Heat oil in a Dutch oven or large pot. Add meat and brown on all sides. Remove from pan and set aside.
Add onion to pot. Cook until the onions become translucent, about 5 minutes.
Return meat to pot. Add tomatoes, tomato paste, chili powder, salad dressing mix, chilies, kidney beans, cumin and cranberry apple drink. Cover and cook for 1 1/2 hours over medium-low heat, stirring occasionally.
Add pineapple chunks with juice to chili. Break up tomatoes with a fork. Bring to a boil and serve.
Makes 8 servings.