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.

Deglaze the pan by adding wine and scraping the bottom of the skillet to loosen any browned bits. Add tomatoes and oregano, then 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.