Grilled Flatiron Steaks with Tomatoes and Tapenade

A Mediterranean-inspired grilled steak dish featuring tender flatiron steak marinated in citrus and herbs, served with fresh tomatoes and a rich olive tapenade. Perfect for outdoor grilling and entertaining.

6 servings
1 hr 45 min

Ingredients

  • cup olive oil
  • ¼ cup vegetable oil
  • 1 cup pitted olives
  • 1 tablespoon capers
  • 1 clove garlic
  • 1 fillet anchovy
  • 2 pounds steak
  • to taste kosher salt
  • 1 whole orange
  • ¼ cup shallots
  • 2 tablespoons oregano
  • 2 tablespoons garlic
  • 2 tablespoons smoked paprika
  • 2 tablespoons vegetable oil
  • 1 tablespoon red pepper flakes
  • 4 whole tomatoes
  • 1 whole shallot
  • ¼ cup parsley
  • 1 tablespoon olive oil
  • to taste sea salt and black pepper
  • 1 bunch watercress
  • 1 tablespoon lemon juice
  • ingredient info

Cooking Instructions

  1. 1.

    Stir 1/3 cup olive oil, next 4 ingredients, and anchovy, if using, in a small bowl. Add more olive oil for a thinner tapenade, if desired. (For a smoother sauce, purée tapenade in a food processor or blender.) Set aside.

    10 min

  2. 2.

    Place steak in a large baking dish and season generously with salt. Stir orange zest and juice and remaining 6 ingredients in a small bowl to combine. Spread mixture evenly over both sides of steak and let marinate at room temperature for 1 hour.

    60 min

  3. 3.

    Build a medium-hot fire in a charcoal grill, or heat a gas grill to high. Grill steak, turning once, until nicely charred, about 5 minutes on each side for medium-rare. Transfer to a carving board and let rest for 5-10 minutes.

    20 min

  4. 4.

    Arrange tomatoes on a serving platter. Scatter shallot and parsley over; drizzle with oil and season with salt and pepper. In a medium bowl, toss watercress with 1 tablespoon each oil and lemon juice. Season watercress to taste with salt.

    10 min

  5. 5.

    Mound watercress on platter. Slice steak against the grain; transfer to platter with tomatoes and watercress. Spoon tapenade on steak and serve alongside.

    5 min

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