In a medium bowl, combine the bread crumbs, pecorino Romano, ½ cup (20 g) chopped basil, provolone, parsley, 5 minced cloves of garlic, salt, pepper, and the olive oil. Stir and set aside.
Lay the flank steak on a cutting board. Season both sides with salt and pepper. Cover the the meat with a sheet of parchment paper. Using a meat mallet or rolling pin, pound the steak until it’s ¼ inch (6 mm) thick.
Remove the parchment and sprinkle the bread crumb mixture evenly over the steak.
Starting from the bottom, roll the meat into a log. Using butcher’s twine, tie up the roll so it holds its shape while cooking. Season with salt and pepper.
Heat the canola oil in a large Dutch oven over high heat. When the oil is shimmering, add the steak roll and, without moving it, cook until a dark brown crust forms on one side, about 3 minutes. Turn the roll and repeat until all sides and the ends have been seared. Remove the roll from the pan and set aside.
Preheat the oven to 350°F (180°C).
Add the butter, carrot, onion, celery, remaining 3 cloves of garlic, salt, and pepper to the pan and cook until caramelized, about 5 minutes.
Add the white wine and stir to loosen any brown bits from the bottom of the pot. Cook until the wine reduces and the pan is slightly dry again.
Add the tomatoes, bay leaves, oregano, and red pepper flakes. Stir to combine.
Return the beef roll to the pot. Cover and bake for 1 hour, flipping the roll halfway through (if the sauce is drying up too much, add more crushed tomatoes or water), until the beef is tender.
Slice the braciole and arrange on a serving platter with the sauce. Serve the braciole with orecchiette or polenta. Garnish with grated pecorino Romano and fresh basil.
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