- 5 1/3-inch-thick slices of white Pullman bread
- 1 tablespoon plus 1 teaspoon extra-virgin olive oil, plus more for brushing
- 10 pitted prunes
- 1 1/4 cups dry red wine
- 1 piece of pancetta, cut into 1/4-inch dice
- 4 large garlic cloves, very finely chopped
- 4 ounces vacuum-packed cooked chestnuts, coarsely crumbled
- 1 tablespoon chopped rosemary, plus 2 large sprigs
- 1 tablespoon freshly grated pecorino cheese
- 1/4 teaspoon cayenne pepper
- Salt and freshly ground pepper
- 2 large eggs, lightly beaten
- 2 flatiron steaks, each pounded to a 1/3-inch thickness
- 2 1/2 cups beef broth
- 2 large shallots, coarsely chopped
- 2 tablespoons all-purpose flour
How to Make It
Preheat the oven to 400°. Put the bread on a large baking sheet and brush all over with olive oil. Bake for about 20 minutes, until very crisp and golden brown. Let cool. Break up the toasts and transfer to a food processor. Process to coarse crumbs.
In a large glass measuring cup, cover the prunes with 1/2 cup of the wine. Microwave at high power for 1 minute, or until the prunes are soft. Cut the prunes into 1/2-inch pieces and transfer to a large bowl along with the soaking wine.
In a large, deep ovenproof skillet, heat the 1 teaspoon of olive oil. Add one-third of the pancetta and cook over moderate heat until crisp, about 7 minutes. With a slotted spoon, add the pancetta to the prunes. Add the garlic to the skillet and cook over low heat for 1 minute. Scrape the garlic into the bowl. Add the bread crumbs, chestnuts, chopped rosemary, pecorino and cayenne and season with salt and pepper. Stir in the eggs.
Put the steaks on a work surface and season both sides with salt and pepper. Press half of the stuffing over each steak. Roll up the steaks lengthwise and tie at 2-inch intervals with kitchen string.
Turn the oven down to 350°. Heat the remaining 1 tablespoon of olive oil in the skillet until shimmering. Add the steaks and cook over moderately high heat until browned all over, about 8 minutes. Turn the steaks seam side down. Add the remaining 3/4 cup of wine and pancetta to the skillet along with the broth, rosemary sprigs and shallots; bring to a boil. Transfer the skillet to the oven and braise the steaks for about 25 minutes, turning once, until a thermometer inserted in the steaks registers 130° for medium-rare to medium meat.
Transfer the steaks to a carving board to rest for 5 minutes. Whisk the flour into the pan juices and simmer over moderately high heat, whisking a few times, until the gravy is thickened and slightly reduced, about 3 minutes. Strain the gravy into a small saucepan, pressing on the solids. Season with salt and pepper and keep the gravy warm.
Untie the steaks and slice crosswise 1/4 inch thick. Serve with the gravy.