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Preheat grill or cast iron grill pan to medium-high heat. Remove any excess fat from chicken and rinse under cold water. Pat dry with paper towels. Use a pastry brush to brush with olive oil and season with 1 1/2 teaspoons jerk seasoning and salt, if desired. Set aside. Drain pineapple slices and reserve juice. Season both sides of pineapple slices with 1/2 teaspoon of jerk seasoning; set aside. In small saucepan, bring reserved pineapple juice, remaining 1/4 teaspoon jerk seasoning, and brown sugar to a boil over high heat. Reduce liquid by 1/2, about 5 minutes. Remove from heat and set aside.
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