Step 1: Cut the steak lengthwise into 2 pieces. Combine 7 tablespoons olive oil, vinegar, wine, 1/4 teaspoon black pepper, and garlic cloves in a medium bowl, stirring with a whisk. Place oil mixture into a large zip-top bag. Add the steak to the bag, press out air, and tightly seal the bag. Turn 3 or 4 times to coat the steaks with the mixture, firmly rubbing the mixture into the steaks. Refrigerate for 4 hours, turning the bag 1 or 2 times while marinating.
Step 2: Heat a large cast iron skillet over medium-high heat. Coat the pan with cooking spray. Remove the steaks from the bag, and discard the marinade. Sprinkle the steaks evenly with 1/2 teaspoon salt. Add the steaks to the skillet and cook 3 1/2 minutes on each side or until desired degree of doneness. Remove from heat. Transfer the steaks to a cutting board; let stand for 5 minutes.
Step 3: While the steaks rest, combine arugula and watercress in a medium bowl. Drizzle with 1 tablespoon olive oil and lemon juice; toss to coat. Divide the dressed greens between 4 plates.
Step 4: Slice the steak diagonally across the grain into thin strips; sprinkle evenly with the remaining 1 tablespoon oil and the remaining 1/4 teaspoon salt. Arrange the steak strips evenly over the arugula mixture on plates. Sprinkle the steak evenly with parsley, chives, and shaved Parmesan. Serve with lemon wedges.
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