Begin preheating your grill to medium-high, about 400°F (or preheat a large cast iron skillet over medium-high heat). Use a meat mallet to pound the steak to ¼-inch thickness, then trim the ends square for an even width. Cook up the extra pieces as a snack.
4 pounds skirt steaks
Drizzle the steaks with oil. Mix together the spice blend and salt, then season generously on all sides.
2 tablespoons oil, 4 teaspoons kosher salt, 2 teaspoons black pepper, 2 teaspoons onion powder , 2 teaspoons garlic powder, 2 teaspoons oregano, ½ teaspoon smoked paprika, ½ teaspoon red pepper flakes
Layer the cheese slices over the steak (about 5 per steak), then top with spinach and basil.
15 slices provolone cheese, 1 cup fresh basil leaves, 2 cups fresh spinach
Roll the meat tightly, holding firm so nothing falls out, until you see bits of cheese and green poking out of the spiral. Tie tightly with twine in two places toward the middle, leaving 1 to 1.5 inches between ties, and snip off the excess string. Cut the roll in half between the ties so each half is held in place by twine.
Drizzle the outsides with more oil and season with more salt and pepper on each side. Add to the hot grill, close the lid, and cook about 8 to 9 minutes before flipping for nice grill marks. Flip and continue cooking until a few minutes under your desired temperature. We pulled ours at 120°F (about 20 to 23 minutes total).
1 teaspoon black pepper , 2 teaspoons kosher salt, 2 tablespoons oil
Let the steak rest about 10 minutes, then drizzle with cowboy butter and serve.
Cowboy butter dipping sauce