1. In a large saucepan, heat 2 tablespoons of the oil over moderate heat. Add the garlic and cook, stirring, for 1 minute. Add the tomatoes, oregano sprigs or dried oregano, 1/2 teaspoon of the salt, and 1/4 teaspoon of the pepper. Reduce the heat and simmer, partially covered, until the sauce thickens, about 15 minutes.
2. In a large frying pan, heat the remaining 2 tablespoons oil over moderate heat. Season the steak with the remaining 1/4 teaspoon salt and 1/4 teaspoon pepper. Cook the steak for 5 minutes. Turn and cook until done to your taste, about 5 minutes longer for medium rare. Remove the steak and let rest in a warm spot for 5 minutes. Cut the steak diagonally into thin slices and top with the warm tomato sauce and the chopped fresh oregano, if using.
Wine Recommendation: Barbera--a dry, crisp, medium-bodied red wine from northwestern Italy--is ideal whenever tomatoes and beef come together.