Shuck and core the pineapple, retaining the top and bottom for later use. For your final result, it's important that a sturdy cylinder of the fruit remains. Use a long knife to remove the core.
Cut the chicken breast into three equal strips and marinate in a mixture of oil, paprika, cayenne pepper, and salt.
Stuff the marinated chicken strips in the center hole of the pineapple and then season the outside walls with paprika and cayenne pepper.
Wrap the seasoned pineapple in bacon strips. You can affix these with the help of toothpicks. Next, coat the bacon strips with barbecue sauce.
Reaffix the set aside top and bottom to each end of the pineapple and secure with skewers.
Set the fully assembled pineapple on the grill and let it cook for 45 to 60 minutes.
When the juicy grilled pineapple is done, simply cut it into slices and serve. After the fruit has absorbed all that bacon flavor, get ready for an interesting fusion of sweet and smokey! Aloha!