In the summer, my mother often served this steak with crusty bread and a bowl of her roasted peppers in tomato sauce on the side. Mom made and canned large batches of her peppers in tomato sauce, so the supper took very little time to prepare.
Prepare the tomatoes and bell peppers, working over a bowl to catch all the juices. Cut or tear the peppers into long strips.
Strain all the juices into a large non-reactive saucepan. Add the chili. Bring to a boil over high heat, reduce the heat to medium, and simmer until the juices reduce to a heavy syrup and the chili is very soft, about 10 minutes. Scoop out the chili, seed if desired, and mince.
Add the peppers and tomatoes to the saucepan and bring to a boil. Lower the heat to medium and simmer for 20 minutes. Stir in the chili and salt and pepper to taste. Keep warm or let cool to room temperature.
Prepare the grill and let it burn down to medium coals. Season the flank steak with salt, pepper, 1 teaspoon of the oregano, and brush with 1 tablespoon of the olive oil. Grill, turning once, until done to your taste, about 10 minutes for rare meat (to cook indoors try a cast iron, skillet or bistecca pan). Transfer to a cutting board, drizzle with another 1 tablespoon olive oil, and crumble the remaining 1/2 teaspoon oregano over the top. Let rest for about 5 minutes.
Meanwhile, brush the bread on both sides with olive oil and season with salt and pepper. Grill the bread on both sides until brown and crunchy on the outside but still soft within.
Carve the meat on the diagonal into thin slices and arrange on a platter or plates. Top each slice of grilled bread with about 1/4 cup of the roasted peppers in sauce and arrange next to the meat. (Reserve any remaining peppers for another use.) Gather all the meat juices (make an effort to scrape the meat juices off the carving board, too) into a small bowl and whisk in the vinegar and the remaining 1 tablespoon olive oil. Drizzle over each portion. Serve immediately.
Chef's Note: For fuller flavor, rub the meat with Toasted Spice Rub before grilling.
