Prepare the Meat: Season the steaks with a pinch of salt and pepper on both sides.
Sear the Steaks: In a large skillet, heat 1½ tablespoon olive oil over medium heat. Sear the steaks on both sides until browned; 2-3 minutes per side (or to preferred doneness, see notes for times). Remove and set the steaks aside on a plate.
Prepare the Sauce Base: In the same skillet, reduce the heat to medium-low and add the remaining 1/2 tablespoon olive oil. Add the minced garlic and cook for a few seconds until fragrant.
Simmer the Tomatoes: Add the cherry tomatoes and cook until their skins start to wrinkle, about 5 minutes. Pour in the white wine to deglaze the pan, scraping up any brown bits with a wooden spoon. Simmer for 1 minute, until reduced.
Build the Sauce: Add the olives, capers, tomato paste, oregano, and broth. Stir to combine and bring the mixture to a gentle simmer. Cook the sauce for 10 minutes, allowing the flavours to meld and the sauce to thicken slightly.
Finish: Return the steaks to the skillet, nestling them into the sauce. Cook until the steaks are warmed through.
Serve: Transfer the steaks to serving plates and spoon the tomato sauce over them. Garnish with fresh basil leaves or parsley, if desired. Serve hot with crusty bread or a side of pasta.
Steak Doneness Guide:
Instructions for Cooking Thin Cutlets in Sauce:
If using thin cutlets of beef or veal:
Sear the cutlets: Heat olive oil in a large skillet over medium-high heat. Sear the cutlets for 30 seconds to 1 minute on each side until nicely browned. Remove and set aside.
Prepare the Sauce: Make the sauce in the same skillet, following the recipe above. Reduce heat to low, return the cutlets to the skillet, cover, and let simmer until warmed, or until cooked to desired doneness. The goal is to keep the meat tender while allowing the flavors to meld.