It’s really the age old question for bourbon-lovers isn’t it?  On what particular whiskey (or whiskeys) should a whiskey lover spend their hard-earned dollars?  To best answer it, I decided to call in the cavalry.  I contacted a number of bourbon and whiskey bloggers, podcasters, writers, and retailers and asked them to submit their own strategic allocations of a hundred bucks.  The series is called “If I had a Benjamin.” (See the whole series here.)

If I Had a Benjamin

For installment #3, I’ll use a horse racing term, as it’s Derby week, after all (look it up, non-Kentuckians).  You may

remember Chris’s post from Bottom of the Barrel kicking the series off, and now we’re hitting the Exacta with Darren from Bottom of the Barrel as well:

Darren with logo

By Darren, Bottom of the Barrel

First off, when people learn I have a bourbon podcast and blog, they’ll usually ask the polite, “Oh, really, that’s interesting, what’s your favorite bourbon?” A loaded question if there ever was one. I came up with my own standard answer, “It depends on what I’m doing and my mood.” A little dry and not very fun of an answer, but it’s the correct and 100% true answer for myself.

Darren Posing with a ton of Food

Darren from Bottom of the Barrel Posing with a ton of Food

So this question at hand is open ended. It wasn’t “What would you get 1) to bring to a nice dinner party to share, or 2) to a rowdy party, or 3) to give to an old friend…,” so I’ve had to come up with a general answer. I’m going to do my best to choose a number of bottles good for a variety of situations. My portfolio will be diversified so to speak. Essentially, this would be my list to give to intrepid bourbon/whiskey neophytes who want to drop $100 on a good spread, or for myself to have a decent spread on hand at home for any given occasion or mood. I have also limited myself to things readily and easily available year-round at most large liquor stores. So let me get down to it and tell you my choices and why I chose what I did.

Read Darren’s picks on Bottom of the Barrel!


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About Author

Bill is the Co-Founder, Editor-in Chief, and official Bourbon-o-Phile for, and the President and Chief Blending Officer for Four Gate Whiskey Company. He is a native of Louisville, KY in the heart of Bourbon Country. He attended the University of Kentucky in the mid to late 1990s. He has also been published on He has conducted various bourbon and whiskey tastings in cities across the country, and consulted for multiple national labels. He is married with two daughters, and lives in east Louisville. You can follow him on Facebook and Twitter @BillStraub and email him at

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