Combine 1 cup apple cider, salt, and 3 tablespoons brown sugar in a 2-quart saucepan. Heat and stir until salt and brown sugar are dissolved. Remove from heat. Stir in ice, bourbon, peppercorns, garlic, and bay leaf. Cool brine. Place chops in large resealable plastic bag. Pour brine over chops; seal bag. Refrigerate for 2 to 4 hours.
Preheat oven to 375 degrees. Meanwhile, combine remaining 2 Tbsp. apple cider, 4 Tbsp. brown sugar, and paprika until brown sugar is dissolved. Set aside.
Remove chops from brine; pat dry. Discard brine. Sear both side of chops in an oiled cast Iron pan. Brush with cider/brown sugar glaze. Let rest 5 minutes. Place cast Iron pan in oven for 15 min or until chops are done. (cooking time will depend on thickness of Chops) Garnish with fresh herbs if desired.Adapted from Hy-Vee Seasons July 2020