Note: This is a complex recipe. I recommend separate steps to make it easier. The marinade, pesto stuffing, and demi-glace can be made up to three days ahead and kept in the refrigerator until you put all together, cutting down on the total finish time. The sauce, made a day ahead, can be refrigerated, and gently heated in a double boiler before cooking the flank steak.


3 Lb. Flank Steak, fascia removed with a boning knife
2 Tbsp. fresh basil, chopped
1/3 C. olive oil
3 cloves garlic, chopped
½ C. tomato juice
½ C. red wine
1 bay leaf
2 tsp. black pepper
1 ½ C. bread crumbs
1 C. basil pesto
8 oz. cream cheese, softened
½ C. grated Asiago cheese

Lay flank steak flat on a nap-free, kitchen towel covered, cutting board to secure. A really sharp knife will make this step much easier. With the tip of your boning knife remove the largest sections of fascia on the meat as well as any fat clinging to it. With the steak flat in front of you, cut into it, from the side, grain parallel to your knife. Fold the top back as you go, much like opening a book. Stop before you go all the way through the meat so you have a wide flat surface. Then close your meat “book” for the next step.

Reserving the bay leaf, mix the basil, oil, garlic, tomato juice, wine, and black pepper together in a blender. Pour into a gallon Ziploc bag, add the bay leaf, and carefully place flank steak into it. Make sure marinade is in contact with all of the meat. Lay flat on a sheet pan in the refrigerator for six hours or overnight.

Make the stuffing by combining well, the cream cheese, breadcrumbs, Asiago, and basil pesto. Place in the refrigerator until the flank steak is ready to stuff.  

Pull the flank steak out of the marinade, and pat it dry with paper towels. Open your meat “book” and spread the stuffing all over the surface. But leave about an inch clean all around the edges. Roll up like a jellyroll and tie with cotton butchers twine in several places.   You may want to cut the roll in half so you may handle them more easily in the next step.

Preheat oven to 475º F. Heat a heavy bottomed sauté pan, large enough to hold the rolled flank steak. (Depending on pan sizes available to you, this is why cutting it in half may make it easier.) Pour in1 Tbsp. oive oil for browning the roll on all sides. Place in a roasting pan and cook for 15 – 20 minutes, until a meat thermometer registers 120ºF. Let it set for five minutes after pulling from the oven.

Slice three-quarter inch rounds with a serrated knife and lay the spirals in a fan on top of Sundried Tomato Cream Sauce below.

Serves eight.


2 Tbsp. olive oil
1 French shallot, minced
2Tbsp. garlic, minced
½ tsp. salt
½ tsp. black pepper
1 tsp. dried basil
2 C. red wine – merlot or a soft cabernet
2 C. beef demi-glace*
½ C. heavy cream
2 Tbsp. soaked sundried tomatoes, chopped fine

An hour before making the sauce cover ¼ C. sundried tomatoes with ½ C. boiling water, set aside. Drain well. Finely chop and measure out 2 Tbsp.

Sauté the shallot and garlic until golden, mashing the mixture with the back of a wooden spoon, add salt, pepper, and basil. Pour in one-quarter cup of your red wine to deglaze the pan. Add the rest of the wine and reduce the sauce to one cup, stirring constantly. Add the demi-glace and continue to reduce to about two cups. Add cream and reduce, again, to two cups. Stir in the sun dried tomatoes. When the sauce reaches a boil, remove it from the heat. Makes two cups.

*Four cups of rich beef stock reduced, by heat, to two cups.

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