1 flank steak (about 1 ¾ to 2 lbs)
1/4 cup plus 2 Tbsp. Josh Cabernet Sauvignon, divided
5 garlic cloves chopped (about 2 Tbsp.), divided
1 1/2 tsp. kosher salt
1/4 tsp. black pepper
1/2 cup olive oil
2 cups fresh parsley leaves
1 Tbsp. fresh oregano leaves
1/4 tsp. red chili pepper flakes
Place flank steak in shallow baking dish. Combine 1/4 cup wine and 1 Tbsp. garlic in small bowl. Pour over steak and refrigerate 2 hours. Turn steak, and marinate another 2 hours.
Mix salt and pepper in small bowl.
Combine olive oil, 2 Tbsp. wine, remaining garlic, parsley, oregano, chili flakes, and ½ teaspoon of the salt & pepper mixture in a blender or food processor. Blend, then transfer to a small bowl and refrigerate.
Heat grill to high. Remove steak from marinade and season both sides with salt & pepper mixture. Grill about 4-5 minutes per side depending on thickness of steak, turning once. (The internal temperature in the thickest section of steak is 125°F for medium rare.) Remove steak from grill, cover and let rest 8-10 minutes.
Slice steak and serve with sauce.