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Mash 1 clove garlic with dried oregano, 1/4 teaspoon chile flakes and salt to a paste in a mortar. Stir in 1 tablespoon olive oil and the vinegar. Spread this mixture on both sides of the pork. Set aside. Heat grill. Heat oven to 225 degrees.
Heat remaining oil in a small skillet, add onion and sauté until translucent. Mince remaining garlic and stir in. Add tomatoes, anchovies, remaining chile flakes, olives, capers and raisins. Stir in wine and cook on low until mixture is thick, about 10 minutes. Set aside.
Grill pork close to source of heat, turning once, until nicely browned but not cooked through, about 2 minutes per side. (You can also cook the chops in a grill pan or skillet over high heat for about 2 minutes per side). Transfer pork to a baking dish, slather with tomato mixture and place in oven for 45 minutes for medium, longer for more well done. Arrange pork on a serving platter, spoon any pan juices over it, scatter with oregano and serve.