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Preheat oven to 400°F. Season pork chops on both sides with 1 ¼ tsp. salt and 1 tsp. pepper.
Heat 1 Tbsp. oil in a large skillet over high. Working in batches if needed, sear pork chops until browned, about 2 minutes per side. Transfer chops to a wire rack set inside a rimmed baking sheet; reserve pan drippings in skillet. Roast pork until an instant-read thermometer inserted into the center registers 135°F, about 15 minutes. Let pork rest 5 minutes.
Meanwhile, heat skillet with drippings over medium-high. Add vinegar and cook, scraping up drippings with a wooden spoon. Stir in red pepper flakes, if using, 2 Tbsp. honey, and ¼ tsp. salt. Add grapes, figs, and rosemary and stir to coat. Continue to cook, stirring occasionally, until sauce is thickened and fruit is softened, about 8 minutes. Remove from heat and stir in butter.
Whisk lemon juice, mustard, and remaining 3 Tbsp. oil, 1 tsp. honey, ½ tsp. salt, and ¼ tsp. pepper in a large bowl. Add radicchio and parsley and toss to coat.
Divide radicchio salad and pork chops among plates. Top with agrodolce.