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When it comes to crafting a memorable evening, few combinations rival the interplay of a robust bourbon and a fine cigar. Today, we’re diving into the dynamic duo of Old Grand-Dad 114 Bourbon and the New World Nicaraguan Oscuro cigar—a pairing that delivers intensity, depth, and a touch of rustic charm. This high-proof bourbon and full-bodied cigar create a sensory experience that’s both bold and balanced, perfect for those crisp fall nights or a reflective moment by the fire.

The Bourbon: Old Grand-Dad 114

Old Grand-Dad 114, a high-rye Kentucky straight bourbon from Jim Beam, is a powerhouse.

ABV: 57% (114 proof)
Mash bill: 63% corn, 27% rye, and 10% malted barley
Nose: The aroma hits with a burst of butterscotch and caramel, laced with cinnamon and rye spice. There’s a subtle smokiness, alongside dark red fruits like plum and a hint of Tootsie Roll sweetness. Oak and a touch of leather round out the bouquet, promising a robust sip.
Palate: The first sip is a spicy, nutty explosion, with rye-driven notes of cinnamon and ginger taking center stage. Caramel and cherry cola provide a sweet counterpoint, while charred oak and dark chocolate add depth. The mouthfeel is surprisingly smooth for its proof, with a warm, tickly heat that invites slow sipping.
Finish: The finish is long and lively, with lingering baking spices, sweet oak, and a touch of molasses. The rye spice fades into a pleasant warmth, making it a bourbon that commands attention without overwhelming.
This bourbon’s high proof and bold flavors make it a versatile mixer, but its complexity shines when sipped neat or with a splash of water, especially alongside a cigar.

The Cigar: New World Nicaraguan Oscuro
The New World Nicaraguan Oscuro, crafted by AJ Fernandez, is a full-bodied cigar known for its rich, dark wrapper and Nicaraguan filler. It’s a favorite among enthusiasts for its bold yet approachable profile, offering a smoky, earthy experience with layers of flavor.

Visual: The Oscuro’s dark, oily wrapper hints at its intensity. It’s well-constructed.
Flavor Profile: cedar and black pepper upfront, followed by cocoa, espresso, and a subtle molasses sweetness. The retrohale reveals earthy leather and a hint of spice, with a creamy texture that lingers on the palate. As the cigar progresses, nutty and roasted notes emerge, complementing its robust foundation.

The Pairing: A Match Made in Smoke and Spice
Pairing Old Grand-Dad 114 with the New World Nicaraguan Oscuro is like orchestrating a duet where both performers shine without stepping on each other’s toes. The bourbon’s high-rye spice and butterscotch sweetness amplify the cigar’s earthy and peppery notes, creating a harmonious balance.

First Act: Start with a sip of Old Grand-Dad 114 neat. The cinnamon and rye spice awaken the palate, preparing it for the cigar’s bold opening of cedar and pepper. The bourbon’s caramel and cherry cola notes enhance the Oscuro’s molasses sweetness, creating a seamless transition from sip to puff.

Midpoint: As the cigar develops its cocoa and espresso flavors, the bourbon’s dark chocolate and charred oak align perfectly, adding depth to the pairing. The Oscuro’s creamy texture softens the bourbon’s heat, making each sip feel smoother and more integrated. A splash of water in the bourbon can open up its fruitier notes, like plum, which pair beautifully with the cigar’s nutty midsection.

Finish: The cigar’s lingering leather and roasted notes dovetail with the bourbon’s sweet oak and molasses finish. The combination leaves a warm, satisfying aftertaste, with the bourbon’s spice complementing the cigar’s earthy close. This pairing is ideal for slow, contemplative evenings, as both the bourbon and cigar reward patience.

Final Verdict
Old Grand-Dad 114 and the New World Nicaraguan Oscuro are a match for those who crave bold, unapologetic flavors. The bourbon’s spicy, high-rye profile and the cigar’s rich, earthy complexity create a pairing that’s greater than the sum of its parts. At under $30 for the bourbon and a comparable price for the cigar, this duo offers exceptional value without sacrificing depth. Whether you’re a seasoned enthusiast or a curious newcomer, this pairing is a must-try for a night of indulgence.
Rating: 88/100 - A robust, flavorful experience that’s both affordable and unforgettable.