Grilled Flatiron Steaks with Tomatoes and Tapenade
['1/3 cup (or more) olive oil', '1/4 cup vegetable oil', '1 cup pitted olives (such as Niçoise or Kalamata), chopped', '1 tablespoon minced capers', '1 garlic clove, minced', '1 anchovy fillet packed in oil, drained, minced (optional)', '2 pounds flatiron, flank, hanger, or skirt steak', 'Kosher salt', 'Zest and juice of 1 orange', '1/4 cup thinly sliced shallots', '2 tablespoons chopped fresh oregano', '2 tablespoons minced garlic', '2 tablespoons smoked paprika', '2 tablespoons vegetable oil', '1 tablespoon crushed red pepper flakes', '4 large tomatoes (about 3 pounds), sliced 1/4" thick', '1 shallot, thinly sliced into rings', '1/4 cup (loosely packed) flat-leaf parsley leaves', '1 tablespoon olive oil plus more for drizzling', 'Flaky sea salt and freshly ground black pepper', '1 bunch watercress, tough stems removed (about 4 cups)', '1 tablespoon fresh lemon juice', 'Ingredient info: Smoked paprika is sold at specialty foods stores and latienda.com.']
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.
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.
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.
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.
Mound watercress on platter. Slice steak against the grain; transfer to platter with tomatoes and watercress. Spoon tapenade on steak and serve alongside.
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