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.

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Recipe Summary

prep:
15 mins
cook:
1 hr
additional:
10 mins
total:
1 hr 25 mins
Servings:
6
Yield:
6 servings
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Ingredients

6
Original recipe yields 6 servings
The ingredient list now reflects the servings specified
Ingredient Checklist

Directions

Instructions Checklist
  • Preheat the oven to 350 degrees F (175 degrees C).

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  • 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.

  • 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.

  • 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

554 calories; protein 46.7g; carbohydrates 4.4g; fat 38.2g; cholesterol 113.2mg; sodium 1274.3mg. Full Nutrition
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Reviews (19)

Read More Reviews

Most helpful positive review

Rating: 5 stars
01/25/2004
My husband tried this recipe and it came out delicous. He found it very easy to prepare. Instead of using garlic powder next time he will try fresh garlic. He may also try using hot green olives next time too. The family liked this one very much. Read More
(30)

Most helpful critical review

Rating: 2 stars
01/25/2004
This sounded like it was going to be great but it was just kind of weird. Probably won't make it again. Read More
(39)
25 Ratings
  • 5 star values: 15
  • 4 star values: 3
  • 3 star values: 2
  • 2 star values: 2
  • 1 star values: 3
Rating: 2 stars
01/25/2004
This sounded like it was going to be great but it was just kind of weird. Probably won't make it again. Read More
(39)
Rating: 5 stars
01/25/2004
My husband tried this recipe and it came out delicous. He found it very easy to prepare. Instead of using garlic powder next time he will try fresh garlic. He may also try using hot green olives next time too. The family liked this one very much. Read More
(30)
Rating: 3 stars
01/25/2004
This was ok....I guess it just wasn't for us. All the same....thanks. Read More
(24)
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Rating: 5 stars
11/14/2006
This is excellent and has become a family favorite!! Thanks for sharing! Read More
(22)
Rating: 4 stars
01/03/2006
I'm still new to cooking so this may have beeen a little too tricky for me to attempt. But since my father used to work for Al Capone (the butcher) when he was a young man I had to give it a try. Thanks for the wonderful recipe and memories! Read More
(22)
Rating: 1 stars
02/09/2006
Absolutely gross! Not even fit for the dogs Read More
(20)
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Rating: 5 stars
09/24/2009
My mom shopped in the North End when I was young and would order the pork "Al Capone Special"... it was so sad that they didn't re-open the shop after the fire.. my mom still makes this (from memory) for special occassions... It's a family favorite! Read More
(19)
Rating: 1 stars
04/22/2006
What a terrable thing to do to a flank steak!! It sound good but that is not how it ended up. Tried this again just incase I screwed up..still not good! Read More
(19)
Rating: 4 stars
04/01/2006
The family enjoyed it. Read More
(19)
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