for the money. A bottle will run you about $20. The nose is loaded with sweet caramel, corn, and oak, balanced with a bite of alcohol. The flavor is really sweet. Cherry, vanilla, and oak are all present with a slight heat from the alcohol on the finish. This bourbon is bottled at 90 proof so I suggest adding a couple drops of water and letting it sit for 3 minutes. It really opens up the flavor.
Half way through the 50 Years, and the flavors stay pretty consistent. I'm surprised that this cigar doesn't have much spice to it. I think this cigar could use a little spice to really make it a great cigar, but other than that, the flavors are really good.
Tonight's pairing was really enjoyable. I think the Henry McKenna 10 Year would pair well with most full bodied cigars. I think it would really overpower mild cigars. I highly recommend you pick up a bottle if you enjoy bourbon :-)