Place the 3 tomato slices in a mixing glass or cocktail shaker. Add the 0.25 oz red wine vinegar and gently muddle 8–10 times with a muddler or back of a spoon until the tomato breaks down and releases juice but is not a full puree. Aim for a saucy, pulpy texture.

Add 2 oz vodka, 0.5 oz dry vermouth, 0.5 oz fresh lemon juice, 0.5 tsp extra-virgin olive oil, and 1 tsp freshly ground black pepper to the muddled tomato in the shaker.

Shake & Strain

Fill the shaker with ice (about 6 medium cubes). Shake vigorously for 12–15 seconds to chill, dilute, and emulsify the oil into the cocktail so it integrates with the tomato.

Discard ice or water from the chilled glass. Double-strain the cocktail into the chilled coupe or martini glass using a fine mesh strainer in addition to the shaker strainer to remove tomato solids for a smooth, slightly pulpy drink.

Finish & Garnish

Drizzle 1/4 tsp extra-virgin olive oil gently over the surface of the drink.

Place an optional basil leaf and the reserved tomato slice on the rim or floated on the surface. Finish with a light grind of fresh black pepper to taste.

Serve immediately, up (no ice).