In any case, this has been in my repertoire now for the past five years, and it's definitely become a favorite. I've made it for friends in Marblehead, dinners at my folks' on the Cape, and shared the recipe with friends and $5 Dinner Clubs from San Francisco to New York. I've even had vegetarians tell me, as they smelled the sauce and the steak with the fragrant mint cooking, that they wished they ate meat.
Depending on the time of year, you might not be able to get your hands on fresh mint. Don't worry. Although it doesn't taste quite the same, substituting basil works just fine.
6 tomatoes (loosely cut) Or 1 (28 oz) cans whole peeled tomatoes (loosely cut)
1½ - 2 cups of red wine (nothing fancy)
1½ - 2 T dry oregano
5 cloves garlic (loosely chopped)
Lay your flank steak so that the grain runs horizontally in front of you. Across the middle of it, from left to right, sprinkle your salt and pepper, then your mint, pine nuts, garlic, parsley, Parmesan cheese, and olive oil.
Now comes the "tricky" part - you want to roll it, and then tie it up. Take a piece of string, about 3 feet long, and tie a little loop at one end, and place it aside. Roll the steak forwards, like a burrito or a wrap. As you're rolling it, curl your fingers in, so as to push your filling in, and to make a nice, tight roll. Some of the stuffing may fall out, but it's not the end of the world - you can throw it into the sauce. Once you have your steak rolled, it's time to tie it, to prevent the stuffing from coming out while cooking. Take your string with the loop, and start at one end (I start on the right hand side, which I find easier being right handed). Pull the other end of the string through your loop, and cinch it tight. Keeping the steak flat on your cutting board, just loop the string over and under, over and under, until you reach the opposite end of the steak, and tie it off. Now you're ready to cook.
Put 6 - 8 T of olive oil in a big stockpot, over high heat. You want to brown the steak, searing it. The pot will be hot and spitting, so be careful. It should take about a minute or so per "side". Once the outside of the steak is browned, remove from the pot, and set aside.
Add your tomatoes, garlic, wine, oregano, parsley, and pepper to the pot that still has the oil and bits from the steak, and bring to a simmer. You can also add any of the excess stuffing that fell out when you were rolling the steak. Once the sauce begins to simmer, return your steak to the pot, spooning the sauce over it, making sure that it's mostly covered. When the pot reaches a simmer again, lower the heat to medium-low, cover, and let cook for an hour. Check it about every 10 minutes and spoon the sauce over it, and make sure it's not sticking.
About 20 minutes before the steak is done, put a pot of water on to boil for your pasta. When it boils, throw in your pasta (angel hair is a nice accompaniment, as is penne). This way your pasta should be ready as your steak is. Green beans or asparagus go well with this, so having water boiling for your vegetables around the time that you throw your pasta in will have them coordinated as well.
Once an hour is up, remove the steak from the pot and let it sit for a couple of minutes (keep the sauce on a low heat). Cut the string away, and with a sharp knife, using tongs to hold the steak, cut ¼ inch medallions, and layer them on a plate. A little pasta on the side, some of the sauce poured over the steak and the pasta, and some pine nuts, Parmesan cheese, and parsley sprinkled over the top for garnish, and you're ready to eat.