01 -
In a small bowl, combine mayonnaise, ketchup, pickle juice, mustard, Worcestershire sauce, and salt and pepper to taste. Set aside.
02 -
In a large skillet over medium-high heat, cook ground beef until browned and cooked through, about 6 to 8 minutes. Drain well.
03 -
Wipe out the skillet, coat with nonstick spray, and heat over medium heat. Add one tortilla to the skillet. Top half of the tortilla with 1/2 cup cheese, 1/4 of the cooked beef, and pickle slices if using. Sprinkle the other half of the tortilla with 1/2 cup cheese. Fold in half and cook until the cheese is melted and the tortilla is golden brown on one side, about 2 minutes.
04 -
Flip the quesadilla and continue cooking until the cheese is melted and the second side is golden brown. Transfer to a plate and cover to keep warm. Repeat with the remaining tortillas, cheese, beef, and pickles.
05 -
Cut each quesadilla in half. Stack 2 halves on each of the 4 plates.
06 -
Add one wedge of Iceberg lettuce to each plate. Top with shallots and cherry tomatoes. Drizzle both the quesadillas and the salad with the special sauce. Serve more sauce on the side if desired.