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Set a fine-mesh strainer over a bowl and add diced tomatoes. Sprinkle liberally with salt and toss to combine. Place onion in a small bowl and pour enough vinegar on top to cover. Let tomatoes and onion stand while you prep the other ingredients.
In a small skillet, cook bacon over medium-high heat, stirring occasionally, until crisped, about 5 minutes. Using a slotted spoon, transfer to a paper towel–lined plate to drain. You should have about 2 tablespoons (30ml) rendered fat in the skillet. Add bread crumbs and cook over medium heat, stirring frequently, until browned and crisp, 3 to 4 minutes. Transfer to a paper towel–lined plate to drain and season liberally with salt and pepper.
Arrange iceberg wedges on plates and spoon dressing over each. Drain quick-pickled onions and sprinkle all over salads, along with drained tomatoes (discard any extracted liquid), bacon, toasted bread crumbs, and chives. Serve.