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Flank Steak with Bloody Mary Tomato Salad

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by Sara Dickerman

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Ingredients

  • 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)
  • 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

Details

Servings 8
Preparation time 35mins
Cooking time 100mins
Adapted from epicurious.com

Preparation

Step 1

Preparation

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.

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