Preheat oven to 400 degrees F (200 degrees C). Heat the oil in a cast iron skillet over medium-high heat. Brown pork on all sides in the skillet.
Mix the tomatoes, olives, wine, rosemary and garlic in a bowl. Pour over the pork. Season with salt and pepper.
Place skillet with pork in the preheated oven, and bake 30 minutes, to a minimum internal temperature of 145 degrees F (63 degrees C).
Remove pork from skillet, leaving remaining tomato mixture and juices. Place skillet over medium heat, and gradually mix in the cream. Stirring constantly, bring to a boil. Reduce heat to low, and continue cooking 5 minutes, until thickened. Slice pork, and drizzle with the cream sauce to serve.