In this smokey, robust conversation with cigar and whiskey expert Maggie Kimberl (@lougirl502), some of the topics we discuss include:

A working definition of "cigar blend whiskey," plus some specific thoughts on the ideal proof point for these types of blends.
The two primary pairing strategies that you can use to pair any two items in the flavor world, whether you're talking about wine and food, whiskey and cigars, or even building the perfect charcuterie bite.
How to think about "flexibility" in the whiskey and cigar pairing space. Essentially: is a given whiskey designed to pair with a wide range of cigars, or has a blender designed it to pair with one cigar in particular?
Then, we look at cigars. We talk about how a cigar is going to change as you smoke it, how to think about size metrics like shape and ring gauge relative to other factors like robustness and country of origin, and the best way to leverage online reviews and your local tobacconist to help you navigate the scene.
We wrap up by talking about some of the more recent trends and collaborations in the whiskey and cigar world, exploring certain ways in which cigar blends and pairing collaborations are getting better, and even more complex at the same time.
Along the way, we cover what your breakfast beverage of choice says about your taste in cigars, which $25 bottle of whiskey Maggie ended up pairing with a $1000 cigar, the results of her 7-month Manhattan study, and much, much more.