The Bourbon Cheapskate, Vol. 55: Double-Oaked Challenge Quarterfinals

At this point, the bracket is no longer filled with easy outs, lower-tier bottles or obvious mismatches. Every whiskey still standing has already survived at least one head-to-head matchup, and the field has narrowed to eight bottles that have all earned their place.

The quarterfinal matchups were:

#1 Old Forester 117 Series 1910 Extra Extra Old vs. #9 Bondstone Limited Release Triple Oak

#4 Woodford Reserve Double Oaked vs. #5 Bondstone Heritage Reserve Quad Oak

#2 Woodford Reserve Double Oaked Father’s Day Selection B vs. #10 Bondstone Double Oak Cask Strength

#3 Lucky 7 The Frenchman vs. #6 Old Forester 1910

As before, the whiskeys went blind before the bracket came back into play. I tasted them as AA through HH, scored each individually, then revealed the identities and placed them back into their head-to-head matchups.

Four would survive.

And by the time the round was over, the top of the bracket had been obliterated.

Glass AA

Light mahogany color.

The nose is fragrant, but also warm. Nutmeg, light chocolate, caramel and maybe a hint of tree fruit. It isn’t overwhelming, but it’s inviting.

There’s a strong bit of spice on the front end of the palate — cinnamon, caramel, chocolate, a touch of butter, vanilla and a nice touch of sweetness.

The mouthfeel isn’t greatly oily, but there’s still some creaminess there. The finish lasts nicely, with tart oak, cherries and dark chocolate closing the experience.

This is definitely a strong sipper.

Score: 86.31

Glass BB

Solid mahogany color.

The nose is a little lighter, but still welcoming: buttery toffee, caramel, light nutmeg and whipped cream.

The palate is more defined. There’s spice from both proof and cinnamon, followed by tart red fruit, oak, caramel and a hint of dark chocolate.

The mouthfeel is substantial — rich and oily — and that leads into a finish that is tart, just a little sweet and very delicious.

Oak and tart cherry lead, with a little buttercream and a hint of cinnamon.

Another solid sipper.

Score: 86.58

Glass CC

Light mahogany color.

The nose is again on the lighter side, but filled with friendly and familiar aromas: light toffee, caramel, baking spice and vanilla.

Then the palate takes over.

Dessert in a glass.

Milk chocolate, buttery toffee, light cinnamon, brown sugar and sweet cherries.

The mouthfeel is the best yet — full and creamy — and the finish lasts beautifully as a result.

Chocolate-covered cherries topped with whipped cream.

I want another glass of this later tonight.

Score: 87.13

Glass DD

Rich mahogany color.

The nose steps things up with rich oak, dark chocolate, caramel and nutmeg.

The palate starts sweet, spicy and complex. Brown sugar, toffee, dark chocolate, cherries, cinnamon and light oak all show up.

It isn’t just the flavors. It’s the intensity and the layers.

The mouthfeel is nicely viscous, and the finish is satisfying, with sweet cinnamon, cherries and oak.

This is something that manages to be both enjoyable and challenging to sip.

Score: 87.61

Glass EE

Rich mahogany color.

This has the richest chocolate note on the nose so far. There isn’t a tremendous amount beyond that, although caramel and vanilla begin to show with a little time.

The flavor is absolutely delicious.

Spicy chocolate drizzled with caramel and vanilla, topped with lightly tart cherries and a touch of oak.

The mouthfeel is close to the best of the round, with a creamy base leading into a strong finish of tart cherries, oak, nutmeg and cinnamon.

Another one I want to revisit later.

Score: 87.78

Glass FF

Light mahogany color.

The nose is dark and inviting: rich dark chocolate, caramel, nutmeg, a touch of brown sugar and a hint of oak.

The palate leads with a combination of sweet honey and brown sugar, followed by milk-chocolate-covered cherries, modest baking spice, tart cherry and oak.

I’m really enjoying this one — maybe more than most of the others.

The mouthfeel is nicely creamy, and the finish lasts wonderfully, with tart cherries, dark chocolate and nutmeg.

Score: 87.34

Glass GG

Rich mahogany color.

The nose is potent, including a small blast of ethanol up front, followed by sweet red fruit, savory oak, cardamom and caramel.

The palate is rich and sweet. Spicy cinnamon and brown sugar are muted by tart cherries, cardamom, dark chocolate and a bit of oak.

The mouthfeel is nicely oily, and the finish is more than satisfying — long waves of tart fruit, bittersweet chocolate and muted baking spice.

Another fun dessert dram.

Score: 87.72

Glass HH

Light mahogany color.

The nose is sweet and inviting, although it steps back in the lighter direction: milk chocolate, nutmeg, oak and creamy caramel.

The palate might be the sweetest yet.

Brown sugar and honey lead, followed by sweet cinnamon, cherries, bittersweet chocolate and creamy caramel.

The mouthfeel is lightly oily, and the finish brings cherry SweeTarts, cinnamon and light oak.

Delicious.

Score: 87.02

The Reveal

The quarterfinal glasses were:

AA — Old Forester 117 Series 1910 Extra Extra Old

BB — Lucky 7 The Frenchman

CC — Woodford Reserve Double Oaked Father’s Day Selection B

DD — Bondstone Heritage Reserve Quad Oak

EE — Woodford Reserve Double Oaked

FF — Bondstone Limited Release Triple Oak

GG — Bondstone Double Oak Cask Strength

HH — Old Forester 1910

Now the bracket matters again.

#1 Old Forester 117 Series 1910 Extra Extra Old vs. #9 Bondstone Limited Release Triple Oak

Old Forester 117 Series 1910 Extra Extra Old — 86.31

Bondstone Limited Release Triple Oak — 87.34

The top seed is gone.

Old Forester was very good, with chocolate, caramel, spice, cherries and enough creaminess to make it a satisfying pour.

Bondstone was simply better.

The darker chocolate, cherries, creamy mouthfeel and stronger finish gave the Triple Oak enough separation to pull the upset.

Winner: #9 Bondstone Limited Release Triple Oak

#4 Woodford Reserve Double Oaked vs. #5 Bondstone Heritage Reserve Quad Oak

This was exactly what a quarterfinal matchup should look like.

Woodford Reserve Double Oaked — 87.78

Bondstone Heritage Reserve Quad Oak — 87.61

Two heavy oak treatments. Two rich, dessert-driven profiles. Almost nothing between them.

Bondstone brought dark chocolate, toffee, brown sugar, cherries, spice and layered oak.

Woodford answered with rich chocolate, caramel, vanilla, cherries and a creamy finish.

Seventeen one-hundredths separated them.

Winner: #4 Woodford Reserve Double Oaked

#2 Woodford Reserve Double Oaked Father’s Day Selection B vs. #10 Bondstone Double Oak Cask Strength

Woodford Reserve Double Oaked Father’s Day Selection B — 87.13

Bondstone Double Oak Cask Strength — 87.72

The special Woodford selection delivered exactly what I hoped for: chocolate, buttery toffee, brown sugar, sweet cherries and one of the best mouthfeels of the round.

It still wasn’t enough.

Bondstone Cask Strength brought more intensity, more spice and a long finish filled with tart fruit, bittersweet chocolate and baking spice.

The ten seed takes out the two.

Winner: #10 Bondstone Double Oak Cask Strength

#3 Lucky 7 The Frenchman vs. #6 Old Forester 1910

Lucky 7 The Frenchman — 86.58

Old Forester 1910 — 87.02

Frenchman was rich, oily and flavorful, with buttery toffee, red fruit, oak, caramel and chocolate.

Old Forester 1910 was sweeter and, on this night, just a little more complete.

Brown sugar, honey, cinnamon, cherries, chocolate and creamy caramel gave it the dessert profile I keep rewarding throughout this tournament.

Another top-three seed goes home.

Winner: #6 Old Forester 1910

The Final Four

And just like that, the bracket has been turned upside down.

The #1 seed is gone. The #2 seed is gone. The #3 seed is gone.

The Final Four is:

#9 Bondstone Limited Release Triple Oak

#4 Woodford Reserve Double Oaked

#10 Bondstone Double Oak Cask Strength

#6 Old Forester 1910

The semifinals will be:

#9 Bondstone Limited Release Triple Oak vs. #4 Woodford Reserve Double Oaked

and

#10 Bondstone Double Oak Cask Strength vs. #6 Old Forester 1910

No #1. No #2. No #3. Just four whiskeys that earned their way here blind.

The next post finishes the bracket.

Two semifinals. One championship. One winner.

The Cheapskate Addendum

This is Bourbon Cheapskate, so I should at least acknowledge the obvious problem with this round:

There really aren’t any true cheapskates left.

My usual definition of a Cheapskate bottle is $40 or less. But the larger idea has always been finding something budget-friendly in an increasingly un-budget-friendly whiskey world.

By that broader standard, Bondstone Double Oak Cask Strength deserves some attention.

I paid $47 for it.

That puts it above the official Cheapskate line, but not by much. And in this quarterfinal it won its head-to-head matchup, advanced to the Final Four and posted the best Cheapskate value score of the round at 94.11.

More importantly, it tasted like it belonged with bottles that cost considerably more.

This isn’t a case of saying, “It’s pretty good for the money.”

At $47, Bondstone Double Oak Cask Strength is more than worth having on the shelf. It gives you a higher-proof double-oaked option with rich fruit, chocolate, spice, a substantial mouthfeel and enough intensity to stand up against much more expensive competition.

It may not technically qualify as a Cheapskate bottle.

But it absolutely qualifies as a bargain.

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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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