For Tomato Juice: 1 lb. ripe tomatoes, chopped 1 green bell pepper, chopped 1 small red chile pepper, such as Fresno, chopped 1 celery stalk, chopped 1/4 c. chopped onion 1 Tbsp. chopped fresh oregano Pinch kosher salt For Cocktail: Freshly ground black pepper, for glass rim Lemon wedge, for glass rim 1 1/2 oz. vodka 3/4 oz. St. Germain Elderflower liqueur 5 oz. homemade tomato juice Celery stick and oregano sprigs, for garnish
Make Tomato Juice: Combine tomatoes, bell pepper, chile pepper, celery, onion, oregano, and salt in a large pot.
Cook over medium-high heat, stirring occasionally, until tomatoes are broken down, 24 to 26 minutes.
Transfer to a blender and puree, then strain through a fine-mesh strainer; discard solids. Chill in an airtight container 1 hour and up to 5 days. (Makes about 2 cups.)
Make Cocktail: Place black pepper on a small plate. Wipe the rim a large glass with lemon wedge and then dip in pepper.
Fill the prepared glass with ice. Add vodka, St. Germain, and tomato juice, and stir to combine. Garnish with celery and oregano.