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Mix mustard, mayonnaise, and chopped pickles in a small bowl to combine; season with pepper.
Arrange half of bologna slices in a neat stack. Starting near the center and working toward the edges of the stack, cut four 1"-long slits, spacing evenly. Repeat with remaining bologna.
Heat a dry large skillet, preferably cast iron, over medium-high. Working in batches, arrange bologna slices in a single layer in skillet and cook until browned all over and crisp, about 2 minutes per side. Transfer to a plate as they are done. Save skillet with any fat.
Arrange bread in a single layer in reserved skillet and cook over medium high until golden brown, about 2 minutes per side. Transfer to a cutting board.
To build sandwiches, spread mustard mixture evenly over each slice of bread. Divide bologna between 2 slices and top with lettuce; drizzle with pickle brine. Close up sandwiches and cut in half.