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


So we’re winding down the “If I had a Benjamin” series. It’s been a lot of fun to read how all these other writers would spend their Benjamins, and equally fun to see the diversity of tastes between so many colleagues I regularly read and admire. So thanks to Gary and all the other bloggers, writers, podcasters, and fans I’ve affectionately dubbed the “Bourbon Brain Trust” who have chimed in.

I get to post mine last. Why? Because I organized this whole thing and that’s my prerogative.  Woo!

Bill 4.0If I Had a Benjamin…

By Bill Straub,


I wrote from the perspective of “my house burned down, and I need bourbon to drink while I wait on an insurance check that might be months in the making, and I have only $100 to buy it.” This is what I’d want on hand for an undetermined amount of time to get me through the long, cold nights in a hotel or a friend or relative’s guest room.

So here it is:

If I had a Benjamin List 1

I’d want both tasty bourbons, and enough variety in style to keep me from getting bored. So bourbon #1 is Old Weller Antique. I’ve never been a huge fan of younger wheaters, but the Old Weller Antique has grown on me immensely of late. It’s soft, sweet, and packs enough heat at 107 proof to be the most interesting of the regular production and mostly attainable wheated bourbons on the market, edging out Makers 46, Larceny, and Old Fitz Bonded for that honor. And at $25, it’s a good value pick for my Benjamin that I plan to stretch very thin.

Pick #2 is an attempt to get a very woody and oaky bourbon into the mix. Heaven Hill 6 year Bottled-in-Bond does that at an insanely low cost (around $13). This isn’t widely distributed outside of the Kentucky area, but it’s fairly easy to obtain in Louisville, and it’s a regular on my bar. It’s sweet, but has a very smooth oaky finish that many older bourbons can’t match. And it’s possibly the best value in bourbon today.

Pick #3 is the one I’d reach for most often on a regular basis, and that’s Colonel E. H. Taylor Small Batch. It borders on busting my budget at $39, but it’s the quintessential Buffalo trace flavor profile, which I absolutely love, with well-balanced flavors and a clean, crisp finish that really delivers. It would be my premium pick of the lot.

And Pick #4 would be Old Forester Signature. I challenge anyone to find a more flavorful 100 proof bourbon at $22 or under. It’s at once a great sipper and a great mixer, with super clean flavors and a dry, clear finish.

There it is. That’s my super list.  Thoughts?

But wait! Don’t click the “X” in the right corner yet, I’m not done. Like post #1 in the series, I’m also coming up with a second list.  Again, this is my site, and this series was my idea, so I’m running with it.

I had two thoughts when determining my allocations, and the second list is based on trying to get the widest variety using “good” whiskey for the least cost. So if I had $100, and wanted to stock a lot of good juice with a lot of variety, this is what I’d do. This sort of became my “all-value/max-variety” list.

If I had a Benjamin List 2

#1 is the aforementioned Heaven Hill 6 Year Bottled-in-Bond. Again, the value can’t be beat.

For the second bottle, I’d try to get a wheated bourbon. But while Old Weller Antique might be a slightly better tasting bottle, it’s not as fiscally thrifty as Old Fitzgerald Bottled-in-Bond. Old Fitz Bonded is the younger, higher proof expression of Larceny. It’s also a fraction of the cost of most other decent wheated bourbons, at only $16. It’s sweet, with plenty of heat, and easily slides into the wheater space on the list.

I’d also want a high rye option, and that means Old Grand-Dad Bottled-in-Bond is the only logical choice. It’s around $14, shares a mash bill with its older cousin, Basil Hayden’s, and provides a spiciness that is hard to find in other recipes, particularly at this price point.

But a high rye bourbon isn’t the only answer to getting that spicy rye and citrus character. I’d also throw in a bottle of Rittenhouse Rye Bottled-in-Bond. 100 proof rye at 30 bucks is a good deal, especially when it’s as smooth and well-balanced as Rittenhouse.

To round out the list at a liver-pounding 5 bottles of whiskey would be a complete 180 from the Rittenhouse, and it would be a Wheat Whiskey. Bernheim Wheat Whiskey is 7 years old, sweet, makes great cocktails, is an awesome summer sipper, and a great juxtaposition to the spiciness of the higher rye selections. I can also find it for $26.

A quick calculator exercise later and I see that my list #2 comes out to a cool $99, leaving me a crisp dollar bill to pocket, and rounding out the contributions for If I had a Benjamin. I don’t suppose there would be much interest in an “If I had a Washington” series, huh?  Oh well.

We’ll take a look at the all submissions throughout the next week and have some follow up commentary, so stay tuned to for the If I had a Benjamin post-script!  Also, go vote for your favorite submission now!


First List:

Second List:

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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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