skirt steak with bloody mary tomato salad

INGREDIENTS

• 2 1 1/2 pound skirt steaks
• Kosher salt
• 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