Pineapple-Chile Margarita

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8 (3/4- to 1-inch) chunks peeled pineapple

4 slices red jalapeƱo 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

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