The Triple Crown Cocktail: A Modern Whiskey Sour Reimagined

A refined balance of bourbon, grapefruit, and amaro creates a smooth, inviting blend.

By Medha deb
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The Triple Crown is a standout contemporary cocktail that fuses bourbon’s smooth warmth with the bittersweet shadows of amaro and the bright complexity of grapefruit liqueur, creating a new classic in the whiskey sour family. Born in Brooklyn and rapidly gaining fans worldwide, this drink balances boldness and approachability—a testament to creative mixology’s exciting possibilities.

Origins and Inspiration: From Ba’sik Bar to Worldwide Fame

The Triple Crown was crafted by Jay Zimmerman at Ba’sik, a respected Williamsburg, Brooklyn cocktail bar. The recipe takes inspiration from Sam Ross’s celebrated Paper Plane (another whiskey-amaro-lemon concoction) but charts its own course with artful ingredient swaps:

  • Pamplemousse (grapefruit liqueur) replaces Aperol, amplifying grapefruit and floral notes.
  • Amaro Montenegro brings citrus, herbal, and subtle bitterness in lieu of more assertive amari.
  • Bourbon remains the backbone, lending vanilla oak and spice.
  • Fresh lemon juice unites the ensemble with bracing acidity.

This compelling combination transforms the foundation of the sour into something nuanced yet crowd-pleasing—a grapefruit whiskey sour with bittersweet depth and delicate complexity.

Ingredient Spotlight: The Pillars of the Triple Crown

Each component of the Triple Crown plays a crucial role, both individually and in harmony with the others. Here’s a closer look at what makes this ingredient roster distinctive:

  • Bourbon Whiskey (1 oz)
    The soul of the cocktail, bourbon delivers sweet vanilla, caramel, and gentle oak. Its mellow but robust spirit binds the diverse flavors together.
  • Pamplemousse (Grapefruit Liqueur, 3/4 oz)
    This citrus-forward liqueur provides vibrant grapefruit notes, mild sweetness, and subtle bitterness—a key twist on the Paper Plane formula. Giffard and St. Elder are popular choices.
  • Amaro Montenegro (3/4 oz)
    An iconic Italian amaro, Montenegro is lighter than some counterparts, with orange, herbs, floral complexity, and hints of spice. It enriches the cocktail’s bittersweet backbone without overwhelming.
  • Fresh Lemon Juice (3/4 oz)
    Brings brightness and balance, offsetting the sweetness and rounding out the cocktail’s profile with snappy acidity.

With all ingredients shaken together, each sip offers waves of citrus, gentle herbal notes, bourbon’s warmth, and a satisfyingly dry finish.

Step-by-Step Recipe: How to Make the Triple Crown

Making the Triple Crown is refreshingly easy—there’s no need for esoteric barware, advanced techniques, or hard-to-source components. Here’s the classic, widely accepted method:

IngredientMeasure
Bourbon whiskey1 oz (30 ml)
Pamplemousse (grapefruit liqueur)3/4 oz (22.5 ml)
Amaro Montenegro3/4 oz (22.5 ml)
Lemon juice (freshly squeezed)3/4 oz (22.5 ml)
  1. Combine all ingredients in a cocktail shaker filled with ice.
  2. Shake vigorously (about 15 seconds) to chill and dilute.
  3. Double strain into a chilled coupe glass.
  4. Garnish with a lemon twist or, for extra flair, a dehydrated grapefruit wheel.

Pro Tip: Freshly squeezed lemon juice is vital for balance and brightness. Using quality bourbon and a good grapefruit liqueur (like Giffard or St. Elder) also elevates the experience.

Tasting Notes: What to Expect

The Triple Crown offers a dance of flavors—each ingredient shining, yet none overpowering:

  • Nose: Inviting aromas of lemon oil and fresh citrus overlay subtle bourbon warmth and herbal tones.
  • Palate: The first sip reveals juicy lemon and grapefruit, quickly joined by a sly herbal bitterness from the amaro and supported by bourbon’s vanilla-spiced backbone. Gentle sweetness rounds things out.
  • Finish: Dry, clean, and slightly tangy, with lingering grapefruit and a touch of anise from the Amaro Montenegro.

This cocktail sits in the sweet spot between refreshment and intrigue: never cloying, never too bitter—just complex enough to reward attention, yet universally appealing to fans of sours or amari alike.

Triple Crown vs. The Paper Plane (and Other Variations)

To fully appreciate the Triple Crown, it helps to compare it with its predecessor, the Paper Plane, and explore a few related variations:

Triple CrownPaper Plane
Bourbon1 oz3/4 oz
Amaro3/4 oz Amaro Montenegro3/4 oz Amaro Nonino
Citrus Liqueur3/4 oz Grapefruit (Pamplemousse) liqueur3/4 oz Aperol
Lemon Juice3/4 oz3/4 oz
ProfileBittersweet, citrus-forward, grapefruit notes, gentler bitternessBittersweet, orange-forward, herbal, slightly sharper bitterness
  • Triple Crown: Broader citrus character, grapefruit complexity, lighter bitterness.
  • Paper Plane: More classic Italian amaro punch, Aperol’s orange and rhubarb, a deeper herbal backbone.

Other variations sometimes appear, such as swapping pamplemousse for other fruit liqueurs, or trying different amari (though Montenegro’s gentle floral bitterness is widely held as ideal for this riff).

Serving Suggestions and Presentation Tips

  • Glassware: Traditionally served in a coupe or Nick & Nora glass for an elegant, classic touch.
  • Garnish: A lemon twist or peel is standard; a dehydrated wheel of grapefruit adds exotic color if available.
  • Ice: None in the glass—shake with plenty of ice, but serve up (without ice) for proper texture.
  • Pairing Notes: Enjoy as a pre-dinner aperitif or as an after-work sipper; its bittersweet profile complements salty snacks, citrus-flavored desserts, and light cheeses.

Nutritional Information

A standard serving of the Triple Crown contains approximately 188 calories, similar to most sours and whiskey highballs. As always, moderation and responsible enjoyment are recommended.

Why the Triple Crown Stands Out

  • Approachable Complexity: Offers a sophisticated flavor journey without intimidating ingredients or proportions.
  • Great Gateway to Amaro: If you’re amaro-curious but haven’t fallen in love with Italian bitters, Triple Crown is a gentle and accessible starting point.
  • Versatile Appeal: Pleases whiskey lovers, citrus-sour fans, and those drawn to herbal liqueurs alike.
  • Visually Appealing: Its sunny straw-gold color and minimalist garnish are inviting and photogenic—ideal for cocktail parties and home bars.

Expert Tips & Troubleshooting

  • Balance your shake: Shake with enough ice and vigor to ensure a frothy, textured pour—but don’t over-dilute.
  • Freshness matters: Use fresh citrus juice and quality liqueurs to avoid muddled or syrupy flavors.
  • Choosing bourbon: A mid-shelf, smooth bourbon (e.g., Woodford Reserve) works well; avoid overly smoky or high-rye variants that could dominate lighter notes.
  • Tasting before serving: Sample a small sip from the shaker to check balance—if it’s too tart, add a dash more liqueur; too sweet, add a touch more lemon juice.

Frequently Asked Questions (FAQs)

Q: Can I substitute the pamplemousse liqueur with fresh grapefruit juice?

A: While fresh grapefruit juice provides bright acidity and citrus flavor, pamplemousse liqueur brings slightly sweet, aromatic grapefruit notes. You can substitute fresh juice in a pinch, but the final cocktail will be drier and less rounded.

Q: What’s the best bourbon for the Triple Crown?

A: A classic, approachable bourbon with vanilla and oak (such as Woodford Reserve, Old Tub Bonded, or Buffalo Trace) is ideal. Avoid overly smoky, peaty, or high-proof bourbons that may overwhelm the other flavors.

Q: Can I try a different amaro instead of Amaro Montenegro?

A: Amaro Montenegro’s light, citrus-forward, floral bitterness is central to the Triple Crown’s balanced charm. Other amari (like Amaro Nonino or Averna) could be swapped in, but expect a deeper, slightly different herbal profile.

Q: Is the cocktail vegan and gluten-free?

A: Yes! If you use vegan, gluten-free bourbon and liqueurs—most major brands are—then the Triple Crown itself contains no animal products or gluten.

Q: How can I batch the Triple Crown for a party?

A: Multiply all ingredients by your desired number of servings; combine bourbon, amaro, and liqueur in advance. Add lemon juice and ice just before serving, shake, and strain. Serve in chilled coupes with fresh garnish for a crowd-friendly version.

Conclusion: The Triple Crown – Instant Classic, Enduring Appeal

The Triple Crown occupies a sweet spot in the modern cocktail canon: it’s rooted in craft tradition but refreshingly innovative; complex enough for enthusiasts, yet easy to love for anyone new to amaro or whiskey sours. Whether you’re aiming to expand your mixology repertoire or seeking a memorable signature drink, the Triple Crown offers flavors as vibrant and layered as its storied Brooklyn origins. Raise a coupe and enjoy the art of the modern whiskey sour reinvented.

Medha Deb is an editor with a master's degree in Applied Linguistics from the University of Hyderabad. She believes that her qualification has helped her develop a deep understanding of language and its application in various contexts.

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