Grilled Flatiron Steaks with Tomatoes and Tapenade

Ingredients

• 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.

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