Confidence Man

Confidence Man is a cocktail with attitude and a smooth edge. It’s the kind of drink that doesn’t need to show off, it just works. Whether it’s the boldness of the whiskey, richness from the coffee liqueur, or sharpness from the bitters, this one carries a little mystery and a lot of charm. It’s the type of cocktail you order when you want something strong, but not too heavy. Something with flavor, but not fuss. Confidence Man plays it cool without trying too hard, making it perfect for slow sips, late nights, and conversations that last a little longer than planned.

Tasting Notes

The Confidence Man is bold, smooth, and just a little bit rich. The Kentucky Owl Confiscated bourbon brings deep caramel, oak, and spice right up front. Coffee liqueur adds a touch of sweetness with roasted depth that plays well with the whiskey. The mix of aromatic and orange bitters brings complexity spice from one, citrus from the other without overpowering the drink. It finishes warm, with a slight bittersweet edge that lingers.

Equipment and Glassware

You’ll need a mixing glass, bar spoon, jigger, and a strainer. This drink is stirred, not shaken, to keep the texture smooth and spirit-forward. Serve it in a chilled rocks glass over a large ice cube for slow sipping. A citrus twist, like orange or lemon, makes a great optional garnish to bring out the bitters.

Ingredients

• 2 oz Kentucky Owl Confiscated Bourbon (Purchase Here)
• 0.75 oz coffee liqueur
• 2 dashes aromatic bitters
• 2 dashes orange bitters

Instructions

• Add all ingredients to a mixing glass with ice and stir
• Strain into a chilled coupe glass
• Garnish with flamed orange peel and cherry

Pro Tips

• Use a high-quality coffee liqueur like Mr. Black or St. George for a bolder flavor that won’t overwhelm the bourbon.
• Stir longer than you think—this drink should be cold and slightly diluted for the best balance.
• Expressing an orange peel over the glass adds a nice layer of aroma that complements the bitters.
• If you want to dial back the sweetness, reduce the coffee liqueur slightly or use a less sugary brand.

When to Serve

This Confidence Man cocktail is perfect for after dinner, slow evenings, or anytime you want a smooth, no-fuss drink with a little weight to it. It’s great for cooler nights, late-night conversations, or as a steady sipper when you want something rich without being too heavy. It’s also a nice twist for bourbon lovers who want a break from the usual Old Fashioned.

Which Liquor Brands to Choose

• Kentucky Owl Confiscated is the key—it’s complex and rich enough to hold its own in a stirred drink.
• For coffee liqueur, Gator Bite Coffee Liqueur, St. George NOLA, or even Kahlúa if you want a sweeter finish.
• Use Angostura for aromatic bitters and Regans’ or Fee Brothers for the orange.
• Fresh citrus peel for garnish adds a clean, final touch.

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Confidence Man

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Prep Time: 2 minutes minutes

5 from 1 vote

Course: Drinks

Cuisine: Bourbon, stirred, strong, whiskey

Keyword: Aromatic bitters, Bourbon, bourbon cocktail, coffee liqueur, orange bitters

Servings: 1 drink

Author: Kentucky Owl

Founded in 1879, Kentucky Owl has a long and rich history, just like the finish on this cocktail. It starts old bold and robust with bourbon aged up to 15 years, tempered with a touch of rich, bitter coffee liqueur and a few dashes of bitters to bring it all together.

Ingredients

• 2 oz Kentucky Owl Confiscated Bourbon
• .75 oz coffee liqueur
• 2 dashes aromatic bitters
• 2 dashes orange bitters

See also  Christmas White Russian

Instructions

• – Add all ingredients to a mixing glass with ice and stir
• – Strain into a chilled coupe glass
• – Garnish with flamed orange peel and cherry

Tried this recipe?Leave a comment and let us know how it was!

Enjoy responsibly