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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.
Details
Servings 4
Adapted from epicurious.com
Preparation
Step 1
Preparation
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.
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