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Recipe Details

Level: Intermediate
Yield: 6 servings
Total Time: 45 min
Active Time: 45 min

Nutritional Analysis Per Serving

Serving Size: 1 of 6 servings

Calories: 641
Total Fat: 40 g
Saturated Fat: 13 g
Carbohydrates: 22 g
Dietary Fiber: 4 g
Sugar: 7 g
Protein: 42 g
Cholesterol: 122 mg
Sodium: 1469 mg

Ingredients

3/4 cup plain breadcrumbs
3/4 cup freshly grated Parmesan, plus more for serving
1/4 cup chopped fresh parsley leaves
2 tablespoons chopped fresh basil, plus 2 whole sprigs of basil
Kosher salt and freshly ground black pepper
7 tablespoons extra-virgin olive oil
5 cloves garlic
1 1/2 pounds beef top sirloin steaks, cut into twelve 1/4-inch-thick slices, then pounded as thin as possible
12 slices prosciutto
3/4 cup red wine, such as Pinot noir
One 28-ounce can crushed tomatoes
1/4 teaspoon crushed red pepper flakes

Special Equipment

Toothpicks

Instructions

In a medium bowl, mix together the breadcrumbs, Parmesan, parsley, chopped basil, and 1/2 teaspoon pepper. In a small bowl, add 4 tablespoons of the olive oil. Grate 3 cloves of garlic into the oil and whisk until blended. Pour the oil mixture into the breadcrumb mixture and stir with a fork until evenly moistened and the texture resembles wet sand.
Place one slice of beef on a clean surface. Lay a slice of prosciutto on top, folding if needed to fit the meat. Spoon 2 tablespoons of the breadcrumb mixture over the prosciutto and press gently to compact. Fold the sides of the beef inward about 1/4 inch. Roll the beef from the bottom, forming a cylinder. Secure the seam with 2 toothpicks. Place the roll on a rimmed baking sheet and repeat with the remaining meat, prosciutto, and breadcrumb mixture. Once all the rolls are ready, season with 1/2 teaspoon salt and 1/2 teaspoon pepper.
Heat the remaining 3 tablespoons of olive oil in a large, deep pan over medium heat. Once the oil shimmers, add the beef rolls in batches, making sure not to overcrowd the pan. Brown each side for about 2 minutes, then transfer to the baking sheet. Repeat with the remaining rolls.
After browning all the rolls, pour the red wine into the pan. Cook, scraping up any browned bits from the bottom, until the alcohol smell dissipates and the wine reduces slightly, about 2 minutes. Add the tomatoes, basil sprigs, red pepper flakes, 1/4 teaspoon salt, and the remaining 2 cloves of garlic. Stir to combine. Pour 1/2 cup water into the empty tomato can, swirl to collect any leftover tomato, and add this liquid to the pan. Bring the sauce to a simmer, then return the beef rolls to the pan. Lower the heat, baste the rolls with the sauce, cover, and cook on low, basting 2 to 3 times during cooking, until the meat is very tender, about 1 hour 45 minutes to 2 hours.
To serve, remove the toothpicks from the rolls and top with sauce and freshly grated Parmesan.