Remove steaks from refrigerator. Remove any packaging and let sit at room temperature for at least 30 minutes.

In a large frying pan, sauté shallots in olive oil over low heat for about 15–20 minutes or until golden. Add the diced tomatoes and sauté for an additional 25–30 minutes or until very soft. Add red wine and cook over low to medium heat for five to 10 minutes or until slightly reduced. Add sugar, lemon juice, salt, and pepper. Stir until well combined. Set aside, keeping warm.

To prepare the steaks, drizzle on both sides with one to two tablespoons olive oil and sprinkle with salt and freshly ground black pepper. Preheat oven to 350 degrees Fahrenheit (175 degrees Celsius).

Immediately before serving, preheat a heavy, oven-safe large grill pan over high heat until it’s smoking hot (cast-iron works great here). Add one to two tablespoons olive oil. Add one steak to the grill pan, being careful not to move it once it has been placed in the pan. This will ensure it forms a good crust. Sear the steak for about five minutes on each side.

Transfer the pan to the preheated oven and continue cooking for another seven to nine minutes for medium-rare (130 degrees Fahrenheit/54 degrees Celsius internal temperature) or 10–11 minutes for medium (135 degrees Fahrenheit/57 degrees Celsius internal temperature) doneness. Remove from oven, taking care to use oven mitts, as the handle of the pan will be very hot. Transfer steak to a cutting board and tent loosely with aluminum foil. Let it rest for several minutes before slicing. Repeat with second steak.

While still hot, pour some of the extra pan drippings into the tomato sauce and mix well to combine. Place several spoonfuls of warmed tomato sauce over the steak and serve immediately.