Lots of people like a cigar with a glass of bourbon or other whiskey. This has been restricted to the idea of smoking the tobacco when drinking the whiskey. To my knowledge, while there has been some talk here about using whiskey to flavor tobacco (and such tobaccos certainly exist), the reverse has not been considered: adding unsmoked tobacco to whiskey to enhance the taste.
Some might think the idea outlandish. However, a drink related to whiskey, as will soon appear, has been paired in this way in Italy. Also, apart from any precedent, on the idea of using a variety of ingredients to make a flavored spirit or a cocktail (lemons, other fruits, mint, cherries, etc.), why not use tobacco? It is another plant or herb-like substance which would seem capable of improving a whiskey or working in a cocktail.
If these considerations aren't enough to persuade, consider that tobacco used to be added to whiskey 100 years ago and more to improve the taste. Some of these concoctions were dubious: the practice clearly in many cases was intended to give a flavor to a white or unrectified new spirit. But the idea of adding tobacco to a good whiskey to make an interesting, fused flavor seems in line broadly with the original practice.
One would need to set aside of course any prejudice against tobacco. I don't smoke but would consider sipping a drink with tobacco infused in it.
Someone in Italy, a craft brewer, has created such a drink, a beer in this case. It is a dark beer flavored with "Kentucky Toscano tobacco".
Intrigued by that phrase, a little research showed that in Italy since the mid-1800's, a reputed cigar has been made called Toscano (it means Tuscan), and the cigar originally was made with flue-cured Kentucky tobacco. Today, that tobacco, albeit in much reduced amount, is still grown and prepared in Kentucky and some other Southern states I believe. Also, that type of tobacco is grown in other countries as well including Italy and parts of Africa. The current Toscano cigar appears (this again from online research) to be made both from imported and domestic examples of this flue-cured leaf.
I think it must be the case that the Italian brewer used a Toscano cigar to get the leaf to add to his beer.
Now, if one had a bottle of any good bourbon and added the same or a different kind of cigar leaf to it, I wonder what the taste would be like?
The Italian beer is called (interestingly) Ke To Re Porter, it is a 5.5% ABV porter and here is the taste note from Eyewitness Companion to Beer, a 2007 book of which Michael Jackson, the late English beer and spirits writer, was editor-in-chief (it appears to be Jackson's last book completed for publication before his untimely death):
"This unusual but pleasant porter is infused with Kentucky Toscano tobacco. Despite strong peppery and smoked flavors, it is surprisngly well-balanced and easy to drink". The brewer is a brewpub called Birra Del Borgo, see www.birradelborgo.it, it is about 60 miles northwest of Rome. I checked the website and there is a page on this beer with a description of its aroma and taste but I can't understand most of the Italian.
I would think any kind of bourbon might be suitable for a whiskey and tobacco-infusion experiment. Something rich and full might be a good place to start. I'm not sure rye would work, although maybe it would, perhaps with certain kinds of pipe tobacco. Bourbon seems a likely candidate though. I think adding something sweet such as corn or another kind of syrup, might be a good idea, too, but maybe not.