When pairing a whiskey and cigar I always base a choice on the whiskey first. A great pairing should allow the whiskey and cigar to shine individually while elevating each other when enjoyed together, but at the very least the cigar should enhance the whiskey.

In this review, we explore the bold Blanton’s Straight From the Barrel paired with the limited-production Oliva Free Will cigar, a dynamic duo that delivers complexity, spice, and depth.

Buy Blanton's Straight from the Barrel

Buy Oliva Free Will

Blanton’s Straight From the Barrel

Blanton’s Straight From the Barrel is a powerhouse bourbon, bottled at full cask strength and known for its layered profile.

• Front Palate: Rich caramel and oak form the foundation.
• Mid Palate: A hint of dark cherry emerges, adding fruit to the depth.
• Finish: Bold baking spices carry the experience through to a long, satisfying close.

It’s a bourbon that combines sweetness, fruit, and spice in a nice balance.

Oliva Free Will Cigar

Oliva’s Free Will is a boutique release with an evolving profile that keeps the smoker engaged from start to finish.

• Opening Notes: Strong pepper blast paired with firm leather undertones.
• Mid-Smoke: Pepper mellows as hints of cocoa and earthiness come forward.
• Overall Character: Bold yet balanced, with a steady backbone that stands up to a high-proof bourbon.

Why They Pair So Well

This pairing thrives on the push-and-pull between strength and refinement:

• The caramel of the Blanton’s tempers the pepper from the Free Will, creating a smoother experience on the palate.
• Interestingly, the bourbon shifts too, its dark caramel transforms into softer vanilla, which allows the dark cherry note to stand out more vividly.

• Returning to the cigar after a sip of Blanton’s, the bourbon’s spice driven finish amplifies the cigar’s spice, bringing forward complexity that might otherwise stay hidden.

The interplay between sweet, spicy, and earthy tones makes this pairing feel alive and constantly evolving.

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Scorecard: Blanton’s Straight From the Barrel & Oliva Free Will

Blanton’s Straight From the Barrel

• Aroma: 8.7/10 – Caramel, oak, and spice-rich nose.
• Palate (Caramel, Oak, Dark Cherry): 9.0/10 – Complex, layered, and bold.

• Finish (Baking Spices): 9.0/10 – Long, warming, and highly satisfying.

Bourbon Average: 9.1/10

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Oliva Free Will Cigar

• Appearance: 8.9/10 – Handsome presentation with solid construction.

• Flavor Complexity: 8.7/10 – Pepper, leather, cocoa, and earth.

• Construction & Burn: 8.9/10 – Steady burn with consistent draw.

Cigar Average: 8.8/10

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Pairing Synergy

• Flavor Harmony: 9.0/10 – Caramel meets pepper beautifully.

• Complementary Contrast: 8.9/10 – Vanilla and cherry against cocoa and earth keep things dynamic.

• Overall Enjoyment: 8.9/10 – Bold but balanced, a pairing that evolves sip to puff.

Pairing Average: 8.9/10

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Final Verdict

8.9/10 – A bold, evolving pairing.
Blanton’s Straight From the Barrel and the Oliva Free Will prove that intensity doesn’t have to mean imbalance. The bourbon smooths the cigar’s pepper while the cigar highlights the whiskey’s spice, resulting in a pairing that’s as dynamic as it is enjoyable. This is a combination worth savoring for those who appreciate strength with refinement.