Season steaks with 1 teaspoon salt and 1/2 teaspoon pepper. Heat 1 tablespoon oil in a large deep skillet over high heat. Add steaks to skillet and cook, undisturbed, until browned about 2 minutes. Flip and cook 1 more minute. Remove steaks from skillet and set aside.
Add remaining oil to skillet and turn heat to medium. Add onions, remaining salt and pepper, and cook, stirring occasionally until softened. Add garlic and cook for 1 minute. Add wine and scrape bottom of skillet to loosen any browned bits. Add tomatoes and oregano and bring mixture to a simmer. Simmer until tomatoes soften, about 5 minutes, stirring occasionally.
Use a potato masher or the back of a spoon to crush the tomatoes. Add in tomato paste and olives and stir to combine. Simmer for 2 minutes.
Return steaks and any juices accumulated to the skillet and cover the steaks in the tomato mixture. Cook until the steak is heated through, 2 to 3 minutes. Remove from heat and add parsley. Serve with crusty bread or over pasta or rice.
