Using a the chef's knife carefully slice directly down the center of the pineapple to separate it into equal 2 inch halves, each half should still have leaves on it after slicing.
Lay each half pineapple (sliced side up) on cutting board exposing the core.
Using the kitchen utility knife, angle the knife tip into the pineapple ¼ inch from the leaves and top and the slice down the right edge of the core to a depth of about 2 inches.
Repeat step 4 on the left side of the core going deep enough so that both cuts intersect in a V under the core.
Cut across the top of the core and the bottom of the core, about ¼ inch from edges so the core is loose.
Lift out the core out and discard.
Cut across and into the pineapple flesh at 1 inch intervals, stopping about ¼ inch from the outside edge and the skin on both sides and the bottom.
Using a spoon, scoop out the 1 inch sections from the pineapple, leaving a hollowed out pineapple cup, reserve these pineapple 'cups' for the cooking/assembly step below.
Cut each of the sections into 1 inch cubes and reserve.
MARINADE
Place the vanilla extract, brown sugar and Three Little Pigs Touch of Cherry BBQ Rub into the large Ziploc bag.
Seal the bag and gently shake to mix the ingredients together and help the sugar to dissolve.
Unseal the bag and add the pineapple chunks* and rum.
Re-seal and let the pineapple to marinate in the refrigerator for 30 minutes.
ASSEMBLY
Pre-heat a covered grill.
Un-seal the Ziploc bag and carefully pour the marinade into the saucepan, reserving the pineapple chunks*
Set the saucepan with the marinade over medium heat, standing well away from the stove top until the rum ignites.
Let the flame die completely before proceeding to the next step.
Stirring as needed simmer the marinade until it is reduced to about ½ a cup.
Lower the heat and reserve, keeping warm.
Remove the pineapple chunks from the bag arrange them in the reserved pineapple halves.
Place the pineapple halves face up on the grill.
Grill pineapples halves on medium heat until the tops of the pineapple chunks start to caramelize.
Transfer the pineapple halves to a serving dish.
Top with the reserved marinade sauce and serve.
Recipe Note
This dish can be served as an interesting side dish or as a dessert with ice cream.
Aluminum saucepans react negatively with vinegar or citrus juices and produce off flavors. Use stainless steel pans or enameled pans wherever possible.
If you want a softer texture you can turn the pieces of pineapple with tongs at mid point during the grilling process.
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