Al Capone Roast


When I was young, my mother used to buy cuts of meat at a butcher shop in the north end of Boston called Al Capone's. That night she would always make her Al Capone Roast. This is a variation of my mothers recipe. Have the butcher run the flank steak through the tenderizer.

Prep Time:
15 mins
Cook Time:
1 hrs
Additional Time:
10 mins
Total Time:
1 hrs 25 mins
6 servings


  • 3 pounds flank steak, pounded thin for easy rolling

  • ¼ cup olive oil

  • 1 (4 ounce) can finely chopped black olives (Optional)

  • 1 cup minced fresh mushrooms (Optional)

  • 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


  1. Preheat the oven to 350 degrees F (175 degrees C).

  2. Rub the flank steak on both sides with olive oil. Sprinkle the mushrooms and olives over the steak, if using. Place a layer of prosciutto, then a layer of mortadella, mozzarella, and then pepperoni. Season with some of the Italian seasoning. Roll the steak up around the filling, and tie with butcher's string. Rub the outside of the roll with remaining Italian seasoning, garlic powder and steak seasoning.

  3. Heat a large cast iron skillet over high heat. Sear the roast over the entire outside. Then leave the roast in the skillet, and place the skillet in the oven.

  4. Roast for 1 hour in the preheated oven, or until the internal temperature reaches 160 degrees F (70 degrees C) when taken in the center of the roast. Let rest for 10 minutes before slicing and serving.

Nutrition Facts (per serving)

554 Calories
38g Fat
4g Carbs
47g Protein
Nutrition Facts
Servings Per Recipe 6
Calories 554
% Daily Value *
Total Fat 38g 49%
Saturated Fat 14g 70%
Cholesterol 113mg 38%
Sodium 1274mg 55%
Total Carbohydrate 4g 2%
Dietary Fiber 1g 4%
Total Sugars 1g
Protein 47g
Vitamin C 1mg 5%
Calcium 416mg 32%
Iron 3mg 19%
Potassium 482mg 10%

* Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs.

** Nutrient information is not available for all ingredients. Amount is based on available nutrient data.

(-) Information is not currently available for this nutrient. If you are following a medically restrictive diet, please consult your doctor or registered dietitian before preparing this recipe for personal consumption.

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