A delicious and tender beef braciole filled with prosciutto, breadcrumbs, and parmesan. This meat is braised in a tomato sauce until its tender and the meat falls apart with a fork.
Combine the breadcrumbs, parsley, parmesan, salt, and garlic powder. Then add the olive oil and combine.
Thinly slice the flank steak with a sharp knife into 2 or 3 slices depending on the thickness. Lay the steak flat and use a meat tenderizer to beat the meat until it's flattened and tender. Lay the prosciutto flat on the steak and top with the breadcrumb mixture. Roll the steak up and tie it with butcher string. Season the outside with salt and pepper.
In a large pot add 1 tablespoon of olive oil on medium-high heat. Once the oil is very hot, place the bracioles in the pot to sear. Sear each side for 60-90 seconds. It's good to have all of the braciole in the pot if you can fit them so that there is less steam overcooking the meat. This should be a quick sear. Set them aside.
In the same pot, lower the heat and add olive oil. Then add the garlic and saute for 1-2 minutes. Add the red wine and bring to a simmer. Simmer for 30 seconds. Add the crushed tomatoes, salt, and basil. Bring to a simmer. Add the braciole back to the sauce so that they're almost almost covered with sauce. Cover the pot and simmer low for 3 hours, stirring occasionally.
Remove the braciole and cut the strings off with kitchen shears. Serve over pasta with extra parmesan cheese!
Notes
You want your pot to be very hot when you sear the braciole. I like to use a dutch oven because they heat very evenly. Move quickly when turning the braciole. When you remove the braciole and move onto the sauce, if the pot is burnt at the bottom, you will have to clean it out. If you just have some brown bits, don't worry about cleaning the pot.
When slicing the flank steak, think of it like you're making thinly sliced chicken cutlets. Use a very sharp knife for best results.
Use butcher string and not toothpicks to keep the braciole shut. It will keep it much tighter and result in much more tender meat at the end.