Combine garlic, shallot, parsley, basil, sage, and olive oil in small bowl.

Slicing horizontally across the steak, butterfly steak into 2 equal rectangles. (While the steak is resting on your cutting board, take your knife and slice it horizontally across the steak, so you end up with 2 halves of the steak).  Our butchers would also be happy to do that for you!  Using a meat mallet, pound flank steak into 2 thin rectangles, each about 10 inches wide.  Position steak so that the grain runs parallel to the edge of the counter, spread herb mixture evenly over surface of steak.

Lay prosciutto evenly over steak, leaving 1-inch border along top edge.

Cover prosciutto with even layer of cheese, leaving 1-inch border along top edge.

Starting from bottom edge and rolling up away from you, towards the top, roll steak into tight log, tucking in any prosciutto or cheese at the top so it’s not hanging over the end.  Place on cutting board seam-side down.

Using a sharp knife, slice roll into 1-inch-thick pinwheels. Season pinwheels with salt and black pepper.

Skewer each pinwheel with a toothpick.

Preheat oven to 350.

Heat a cast iron or ovenproof skillet over medium high heat. Once hot, add a thin layer of olive oil and when oil is hot, place pinwheels in pan, cut side down, and brown for 3 minutes or so. The cheese might make it stick a bit, so use a good flipper!  Turn pinwheels over and place skillet into preheated oven and cook for 5-7 minutes or until steak reaches desired doneness.  If you don’t have an ovenproof skillet, place a rimmed baking sheet in your oven and preheat it to 350, so it gets nice and hot. While it’s preheating, sear your steaks on both sides in a regular skillet. Then place the steak pinwheels on the preheated baking sheet and bake for 5-8 minutes.

Remove from oven, tent with aluminum foil and let rest for 5 minutes.

Bonus – deglaze the pan with some red wine, reduce and serve as an au jus.  Those crispy bits are much too delicious to waste!

Remove toothpicks, if desired,  and enjoy.