Using a large serving bowl, layer 3 cups of the chopped lettuce, ½ cup of the black olives, ½ cup of the sliced red onion, ½ of the sliced tomatoes, and ½ cup of the croutons.
Layer the remaining lettuce, black olives, sliced red onion, sliced tomatoes, and croutons.
Lay the pepperoncini peppers on top of the salad.
Evenly sprinkle the grated parmesan on top of the salad. Set the salad aside.
Using either a small mixing bowl and a whisk, or a quart-sized mason jar with a lid, combine the olive oil, white wine vinegar, water, mayonnaise, sugar, fresh minced garlic, lemon juice, Italian seasoning, kosher salt, black pepper and red pepper flakes. If using the bowl and whisk, whisk until the dressing is well combined. If using the mason jar, tightly screw on the lid and shake until the ingredients are completely incorporated,
Immediately pour the dressing over the top of the salad. Serve immediately.