Flank Steak with Bloody Mary Tomato Salad

Name: Flank Steak with Bloody Mary Tomato Salad
Total time: 4 h 50 min
Yield: 6 servings
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

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

Published October 4, 2025

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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.
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.
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.
Mix onion and 1 tablespoon vinegar in a large bowl. Let macerate 10 minutes, tossing often. Add tomatoes, celery, and olives.
10 min
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.
Cut steak crosswise into 1/4"-thick slices. Serve salad with steak.
5 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

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

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

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

10 min

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

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

5 min