FLANK STEAK WITH BLOODY MARY TOMATO SALAD

Flank Steak with Bloody Mary Tomato Salad image

Provided by Sara Dickerman

Yield Makes 8 to 10 servings

Number Of Ingredients 20

Steak:
2 1 1/2 pounds flank steaks
Kosher salt
2 teaspoons (packed) light brown sugar
1 teaspoon paprika
1/4 teaspoon cayenne pepper
1/4 teaspoon freshly ground black pepper
Vegetable oil (for brushing)
Salad:
1 cup finely chopped red onion
3 tablespoons Sherry vinegar, divided
2 pound cherry or grape tomatoes, halved
1 cup chopped celery hearts (inner stalks and leaves; from 1 bunch)
1/2 cup chopped brined green olives plus 2 tablespoons olive brine
2 tablespoons prepared horseradish
1 tablespoon Worcestershire sauce
1 teaspoon hot pepper sauce
1/2 teaspoon celery seeds
1/4 cup extra-virgin olive oil
Kosher salt and freshly ground black pepper

Steps:

For 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.
For 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 1/4"-thick slices. Serve salad with steak.