GRILLED FLATIRON STEAKS WITH TOMATOES AND TAPENADE

Grilled Flatiron Steaks with Tomatoes and Tapenade image

Provided by Jeff Carciello

Yield Makes 4 to 6 servings

Number Of Ingredients 26

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)
Steak:
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
Tomatoes:
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.

Steps:

For tapenade:
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.
For steak:
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.
For tomatoes:
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.