A darker, more contemplative cousin to the Revolver. Bourbon and coffee remain the backbone, but cacao and amaro add layers that reveal themselves slowly.

Ingredients

• 2 oz bourbon, preferably 90–100 proof
• ½ oz coffee liqueur
• ¼ oz Amaro Averna
• 2 dashes chocolate bitters
• 1 dash orange bitters
• 1 orange peel

Method

1. Add bourbon, coffee liqueur, Averna, and bitters to a mixing glass with ice.
2. Stir for 25–30 seconds.
3. Strain into a chilled Nick & Nora or coupe, served up.
4. Express a broad orange peel over the surface.
5. Briefly flame the orange peel if you're comfortable doing so, then discard it.

What It Tastes Like

The bourbon hits first, followed immediately by roasted coffee. Averna then introduces bitter orange, caramel, herbs, and a faint cola-like quality.

The chocolate bitters aren't there to make it a chocolate cocktail. They deepen the roasted flavors of the coffee, giving the whole drink a dark-cacao finish.

The result lands somewhere between a Revolver, Black Manhattan, and Old Fashioned, without quite being any of them.

I'd keep the coffee liqueur restrained. The danger here is accidentally wandering into espresso-martini country. The Analyst should be dry, dark, and whiskey-forward.

The Concept

Now the three drinks have distinct personalities:

The Case Officer 🥃
Bourbon • Bénédictine • oloroso • chocolate • orange
Warm, personable, layered.
Works the relationship.

The Targeter 🎯
Bourbon • Montenegro • Peychaud's • walnut • absinthe • lemon
Sharp, herbal, precise.
Finds the pattern.

The Analyst 📊
Bourbon • coffee • Averna • cacao • orange
Dark, cerebral, bittersweet.
Explains what it means.

There is also a nice visual progression across a bar: the Case Officer over a large cube, the Targeter neat in an absinthe-rinsed rocks glass, and the Analyst served dark and perfectly clear in stemware. They look related without appearing to be the same cocktail wearing three different name tags.

Glass: Nick & Nora
Strength: Spirit-forward
Profile: Bourbon • roasted coffee • cacao • bitter orange • herbs
Garnish: Expressed/flamed orange peel, discarded
Bourbon: Old Forester 100 would be my first choice here. Its caramel and baking-spice profile has enough muscle to keep the coffee and Averna from commandeering the meeting.