
To make the special sauce, in a small bowl, combine mayonnaise, ketchup, pickle juice, mustard, Worcestershire sauce, and salt and pepper to taste. Set aside.
In a large skillet over medium-high heat, cook beef until browned and cooked through, about 6 to 8 minutes. Drain well.
Wipe out skillet, coat with nonstick spray, and heat over medium heat. Working with 1 tortilla at a time, add to skillet. Top half the quesadilla with cheese, beef, and pickles.
Sprinkle top half with cheese. Fold in half and cook until cheese is melted and tortilla is golden brown on one side, about 2 minutes. Flip and cook until melted and golden on the other side.
Transfer to a plate and cover to keep warm. Repeat with remaining tortillas, cheese, beef, and pickles.
Cut each quesadilla in half, and stack halves on each plate.
Add a wedge of Iceberg to each plate and top with tomatoes and shallots. Drizzle with sauce.