Flank Steak With Bloody Mary Tomato Salad

Flank Steak With Bloody Mary Tomato Salad

Ingredients for 8-10 servings

Steak:
¼ teaspoon cayenne pepper
¼ teaspoon freshly ground black pepper
1 teaspoon paprika
2 teaspoons (packed) light brown sugar
2 1 ½ pound flank steaks
Kosher salt
Vegetable oil (for brushing)

Salad:
¼ cup extra-virgin olive oil
½ cup chopped brined green olives plus 2 tablespoons olive brine
½ teaspoon celery seeds
1 cup chopped celery hearts (inner stalks and leaves; from 1 bunch)
1 cup finely chopped red onion
1 tablespoon Worcestershire sauce
1 teaspoons hot pepper sauce
2 pounds cherry or grape tomatoes, halved
2 tablespoons prepared horseradish
3 tablespoons Sherry vinegar, divided
Kosher salt and freshly ground black pepper

Directions

Steak

Place steaks on a large rimmed baking sheet; season with salt. Mix sugar and next 3 ingredients in a small bowl; rub all over steaks. Cover; refrigerate 1-3 hours.

Let steaks stand at room temperature for 1 hour. Build a medium-hot fire in a charcoal grill, or heat a gas grill to high. Brush grates with oil. Grill to desired doneness, about 5-7 minutes per side for medium-rare. Let rest for 10 minutes. DO AHEAD Can be made 1 day ahead. Let cool; cover and chill. Bring to room temperature before slicing.

Salad

Mix onion and 1 tablespoon vinegar in a large bowl. Let macerate 10 minutes, tossing often. Add tomatoes, celery, and olives.

Whisk remaining 2 tablespoon. vinegar, olive brine, horseradish, and next 3 ingredients in a medium bowl. Slowly whisk in oil. Add to bowl with tomato mixture; toss to coat. Season with salt and pepper. DO AHEAD Can be made 4 hours ahead. Cover; chill.

Cut steak crosswise into ¼"-thick slices. Serve salad with steak.

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