- 3 1/2 to 4 pound rump or chuck beef roast
- 1 teaspoon salt plus more to taste
- 1/2 teaspoon freshly ground black pepper
- 1/2 cup extra virgin olive oil
- 1 large carrot, diced (about 1 cup)
- 1 large celery stalk, diced (about 1 cup)
- 1 medium red onion, diced (1 to 1 1/2 cups)
- 2 garlic cloves, finely minced
- 2 Tbsp chopped fresh flat-leaf parsley
- 1 bay leaf
- 1 Tbsp finely chopped fresh sage
- 3 cups medium-bodied Italian red wine (we used a Barbera)
- 1 28-ounce can Italian plum tomatoes, put through a food mill to remove the seeds
- 1 flank steak (3/4 in thick, about 1 1/4 lbs), butterflied
- 2 red bell peppers
- 3 tablespoons chopped parsley
- 6 to 8 thin slices of prosciutto or other cured ham
- 24 medium sized fresh basil leaves
- 2 tablespoons grated Parmesan cheese
- Freshly ground pepper to taste
- 1 bunch watercress for garnish
- Kitchen string
- Trim some of the fat from the meat. Pat dry with paper towels. Season generously with the salt and pepper. Heat the oil in a large, heavy pot or Dutch oven over medium-high heat. When the oil is hot, shimmering but not smoking, add the roast and cook, turning it a few times, until it is nicely browned on all sides, 10-12 minutes. Transfer the meat to a platter.
- Reduce the heat to medium. Add the carrot, celery, and onion. Cook, stirring occasionally until the vegetables are golden brown and begin to stick to the bottom of the pan, 10-12 minutes. Add the garlic, parsley, and sage, and stir until the herbs are lightly colored and fragrant, about 1 minute. Add 1 cup of the wine and stir quickly, lifting up the richly browned caramelized vegetables that stick to the bottom of the pan. When the wine is almost all evaporated and thickly coats the vegetables, return the meat to the pan and turn it over a few times to coat it with the savory base.
- Raise the heat to high, adding the remaining wine, the bay leaf, and the tomatoes, and bring to a boil. Cover the pot, reduce the heat to low, and simmer, turning and basting the meat every half hour or so, until the meat is very tender and flakes away when pierced with a fork, 3-4 hours. Turn off the heat and let the roast sit in its juices for an hour. (You can also put the pot into a 300°F oven and turn the roast every hour.)
- Remove the meat from the pot and place it on a cutting board, covered loosely with aluminum foil. If the sauce is too thin, bring it to a fast boil and reduce it until it has a medium-thick consistency. Taste and adjust seasoning.
- Cut the meat into thick slices (it will probably fall apart), and place on warm serving dishes. Spoon the sauce over the meat and serve hot. Serve with rice, mashed potatoes, or polenta.
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