Grilled Stuffed Flank Steak With Spicy Capicola and Provolone

Imagine a lean, boneless and tender flank steak rolled up into a pinwheel, with rich garlicky Italian meat, cheese, and herbs, on a skewer, grilled to perfection. This grilled stuffed flank steak is just like a giant lollipop! Yes, I’m talking about juicy Italian Meat Lollipops!

Having this blog lets me travel back in time. I can revisit the recipes that we have tried. It has been almost three years ago since David and I made grilled stuffed flank steak. Time sure got away from me. I had big visions and intentions of stuffing other flank steaks with all kinds of things. Somehow I failed to make that happen.

David and I decided to revisit the recipe since it had been so long since we last made the recipe. We needed a tastebud refresher!

This time,  we stuffed the flank steak with an Italian spicy capicola instead of prosciutto. We originally set out to follow the previous recipe. However, we could not get into the parking lot at our regular grocery store! So we abandoned that store and went to another one. We searched the deli counter over and there wasn’t a single slice of prosciutto anywhere.

Perhaps if we had inquired about prosciutto to the deli clerk, she could have helped us. Instead, I found a package of spicy capicola. I couldn’t help but think that that would be a better match for the flank steak. The capicola could really stand up to the beef. Probably even better than the prosciutto. I threw it into the cart as we proceeded to work our way around the store for our other groceries.

Another change to the original recipe was onion powder. I overlooked the shallots when reviewing the recipe and even though David pointed them out at the store, I didn’t realize we needed them. I can vaguely remember the shallots were a little raw and toothy last time. The onion powder provided flavor without the bite. I also grated the garlic and smeared it across the steak, instead of sprinkling it with minced garlic. Overall, these two changes were good ones.

In the words of Bob Ross: “Happy Accidents!”

Since the stuffing ingredients did not require much time to cook, we also grilled the flank steaks just like we would a regular ribeye steak. A good hot sear and fast!

How To Make Grilled Stuffed Flank Steak With Spicy Capicola and Provolone

Using a mallet, place a piece of wax paper over the meat and pound the flank steak into a rough rectangle shape.

Tip: I am here to tell you freezer paper or butcher paper will change your life in the kitchen. I have been using it like crazy lately for anything messy. It catches all the crumbs and creates a clean workspace that you can clean up in seconds, just by balling it up and throwing it into the trash can. I used freezer paper for this job. So much easier! GET A ROLL!

Position the steak so that grain runs parallel to the edge of the counter, season with the salt and pepper, grated garlic, onion powder, and oregano evenly over the surface of the steak. Lay the capicola slices evenly over steak. Leave a 1-inch border along the top edge. Cover capicola with an even layer of cheese, leaving a 1-inch border along the top edge.

Starting from the bottom edge that is closest to the edge of the counter, roll the beef into a tight log and place on cutting board seam-side down.

Tip: Rolling may cause the stuffing to push out as you roll the meat, just push the filling ingredients back inside as you roll the meat. Once the meat is rolled, lay it seam side down onto the work surface. Tie a piece of butcher’s twine around the middle and two ends, to help hold it together, if needed.

Skewer the flank steak:

Evenly space 8 wooden or metal skewers at 1-inch intervals into the steak, starting in the middle working out to about ½-inch from the end of the rolled steak. Skewer the beef directly through the bottom to the outermost flap of steak near the seam, allowing skewer to extend ½-inch on the opposite side. Make sure that both flaps at the seam are skewered and the roll is tight so that the cheese will not ooze out too much when grilling.

Cut the flank steak into pinwheels:

Using a sharp knife, slice the roll between skewers into 1-inch-thick pinwheels. Season the meat lightly with more salt and pepper, if desired.

Light the grill!

Light one chimney full of charcoal. When all the charcoal is lit and covered with gray ash, pour out and spread the coals evenly over half of the coal grate. (If using a gas grill, light half the burners of a gas grill to high heat).

Set cooking grate in place; cover the grill and allow to preheat for 5 minutes.

Clean and oil the grilling grate.

Grill the pinwheels over direct heat undisturbed, until well browned, 3 to 6 minutes. Using tongs, flip the steaks, cover and grill the second side until medium rare, with crisp edges, about 3 to 5 minutes longer.

Transfer the skewered pinwheels to a large serving platter. Let rest at least 5 minutes before serving, or all of those good juices will be on your plate, instead of your mouth!

Serve with or without the skewers.

I served our steaks with some good ole mashed potatoes. You know, there’s just nothing like meat and taters!

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