The Bourbon Cheapskate, Vol. 54: Double-Oaked Challenge — Round of 16, Part One

The play-in round is finished. Twenty whiskeys have become 16, and now the bracket starts doing what brackets do.

Win and move on.

Lose and go home.

For the first half of the Round of 16, I poured eight whiskeys blind and labeled them I through P. I knew which bottles were involved, but I didn’t know which glass belonged to which whiskey until every tasting note was finished and every score was locked.

Only then did I reveal the bottles and drop them back into their seeded matchups.

And this round got close. Really close.

Glass I

Rich mahogany color in the glass.

The nose leads with toasted oak, chocolate, cherries and nutmeg, along with a pinch of ethanol. The palate is almost a mirror of the nose, although the ethanol fades and lets the oak, chocolate, toffee and tart cherries come through.

The mouthfeel is nicely creamy. That leads into a pleasant finish of tart oak, tart cherries, toffee and a hint of cinnamon.

Overall, this was a great way to start the round. I’d be surprised if this doesn’t advance.

Score: 85.99

Glass J

The color trends toward light mahogany.

The nose is surprisingly light, or at least lighter than I expected. Even though this seems like a lower-proof whiskey, there’s a hint of ethanol up front before chocolate, nutmeg and cherries follow.

The palate is much stronger. Chocolate, cinnamon, nutmeg, caramel and brown sugar are there in great measure.

The mouthfeel is lightly oily, but the finish is a bit too quick. Even so, it’s still tasty, with chocolate, brown sugar and baking spice dominating.

Overall, this joins the first glass as dessert in a glass.

Easy sipper.

Score: 84.52

Glass K

The color continues the trend of light mahogany.

Oak shows up on the nose in a good way, along with savory baking spice, caramel and vanilla.

The palate opens with red fruit, then brown sugar, caramel and a touch of chocolate. The mouthfeel borders on oily, which helps carry the finish. Cinnamon and toffee linger nicely.

We have another good sipper here and, most likely, a very close result somewhere in this round.

Score: 84.41

Glass L

The color advances to rich mahogany, but whatever oak is here seems to have taken things a little too long — perhaps even to the point of a little bitterness.

Chocolate and baking spice trail some prominent oak on the nose.

The palate amps things up, with nutmeg and toasted oak shining early, followed by plenty of chocolate, brown sugar and a touch of red fruit.

The mouthfeel is surprisingly a bit thin, and the finish is good but not great. Chocolate and baking spice lead oak and brown sugar.

Overall, the color led me to believe this would be better than it was.

It’s good.

But I’m wondering whether it will hold off its competition.

Score: 85.55

Glass M

More beautiful color — once again, solid mahogany.

The nose starts with toasted oak, toasted nuts, dark chocolate and cardamom.

That baking spice continues on the palate, with cardamom and cinnamon arriving early, followed by dark chocolate, oak and citrus.

The mouthfeel is just shy of creamy, but the finish is a pleasant surprise. Toasted oak and chocolate lead the baking spice, and the mixture lingers much longer than expected.

Overall, this isn’t amazing, especially given what I’ve already tasted. It’s not as dessert-forward as I usually prefer.

But it’s still a tasty dram.

Score: 84.47

Glass N

Mahogany is still the color, although a little lighter.

The nose is delicious: rich chocolate, toasted oak, nutmeg and light red fruit.

The palate is just as enjoyable, with sweet cinnamon, brown sugar, dark chocolate, toffee and tart cherries.

The mouthfeel is surprisingly on the thin side, but it’s still OK. The finish is strong, with tart cherries, oak, chocolate and baking spice.

This dram is delicious.

Other than the mouthfeel, this is a contender.

Score: 84.47

Glass O

Solid copper color.

The nose opens sweet with brown sugar, butterscotch, light cinnamon and caramel.

The palate is tasty: light oak and butterscotch, followed by mild cinnamon, caramel and brown sugar.

The mouthfeel is nicely creamy, and the finish is modest but delicious while it lasts — buttery, sweet, lightly spicy with cinnamon and just enough oak.

Overall, this one is simple.

But delicious.

Score: 80.67

Glass P

Like O, we have a solid copper color.

The nose reminds me of kettle corn — buttery, with rich oak, toffee and nutmeg.

The palate is wonderful. Juicy cherries bounce between sweet and tart. The buttery toffee continues, joined by nutmeg, oak and dark chocolate.

The mouthfeel is creamy, and there’s a strong finish with sweet cherries, caramel and light oak.

Overall, it might not be the strongest whiskey in the round, but it’s still a great way to finish the blind.

Score: 84.47

The Reveal

Now comes the fun part.

The glasses were:

I — Bondstone Limited Release Triple Oak
J — Woodford Reserve Double Oaked
K — Death Roll
L — Old Forester 117 Series 1910 Extra Extra Old
M — Lucky 7 Holiday Toast
N — Bondstone Heritage Reserve Quad Oak
O — Forty Creek Copper Pot Reserve
P — Forty Creek 40 Double Barrel Reserve

Now we put them back into the bracket.

#1 Old Forester 117 Series 1910 Extra Extra Old vs. #16 Forty Creek Copper Pot Reserve

Old Forester 117 1910 Extra Extra Old — Glass L — 85.55

Forty Creek Copper Pot Reserve — Glass O — 80.67

This was the least dramatic matchup of the round.

Forty Creek Copper Pot was perfectly pleasant — buttery, sweet and easy-drinking — but Old Forester brought substantially more depth, chocolate, oak and spice.

The mouthfeel wasn’t everything I wanted from the Old Forester, but it didn’t need to be.

The top seed survives.

Winner: #1 Old Forester 117 Series 1910 Extra Extra Old

#4 Woodford Reserve Double Oaked vs. #13 Forty Creek 40 Double Barrel Reserve

Now things get interesting.

Woodford Reserve Double Oaked — Glass J — 84.52

Forty Creek 40 Double Barrel Reserve — Glass P — 84.47

Five one-hundredths of a point.

That’s it.

Forty Creek once again gave me that unmistakable buttery character, this time showing up as kettle corn before cherries, toffee, oak and dark chocolate joined the party.

Woodford went in the more traditional dessert direction with chocolate, caramel, brown sugar and baking spice.

The Forty Creek actually had the better finish.

Woodford had just enough everywhere else.

By the slimmest margin of the round so far, the favorite survives.

Winner: #4 Woodford Reserve Double Oaked

#5 Bondstone Heritage Reserve Quad Oak vs. #12 Death Roll

If the previous matchup was close, this one barely gave me room to breathe.

Bondstone Heritage Reserve Quad Oak — Glass N — 84.47

Death Roll — Glass K — 84.41

Six one-hundredths.

Death Roll brought red fruit, brown sugar, caramel, chocolate and a nicely oily mouthfeel.

Bondstone answered with rich chocolate, toasted oak, sweet cinnamon, brown sugar, toffee and tart cherries. Its weakness was the thinner mouthfeel, but the strong finish helped make up for it.

Death Roll made it interesting.

Bondstone made it through.

Winner: #5 Bondstone Heritage Reserve Quad Oak

#8 Lucky 7 Holiday Toast vs. #9 Bondstone Limited Release Triple Oak

And finally, somebody busted the bracket.

Lucky 7 Holiday Toast — Glass M — 84.47

Bondstone Limited Release Triple Oak — Glass I — 85.99

The Triple Oak was the best whiskey I tasted in this entire group.

Toasted oak, chocolate, cherries, nutmeg, toffee and a creamy mouthfeel all worked together, and the finish kept delivering tart cherry, oak, sweetness and spice.

Holiday Toast was good. In another matchup, 84.47 might have been enough.

Not here.

The first upset of the Round of 16 belongs to the nine seed.

Winner: #9 Bondstone Limited Release Triple Oak

Four Survive

The first half of the Round of 16 is complete.

Moving on to the quarterfinals:

#1 Old Forester 117 Series 1910 Extra Extra Old — 85.55

#4 Woodford Reserve Double Oaked — 84.52

#5 Bondstone Heritage Reserve Quad Oak — 84.47

#9 Bondstone Limited Release Triple Oak — 85.99

Three favorites survive.

One nine seed crashes the party.

And two of the four matchups were decided by a combined eleven one-hundredths of a point.

The other half of the Round of 16 is still waiting.

Eight more whiskeys.

Four more head-to-heads.

And if this half of the bracket is any indication, nobody should feel particularly safe.

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Copyright © 2026 Doug DeBolt.

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About Douglas Blaine

Capnpen is a writer who was a newspaper and magazine journalist in a previous life. A college journalism major, he now works as an English teacher, but gets his writing fix by blogging about a variety of topics, including politics, religion, movies and television. When he's not working or blogging, Capnpen spends time with his family, plays a little golf (badly) and loves to learn about virtually anything.
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