Pineapple-Chile Margarita
['8 (3/4- to 1-inch) chunks peeled pineapple', '4 slices red jalapeño chile with seeds', '1/2 cup 100% blue agave silver tequila', '3 tablespoons fresh lime juice', '3 tablespoons Simple Syrup', '2 tablespoons Cointreau or other orange liqueur', '2 cups ice cubes', 'divided']
Place pineapple chunks and red jalapeño slices in medium bowl. Press firmly on solids with muddler or back of wooden spoon until mashed. Mix in tequila, lime juice, Simple Syrup , and Cointreau, then 1 cup ice. Stir to blend well. Strain into large glass measuring cup. Divide remaining ice between 2 tall glasses. Pour Margarita mixture over.
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