Grilled Flatiron Steaks with Tomatoes and Tapenade

Ingredients

• •⅓ 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