Ready in 50 minutes
Depending on the steak�s size, you may have between 8 and 12 pinwheels of stuffed meat at the end of step 2. Freezing the steak for 30 minutes will make butterflying easier. You will need both wooden skewers and twine for this recipe.
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1. Combine garlic, shallot, parsley, sage, and olive oil in small bowl. Following illustrations below, butterfly and pound flank steak into rough rectangle. With steak positioned so that grain runs parallel to edge of counter and opened side faces up, spread herb mixture evenly over surface of steak. Lay prosciutto evenly over steak, leaving 2-inch border along top edge. Cover prosciutto with even layer of cheese, leaving 2-inch border along top edge. Starting from bottom edge and rolling away from you, roll beef into tight log and place on cutting board seam-side down.
2. Starting ? inch from end of rolled steak, evenly space 8 to twelve 14-inch pieces of butcher?s twine at 1-inch intervals underneath steak. Tie middle string first; then working from outermost strings toward center, tightly tie roll and turn tied steak 90 degrees so seam is facing you. Skewer beef directly through outermost flap of steak near seam through each piece of string, allowing skewer to extend ? inch on opposite side. Using chef?s knife, slice roll between pieces of twine into 1-inch-thick pinwheels. Season pinwheels lightly with kosher salt and black pepper.
3. Light large chimney starter nearly full with charcoal (5 quarts, about 80 briquettes); allow to burn until coals are fully ignited and partially covered with thin layer of ash, about 20 minutes. Build modified two-level fire by arranging all coals over half of grill, leaving other half empty. Position cooking grate over coals, cover grill, and heat rack until hot, about 5 minutes; scrape grate clean with grill brush. Dip wad of paper towels in oil; holding wad with tongs, wipe cooking grate. Grill is ready when side with coals is hot (you can hold your hand 5 inches above grate for 2 to 3 seconds).
4. Grill pinwheels directly over hot side of grill until well browned, 3 to 6 minutes. Using tongs, flip pinwheels; grill until second side is well browned, 3 to 5 minutes longer. Transfer pinwheels to cooler side of grill, cover, and continue to cook until center of pinwheels registers 125 degrees on instant-read thermometer, 1 to 4 minutes (slightly thinner pinwheels may not need time on cooler side of grill). Transfer pinwheels to large plate, tent loosely with foil, and let rest 5 minutes. Remove and discard skewers and twine and serve immediately.
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