Welcome to the opening round of my 95-and-Under Whiskey Challenge. Over the next two months, 32 whiskeys — all scoring under 95 proof — will face off in a March Madness–style bracket to see which one rises to the top. Each week, I’ll be tasting two blinds of four whiskeys each, with the winners advancing to the Sweet Sixteen, then on to the Elite Eight, Final Four, and the Championship.

🥃 The Contenders

Here’s the full field of 32, seeded from top to bottom:

1. Old Forester 117 Series 1910 Extra Extra Old Bourbon
2. Old Forester 1910 Old Fine Bourbon
3. Barmen 1873 Bourbon
4. Blanton’s Single Barrel
5. Daviess County Medium Toast
6. Russell’s Reserve 10 Year Bourbon
7. Square 6 Kentucky Straight Bourbon High Rye
8. Benchmark Single Barrel
9. Elijah Craig 2025 PGA Championship Edition
10. Weller Special Reserve
11. Angel’s Envy Bourbon Finished in Port Wine Barrels
12. Garrison Brothers Single Barrel Bourbon
13. Eagle Rare 10 Year
14. Jack Daniel’s Distillery Series Finished in Añejo Tequila Barrels
15. Evan Williams Single Barrel
16. Company Distilling Tennessee Whiskey Finished with Apple Wood
17. St. Augustine Florida Straight Bourbon
18. Buffalo Trace Barrel Select
19. Member’s Mark Kentucky Straight Bourbon
20. Sleight of Hand
21. Maker’s Mark
22. Benchmark Small Batch
23. Burlock And Barrel Reserve Whiskey
24. Bowman Brothers Small Batch
25. Evan Williams 1783 Small Batch
26. Bangtail Hoss Original Recipe Whiskey
27. Jim Beam Black 7 Year Kentucky Straight Bourbon
28. Remus Straight Bourbon Whiskey
29. Jack Daniel’s Old No. 7 Tennessee Whiskey
30. Benchmark Top Floor
31. Belle Meade Sour Mash Bourbon
32. Very Old Barton 80 Proof Bourbon

Round One: Blind 1

Matchups:

• (1) Old Forester 117 Series 1910 Extra Extra Old Bourbon vs. (32) Very Old Barton 80 Proof Bourbon
• (16) Company Distilling Tennessee Whiskey Finished with Apple Wood vs. (17) St. Augustine Florida Straight Bourbon

The Pours:

• Glencairn A: Solid copper color. Nose is bready with a hint of leather and vanilla. Caramel appears on the palate, with a creamy mouthfeel and a spicy edge pushing toward an oak-and-caramel finish. Score: 75.5

• Glencairn B: Solid amber. Extremely light nose — bits of vanilla and caramel. Palate opens with apples and cinnamon, a silky smooth mouthfeel, and a cinnamon-led finish. Score: 73.5

• Glencairn C: Dark honey color. Oak dominates the nose, with tree fruit and vanilla in the background. Cinnamon and nutmeg on the palate, thin mouthfeel, and a finish full of oak, vanilla, and spice. Score: 66.7

• Glencairn D: Mahogany in the glass. Stunning nose of brown sugar, plums, cinnamon, and butterscotch. Rich, syrupy palate of cinnamon, caramel, vanilla, and oak. Long, lingering finish with caramel and spice. Score: 87.5

Thoughts About the Blind:
I probably know what each one is — which is the challenge in these early rounds. St. Augustine tends to be oaky, so I suspect that’s A. Very Old Barton is weak on color, which makes me think it’s C. The 117 Series is famous for its dark mahogany color, so that’s likely D, leaving Company as B. But let’s see.

The Reveal:

• Glencairn A: St. Augustine Florida Straight Bourbon

• Glencairn B: Company Distilling Tennessee Whiskey Finished with Apple Wood

• Glencairn C: Very Old Barton 80 Proof Bourbon

• Glencairn D: Old Forester 117 Series 1910 Extra Extra Old Bourbon

Results:

• Old Forester 117 Series 1910 Extra Extra Old Bourbon (87.5) defeats Very Old Barton 80 Proof Bourbon (66.7)

• St. Augustine Florida Straight Bourbon (75.5) defeats Company Distilling Tennessee Whiskey Finished with Apple Wood (73.5)

Advancing: Old Forester 117 Series 1910 Extra Extra Old Bourbon and St. Augustine Florida Straight Bourbon

Round One: Blind 2

Matchups:

• (8) Benchmark Small Batch vs. (25) Evan Williams 1783 Small Batch
• (9) Elijah Craig 2025 PGA Championship Edition vs. (24) Bowman Brothers Small Batch

The Pours:

• Glencairn A: Decent amber. Nose is light — apples, oak, vanilla. Palate brings oak, cinnamon, and vanilla with a modest mouthfeel. Cinnamon and vanilla on the finish. Score: 74.2

• Glencairn B: Light amber. Nose reminds me of A, but less fruity. Palate bursts with cherries and cinnamon, a bit of oak on the back end. Thin mouthfeel, cinnamon-cherry finish. Score: 72.7

• Glencairn C: Deep amber. Nose of warm oak, vanilla, caramel, apples. Palate shows baking spice, vanilla, and butterscotch. Thin-to-silky mouthfeel, lingering spice-vanilla finish. Score: 76.5

• Glencairn D: Solid copper. Nose is lighter — oak, brown sugar, caramel. Palate delivers butterscotch, brown sugar, cinnamon, and oak. Silky mouthfeel, spicy finish with butterscotch hanging on. Score: 76.3

Thoughts About the Blind:
Unlike the first blind, I don’t have a clear idea here. All four were enjoyable, and the differences between them are slim. This one feels wide open.

The Reveal:

• Glencairn A: Bowman Brothers Small Batch

• Glencairn B: Benchmark Small Batch

• Glencairn C: Evan Williams 1783 Small Batch

• Glencairn D: Elijah Craig 2025 PGA Championship Edition

Results:

• Evan Williams 1783 Small Batch (76.5) defeats Benchmark Small Batch (72.7)

• Elijah Craig 2025 PGA Championship Edition (76.3) defeats Bowman Brothers Small Batch (74.2)

Advancing: Evan Williams 1783 Small Batch and Elijah Craig 2025 PGA Championship Edition

Sweet Sixteen So Far

1. Old Forester 117 Series 1910 Extra Extra Old Bourbon
2. Elijah Craig 2025 PGA Championship Edition
3. St. Augustine Florida Straight Bourbon
4. Evan Williams 1783 Small Batch

Coming Next Tuesday

Eight more whiskeys will hit the bracket in Round One, with four more spots in the Sweet Sixteen up for grabs. Heavy hitters like Blanton’s, Barmen 1873, and Russell’s Reserve 10 Year are waiting in the wings.

Stay tuned — the next pour could be a Cinderella story in the making.

Copyright © 2025 Doug DeBolt.