Time does not include marinating time as it may vary per person. I also have given 2 ways to make this: baking using bone in chicken thighs and for grilling boneless chicken breasts. TIme reflects baking version. Please note cooking times do vary and grilling chicken breasts takes less time.
In a blender add the Marinade/Jerk Sauce ingredients and purée. Add to a large container you can seal. Add the chicken and marinate 2-3 hours in the refrigerator.
Baking
Preheat oven to 400°F. Prior to baking, bring chicken to room temperature. To a large cast iron pan or skillet add oil over medium high heat. Remove chicken from marinade, shaking off excess marinade. Reserve marinade and whisk in the chicken stock and cornstarch, set aside. Sear chicken for about 3-4 minutes on each side or until slightly browned.
Add 3 cups of pineapple chunks over chicken and pour remaining marinade on top. Place skillet in oven and bake, uncovered for 35 minutes. Baste chicken several times. Chicken is done at 165°F. Garnish with green onions.
Grilling:
Heat grill to 400°F. Prior to grilling bring chicken to room temperature. Sprinkle pineapple rings with brown sugar (See Note 2). Clean the grill. Shake off excess marinade from chicken. Reserve marinade and whisk in the cornstarch, set aside. Grill the chicken and pineapple for 4 minutes per side, or until chicken is cooked through depending on thickness (See Notes 4 and 5).
Add the chicken stock and cornstarch to the reserved marinade in a small saucepan. Bring to a simmer and whisk until thickened. Brush grilled chicken with glaze and garnish with green onions.
Notes
Large boneless chicken breasts sliced half horizontally (for Grilling, optional) or chicken thighs bone and skin on (for Baking).
You will need 3 cups of pineapple chunks for baking with chicken and 1 cup for marinade. If using canned you will need 4 cups total. Cut off top and bottom of pineapple, and cut/remove outer skin. Cut fresh pineapple in half vertically and cut out core. slice one half into 1-inch thick pieces. Again you will need 3 cups of pineapple chunks for baking with chicken and 1 cup for marinade. Slice the other pineapple half into 3/4” thick crescent shape slices, sprinkle with brown sugar and grill for 4 minutes on each side.
Of course you can alter the number of peppers for your desired heat. Just use gloves when slicing and wash hands after. The Scotch Bonnet pepper is HOT. Substitute jalapeño peppers if you like less heat.
An inserted meat thermometer should read 165°F when chicken is done.
Turn each piece every 2 minutes slightly 45° to get cross grill marks. Completely optional.