I’d go for it. I received a very nice bottle of cognac as a christmas gift a few years back, and it was very much appreciated.
I don’t see a problem with it. I’ve received whiskies before, and they were always welcome because they were something I’d typically not buy for myself. If you think the person would appreciate a bottle of “the good stuff,” I’d say go for it.
In my area of life a classy bottle of liquor probably gets more points than that year’s flashy gadget. Your prospective gift sounds like one of those things that a person might greatly enjoy, but would almost never buy for themselves. Unless they were an alcoholic, but if so I’d expect them to stick to the cheaper liquors that give more quantity. Or if they were a bartender they might appreciate your good eye and thoughtfulness more. If they are neither, but enjoy spirits on occasion, expect the bottle to last a good while with a reminder of you everytime they open it. congodwarf made a great post better than I could put it.
I say go with the gift. Put a neat little bow around it, or put it in a nice box. Presentation’s the only question here. And add me to your Christmas shopping list 
I would support a decision to give Irish whiskey as a Christmas gift. It’s what my own father will get from at least one of his sons this year. I would take a stated preference of one rather high-end whiskey over another as a sign that the fellow has pretty good taste in his daily pour, and probably doesn’t have a drinking problem. A souse would slurp any cheap Canadian blend or American rotgut he could get his hands on.
I recommend Bushmill’s for Irish, Glennfiddich for Scotch. Pricey, but very much worth the extra money.
In a recent thread, someone lamented “Why don’t people give Bailey’s or something?!” I’m with her. If your relative likes Irish Whiskey, give him Irish whisky, especially if it’s the good stuff he wouldn’t usually buy for himself. When I give my friends homemade truffles or cookies, they don’t think I’m commenting on their weight; they think, “Oh, goody”. A voice elsewhere in the room has also suggested your relative might be dropping a hint.
Me, in reaction to the several bottles of scotch and wine we’ve been given and don’t drink (we drink red wine, seldom white, and don’t drink scotch). Not that I don’t appreciate the scotch - the friends who give it to us always have the opportunity to drink it when they visit. But it does seem like when people go buy a “generic bottle” it isn’t necessarily what is drunk in the house it goes to.
I think if you know what someone drinks, and you, yourself, approve of their drinking, giving alcohol is appropriate. If you suspect they do have a drinking problem, it probably isn’t. If you know they are a recovering alcoholic, it never is.
I knew i was someone I liked and respected, and I’ll have you know you inspired me, lady. When it came time to pick a gift for our office Christmas party last week, I saw a Bailey’s flavored hot cocoa set and thought of you. There are also Bailey’s flavored truffles out there!