Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction

Recipe courtesy Bobby Flay

Show: Boy Meets GrillEpisode: Grilling with Wine

Rated: 4 stars out of 5Rate itRead users' reviews (43)

Cook Time:
30 min
Level:
Easy
Yield:
4 to 6 servings

Times:

Prep: 20 min
Inactive Prep: 4 hr 5 min
Cook: 30 min
Total:: 4 hr 55 min

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Ingredients

4 shallots, coarsely chopped
1 cup dry red wine, such as Cabernet
1/4 cup olive oil
2 pounds flank steak, butterfiled
Salt and pepper
1/4-pound thinly sliced prosciutto
1/4-pound thinly sliced fontina cheese
14 fresh basil leaves
Olive oil
Cabernet-Shallot Reduction, recipe follows

Directions

Whisk together shallots, wine and olive oil in a large baking dish. Add the steak and turn to coat. Cover and refrigerate for at least 4 hours or overnight.

Heat grill to high.

Remove the steak from the marinade and blot with paper towels. Lay on a flat surface, cut side up, and season with salt and pepper. Cover the surface with the prosciutto slices, then top with the cheese and a layer of basil leaves. Starting with the side facing you, tightly roll up the steak around the filling. Using kitchen string, tie the roll in 4 or 5 places.

Brush the outside of the steak with oil and season with salt and pepper. Grill the steak over high heat until browned all over, 8 to 10 minutes. Turn the steak 4 times as it cooks. Move the meat away from the direct heat and grill for 15 to 20 minutes, or until an instant-read thermometer registers 125 degrees F for medium-rare. Remove from the grill and let rest 5 minutes before slicing. Slice against the grain into 1/2-inch thick slices and drizzle with the Cabernet-Shallot Reduction.

Cabernet-Shallot Reduction:

2 teaspoons olive oil

3 shallots, finely chopped

1 bottle Cabernet wine

1 teaspoon black peppercorns

Salt

1 tablespoon honey

Heat oil in a large saucepan on the grates of the grill over high heat. Add the shallots and cook until soft. Add the wine and peppercorns, bring to a boil and cook until thickened and reduced to 1 cup. Strain the mixture into a bowl and season with salt, to taste, and honey.

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Comments & Reviews

recipe Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction
Adrian Nashville, TN 08-09-2009
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Followed it to the TEE!! A MAJOR HIT!
Rated: 5 stars out of 5

I read most comments on this recipe and consider myself a seasoned, albeit amateur, chef. I followed this recipe as... described and on another recommendation did not roll the steak and tie it up after stuffing (Which is what Bobby Flay does on the video). You definitely need to let it rest as it really takes in those flavors. Yes, the wine reduction was flavorful but that is expected. Be VERY careful as to which wine you use as they will impart very different flavors on the meat. I used a moderately priced mild cab as recommended. Fresh from the garden basil an excellent smoked prosciutto and the fontina tie together perfectly....I enjoyed mine with corn on the cob, a good french baguette for the reduction and a Presidente pilsner for the southern summer heat. It was a blast!!! My guests really enjoyed it.Read more
recipe Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction
Michael Boise, ID 06-20-2009
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Life of the Party!
Rated: 5 stars out of 5

Excellent! Even for a seasoned palate! Here are my tweeks, ? Red wine & ? Zesty Italian. Caramelize 1 shallot and about ?... pound of mushrooms (dark brown) and use for spread, followed by crispy bacon, fontina, and fresh Basil. I use a little shredded fontina to hold the layers together when cooking. We had a bbq cook off with friends, needless to say I won, thanks Bobby MM Read more
recipe Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction
paula elk grove, CA 05-18-2009
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Excellent choice for birthday BBQ
Rated: 5 stars out of 5

I made this for my sister's 40th birthday a couple of weeks ago and everyone loved it! I followed the recipe as instructed. I... got about 2 1/2 lbs of flank steak from Costco, butterflied it myself (not too bad for my first time), marinated it in a whole bottle of White Oak cab 2004, very smooth with minimal tannins and the shallots. I marinated it for about 7 hours. After I stuffed it, I choose not to roll it based on some of the commments below and as seen in the video he did not roll it either but I used toothpicks to secure the edges which worked perfectly & made it easier for turning the meat. I grilled it for about 10 mins over direct heat on high on the BBQ & kept turning it every 2 mins, then I turned down the flame to low and moved it to indirect heat, closed the lid & cooked it for about 12+ mins & I let it rest before cutting (very important). For the reduction, I used a bottle of Michael David Lodi cab 2005, wines are low in tannins with smooth fruit finish for added sweetness. Remember to always taste the wines before cooking. The adding of honey really helped to smooth out the reduction, it took out the subtle edge that you tasted & I wasn't going to add it at all which I'm now so glad I listened to my mother who said to add it. Moms know best :) To reheat, I wrapped it in foil and put it back on the BBQ on low for about 10-15 mins, the sauce was even more delicious as it had thickened slightly & was more concentrated in flavor. This dish is a keeper & can't wait to make it again. This is really not a difficult dish to make. Bon Apetit Everyone!Read more
recipe Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction
lisa margate, FL 04-17-2009
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Delicious!!
Rated: 5 stars out of 5

Wth a large crowd to feed, I made 2 variations of this recipe. I did the red wine mainade and a second in an Italian dressing... marinade. They were both very delicious! My kids prefered the Italian dressing marinade as I thought they might since the wine is not a taste they're used to. I grilled both steaks for an additional 15 minutes flipping it often so it cooked thru. A very easy yet impressive dish that I will be making again soon! Thanks Bobby!!Read more
recipe Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction
D Franklin, MA 02-02-2009
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This was Delicious and Easy!
Rated: 5 stars out of 5

I love Bobby Flay recipes and this one does not disappoint. I made few changes. Using an 1 1/2 bottles of good red wine for... a steak recipe kills me so I marinated the steak in Italian dressing for a couple of hours, pan seared the steak on all sides and then put the entire pan in a 400 degree oven for 20 minutes(internal temp 130-med rare-med). For the reduction, I made a few changes; I used 2 cups of good red wine, 2 cups of beef broth, garlic and a splash of worcestershire sauce. I've made this 4 or 5 times since November...everyone loves it. Read more
recipe Red Wine Marinated Flank Steak Filled with Prosciutto, Fontina and Basil with Cabernet-Shallot Reduction
Taj Royalston, MA 12-18-2008
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Worked great for me
Rated: 5 stars out of 5

I saw this on a cooking show on a jetBlue flight from Boston to Charlotte, NC, and I decided to look up the recipe online and... cook it for my sister and brother-in-law when I arrived at their house. I've never cooked anything from a cooking show before...I don't think I've ever even cooked a steak on my own in my life. I got a 1.77 lb flank steak from the local Harris Teeter, butterflied it, and marinated it as instructed (although it was already 6pm, so I only marinated it for 2 hours). I drank some Cabernet, a la Bobby Flay, used 1 cup in the marinade and used the rest for the reduction sauce. We didn't have a grill, so I used the broil setting on the electric oven. After stuffing the steak with the prosciutto, fontina, and basil, I put the steak on a cookie sheet (flat, not rolled, like on the tv show) and broiled it for five minutes on each side, then for an additional 2.5 minutes and it was done; a total of about 13 minutes on the broil setting. It turned out perfectly. The steak was tender, and the prosciutto, fontina and basil added wonderful flavor. The reduction sauce added a nice winey sweetness to the dish. I served it with green beans and french bread to soak up the extra sauce. The 1.77 lb steak served three people but could easily serve 4-5 if you serve with additional side dishes. Read more