Watermelon Sugar Cocktail
['1 jalapeño, halved lengthwise', '3/4 cup tequila blanco', '2 cups 3/4" cubes seedless watermelon', '6 tablespoons fresh lime juice', '6 tablespoons Simple Syrup', '1/4 cup mezcal or reposado tequila']
Scrape stems, seeds, and veins from jalapeño into a small jar (reserve green flesh for another use). Add tequila; cover and let infuse for 15 minutes. Set a strainer over a small bowl. Pour tequila through strainer and discard solids.
Place watermelon cubes in a large pitcher. Using a muddler or potato masher, coarsely crush watermelon. Stir in lime juice, Simple Syrup, mezcal, and jalapeño tequila. Stir in 2 cups ice. Cover and refrigerate until chilled, about 2 hours.
Fill Old Fashioned glasses with ice. Divide cocktail among glasses and serve.
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