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Al Capone-Inspired Roast from Boston's North End

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PREP TIME
15 min
COOKING TIME
60 min
TOTAL TIME
85 min
SERVINGS
6 servings
Dinner
Al Capone-Inspired Roast from Boston's North End
Ingredients
  • 3 pounds flank steak, pounded thin for easy rolling
  • 1/4 cup olive oil
  • 1 (4 ounce) can finely chopped black olives
  • 1 cup minced fresh mushrooms
  • 8 slices prosciutto
  • 6 slices mortadella
  • 10 slices mozzarella cheese
  • 10 slices pepperoni sausage
  • 1 tablespoon Italian seasoning, divided
  • 1 teaspoon garlic powder, or to taste
  • 1 teaspoon steak seasoning
Instructions
1
Preheat your oven to a medium-high temperature of 350 degrees Fahrenheit or, equivalently, 175 degrees Celsius.
2
Anoint the flank steak with a generous amount of olive oil on both sides, making sure to cover every surface evenly. Add sliced mushrooms and olives to the steak if you're using them, as this will enhance their flavors.
3
Layer sliced prosciutto, mortadella, mozzarella cheese, and pepperoni on top of the steak. Sprinkle some Italian seasoning over this mixture to add depth to your dish.
4
Roll the steak tightly around its filling, securing it with butcher's string. Sprinkle a pinch of remaining Italian seasoning, garlic powder, and steak seasoning over the outside of the roll to add a savory aroma.
5
Heat a large cast iron skillet over extremely high heat until it reaches a scorching temperature. Sear the steak from all sides, making sure to get a nice crust on its exterior.
6
Once you've seared the steak, place it in the skillet and put the skillet directly into the preheated oven.
7
Roast the steak for 1 hour in the oven, or until its internal temperature reaches a safe minimum of 160 degrees Fahrenheit when taken from the center. Remove it from the oven and let it rest for 10 minutes before slicing and serving.