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To prepare the sauce: Chop parsley and garlic together on a cutting board until the parsley is finely minced. Transfer to a medium bowl, add vinegar, oil, 1/2 teaspoon salt and chipotle (or cayenne) pepper; stir to combine.
Preheat grill to high.
To prepare the salad: Combine tomatoes, onion, oil and vinegar in a medium bowl. Season with salt and pepper.
To prepare the steak: Rub steak with oil. Season on both sides with salt and pepper. Grill the steak 3 to 4 minutes per side for medium-rare. Allow the steak to rest 5 minutes; serve with the salad on the side and a dollop of the Chimichurri Sauce on top.