Peel the pineapple and score the outside in a diamond pattern.
Place both pineapples in a ziplock storage bag and pour in the Fireball Whiskey. Close the bag and squeeze as much air out as possible. Marinate for at least 2 hours in the refrigerator. Turning half way through.
Prepare rotisserie grill for cooking. On a propane grill set the two outside burners to medium high and the rotisserie burner for medium. Temperature should be about 450⁰.
Combine the raw sugar, brown sugar, and cinnamon in a bowl.
Skewer each pineapple with the rotisserie rod and secure with rotisserie forks.
Apply the sugar mixture to the outside of each pineapple and place the rotisserie rod into the motor on the grill.
Cook for approximately 30 minutes and apply more sugar mixture once the outside looks dry.
Remove the pineapples once the outside is caramelized about 45-60 minutes total cook time.
Carefully slide the pineapples off the skewer and slice into individual pieces for serving.