Mix ground beef and Italian dressing, salt and pepper. Shape into 8 patties. Press pineapple slice into each pattie. Wrap with a slice of bacon and secure with wooden toothpick. Mix remaining ingredients. Place patties in glass 13 x 9 dish. Pour barbecue sauce mix on patties. Cover and refrigerate for 2 hours. Grill patties, pineapple side down, about 10 minutes. Turn, brush with sauce. Grill another 10 minutes. Heat remaining sauce to serve with burgers.
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