There’s a tendency, when people first start exploring cigar and spirits pairings, to assume that better always means more expensive. The most prestigious bourbon must pair best with the most premium cigar, the logic goes. Pappy Van Winkle and a Davidoff Royal. Stagg Jr. and a Cohiba Behike.
That logic falls apart pretty quickly when you actually try it. A $400 bottle of bourbon and a $50 cigar will, more often than not, fight each other for attention rather than complement each other. Both are demanding, both are showing off, and the pairing becomes a competition of intensities rather than a conversation of flavors.
The best pairings, in my experience, are usually more democratic. They’re about complementary character, not a stack of price tags. And one of the most reliable, accessible great pairings I’ve found is Buffalo Trace bourbon and a full-bodied Nicaraguan cigar.