Woodford Reserve or Buffalo Trace could be paired up against a medium smoke - that's not too difficult. Probably something like a Gurkha Legend would be okay. Personally, I would prefer something like a Fuente Don Carlos, or a Cuesta Ray Centro Fino.
But I would say that if he's looking to pair a cigar against a "bold" flavor like "dark robust coffees", it's going to take something that has some "meat" - something strong/bold. Probably something pretty full bodied, wouldn't you think? La Flor Dominicana comes to mind, right off the top of my head...
So - Mike - what is this "Cigars in 60" all about? Tell us about it!
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