Slice a 2-inch lengthwise slit into the pork chop, opposite the bone. Carefully push the paring knife through the slit & into the center of the pork chop, creating a pocket inside the pork chop. Repeat with remaining pork chops. Wrap each piece of asiago with prosciutto. Gently maneuver a prosciutto-wrapped asiago into the prepared pocket of a pork chop, pushing it as far back as possible such that you can press the incision shut. Repeat with remaining pork chops.
Add the balsamic vinegar, olive oil, maple syrup, mustard, garlic, Italian seasoning. 2 teaspoons kosher salt & ground black pepper as desired to a baking dish or shallow bowl. Stir to combine. Place the stuffed pork chops in the balsamic marinade, turning a few times to ensure they're coated. Set aside for grilling immediately or cover & marinate in the refrigerator for up to 3 days.
Place the pork chops on the grill grates directly over the flame. Grill 3-4 minutes per side, until the pork is nicely charred or an instant-read thermometer inserted in the center of the pork chop registers an internal temperature of 145 degrees F. Transfer the pork chops to a large plate or serving platter. Tent with foil & allow to rest for 3-4 minutes before serving.