Being that AngelsEnvey is the only other "wine cask" finished type bourbon I've had, not drawing from much depth...and I'm just a novice. But, like everyone else, there are certain bourbons I like going back to. This is one of them. Is it worth 40 bucks? MEH, If it wasn't born in Kentucky(my State), at the most award winning Distillery, and if A.Smith Bowman Distillery hadn't done such a fantastic job pointing back to the Bowman Family history and it's ties to early America and Kentucky on their bottles well I probably wouldn't have paid up to try it.(So I'm a sucker for patriotic themes) But I'm glad I did. My only gripe with this Bourbon...it is just too easy to drink. But is that a bad thing? As a fan of Buffalo Trace products, one of my faves is EH Taylor...just the right amount of bite. Issac Bowman is a bit flat on the front. But what it lacks there, it makes up for in flavor. For me there is great balance of the Bourbon and Port. And behind the port I'm tasting Mash Bill #2, and that's Elmer, Blanton's, Rock Hill, Ancient Ancient Age. Nice job A.Smith Bowman. I'd be curious as to what a higher proof would do for this Bourbon?