Skirt Steak With Bloody Mary Tomato Salad

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4 teaspoons (packed) brown sugar, light or dark

2 teaspoons paprika

1/2 teaspoon cayenne pepper, or to taste

1/2 teaspoon freshly ground black pepper

Vegetable oil (for brushing)

1 cup finely chopped red onion

3 tablespoons Sherry vinegar, divided

2 pounds cherry or grape tomatoes, halved (from about 3 pints or 10 ounce containers)

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

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