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Kale & Bacon Stuffed Flank Steak with a Red Wine Reduction

Prep Time30 mins
Cook Time25 mins
Total Time55 mins
Servings: 4
Author: Colleen Kennedy


  • Steak
  • 2 - 2 1/2 pound piece of flank steak
  • 1 cup red wine
  • 2 shallots minced
  • 1/4 cup olive oil
  • 8 strips of bacon chopped into 1/2 inch pieces
  • 1 big bunch of kale chopped (about 2 cups after its cooked)
  • 2 TBS red wine vinegar
  • Salt and pepper
  • Red Wine Reduction Sauce
  • 1 TBS olive oil
  • 2 shallots chopped
  • 2 cups of red wine a Cabernet or Merlot work nice
  • 1 TBS honey
  • 1 TBS Worcestershire sauce
  • Salt & pepper


  • Combine red wine, shallots and olive oil and marinate your meat for 4-12 hours, wrapped and in the refrigerator.
  • When ready to cook your meat - remove it from the refrigerator and blot the meat dry.
  • Discard the marinade.
  • Allow the meat to rest on the counter for 30 minutes.
  • Meanwhile, in a large pan with 2 inch deep sides, cook your bacon until crisp.
  • Remove the bacon and leave the drippings,
  • Add in your kale tossing it gently in with the bacon drippings.
  • Saute your kale over medium heat for about 20 minutes or until it is the tenderness you enjoy.
  • Move the kale around often, cover the pan when you can to help it cook quicker.
  • After 12-15 minutes add in a couple splashes of red wine vinegar and season it well. Add in a few TBS of water and cover to continue cooking. Once the kale is done, remove it from the heat, toss in the bacon, adjust seasoning if necessary and when it is cool enough to handle, stuff your flank steak.
  • To stuff your steak - Lay out 6-8 pieces of kitchen twine cut 6 inches in length.
  • Season your meat inside and out with salt and pepper.
  • Lay your meat out and down the middle, pile your kale and bacon filling.
  • Pulling the meat in the middle on either side, wrap it around the filling until the ends overlap and tie it up tight and quick.
  • Work your way out to the ends doing the same thing.
  • The meat is malleable, just work/pull it until you get a good wrap - no filling should be sticking out anywhere except at the very small ends.
  • Make sure you secure each end with the twine.
  • Fire up your grill and cook the meat over medium-high heat for about 8-10 minutes per side or until done to your liking. (Since the beef is tied up and stuffed it will take a bit longer to cook.)
  • Saute the shallots in the olive oil for 2-3 minutes.
  • Add in the wine reduction ingredients, bring to a boil, then reduce by half.
  • Spoon the sauce over the finished meat and serve.
  • Marinade and reduction inspired by Bobby Flay.