Flank Steak with Bloody Mary Tomato Salad

Grilled flank steak served with a vibrant Bloody Mary-inspired tomato salad featuring cherry tomatoes, celery, olives, and horseradish in a zesty vinaigrette. Perfect for summer entertaining.

6 servings
4 hr 50 min

Ingredients

  • 2 piece flank steaks
  • 2 teaspoons Kosher salt
  • 2 teaspoons light brown sugar
  • 1 teaspoon paprika
  • ¼ teaspoon cayenne pepper
  • ¼ teaspoon freshly ground black pepper
  • 2 tablespoons vegetable oil
  • 1 cup red onion
  • 3 tablespoons Sherry vinegar
  • 2 pound cherry tomatoes
  • 1 cup celery hearts
  • ½ cup brined green olives
  • 2 tablespoons prepared horseradish
  • 1 tablespoon Worcestershire sauce
  • 1 teaspoon hot pepper sauce
  • ½ teaspoon celery seeds
  • ¼ cup extra-virgin olive oil
  • 1 to taste Kosher salt and black pepper

Cooking Instructions

  1. 1.

    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.

    180 min

  2. 2.

    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.

    85 min

  3. 3.

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

    10 min

  4. 4.

    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.

    10 min

  5. 5.

    Cut steak crosswise into 1/4"-thick slices. Serve salad with steak.

    5 min

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