Heat 1 tablespoon of the oil in 12-inch heavy-bottomed nonreactive skillet over medium-high heat. Cooking in batches if necessary to avoid overcrowding, add chops; saute until brown on both sides, 4 to 5 minutes. Remove from pan; set aside.
Pour fat from pan; return pan to medium heat, adding remaining tablespoon of oil. Add onion; saute until softened, about 4 minutes. Add garlic and rosemary; cook until fragrant, about 1 minute longer. Add wine; simmer until reduced by half, scraping browned bits from pan bottom with wooden spoon, 2 to 3 minutes. Stir in tomatoes and olives, then return chops to pan. Reduce heat to low; cover and simmer until chops are cooked through but tender, 15 to 20 minutes.
Transfer chops to each of four plates. Stir parsley into braising liquid; simmer until sauce thickens, 2 to 3 minutes. Adjust seasonings, spoon portion of sauce over each chop, and serve.
Why does the sauce taste sharp and one-dimensional before the meat goes back into the pan? When cooking in a compact kitchen with a standard 12-inch heavy-bottomed nonreactive skillet, managing the moisture balance between fresh aromatics and cured pantry items dictates the final depth of the braise. Fresh rosemary releases volatile aromatic oils immediately upon contact with heat, whereas dried rosemary requires prolonged hydration to soften its needle-like structure. Fresh garlic minced finely will burn within sixty seconds over medium heat, releasing bitter sulfur compounds that ruin the pan fond before the red wine hits the surface. Deglazing requires scraping the bottom vigorously with a wooden spoon while the dry red wine reduces by half, dissolving the caramelized proteins left behind by the browned chops. Canned tomatoes and Kalamata olives introduce distinct chemical profiles: canned fruit provides steady citric acidity, while brined olives contribute concentrated sodium and lactic acid. Substituting brined black olives for Kalamata varieties alters the salt ratio, requiring adjustments to the final seasoning before serving. Round bone arm chops work reliably because their lower collagen content prevents the meat from turning stringy during a rapid 15 to 20 minute simmer on low heat. Finishing the sauce by stirring in fresh minced parsley and simmering for two to three minutes reduces excess water content, concentrating the pan juices into a glossy coating that clings cleanly to the back of a spoon.