- Prepare stuffing: To a medium bowl, add kale and drizzle with 1 tsp oil. Massage oil into kale. Add bread crumbs and parsley and stir to combine. Add egg and stir until mixture starts to clump together. Add peppers, feta and Parmesan, stirring gently to combine. Set mixture aside.
- Butterfly the steak: Place flank steak on a cutting board so that the meat grain is running lengthwise in front of you. Place one hand on top of the meat to hold it in place. Using a sharp knife with a long, thin blade, slowly slice the steak parallel to the board, from one side almost all the way to the other, leaving a 1-inch edge at the uncut side. Open flank steak like a book and sprinkle with 1/4 tsp each salt and pepper. Evenly distribute stuffing over the flank steak, leaving a 1-inch border all around and packing it down with your hands. Starting from the long side, roll up the flank steak, jelly-roll style. Tuck the ends over and tie up the roast once lengthwise using butcher string. Tie the roast crosswise in 4 places. Sprinkle remaining 1/4 tsp each salt and pepper over outside of steak.
- In a large Dutch oven on medium-high, heat remaining 1 tbsp oil. Sear meat, turning occasionally, until browned on all sides, about 8 minutes. To a 5-qt slow cooker, transfer flank steak. To the same pan, reduce heat to medium then add onions and cook, stirring occasionally until softened, 2 to 3 minutes. Add garlic and cook, stirring frequently, until fragrant, about 30 seconds. Add wine, scraping up any browned bits from the bottom of the pan with a wooden spoon. Add puréed tomatoes, basil and oregano and stir to combine. Bring to a boil, reduce heat to low and simmer for 5 minutes. Pour sauce into slow cooker, then cover and cook on low for 3 to 3 1/2 hours until tender but not falling apart.
- Transfer roast from slow cooker to a carving board. Slice into 12 ½-inch-thick slices, removing the butcher twine as you slice. To serve, place 1/3 cup sauce onto each plate and top with 2 slices of roast. Garnish with additional parsley (if using).
- Serving Size 2 slices roast and 1/3 cup sauce
- Calories 346
- Carbohydrate Content 19 g
- Cholesterol Content 117 mg
- Fat Content 15 g
- Fiber Content 4.5 g
- Protein Content 30.5 g
- Saturated Fat Content 6 g
- Sodium Content 457 mg
- Sugar Content 5 g
- Monounsaturated Fat Content 0 g
- Polyunsaturated Fat Content 1 g