Arrange tomatoes on a platter in an overlapping single layer; season with salt and pepper.
In a bowl, whisk together pickle brine, lemon juice, Worcestershire, Tabasco, and oil; drizzle evenly over tomatoes.
Top with celery seeds, caraway seeds, horseradish, olives, chives, and dill. Add croutons if using.
Enjoy immediately, or transfer leftovers to an airtight container and refrigerate for up to three days.