In 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 and sprinkle the grated parmesan over everything.
In a small mixing bowl or a quart-sized mason jar, combine olive oil, white wine vinegar, water, mayonnaise, sugar, minced garlic, lemon juice, Italian seasoning, kosher salt, black pepper, and red pepper flakes.
Whisk or shake until well combined to create a smooth dressing.
Immediately pour the dressing over the top of the salad and toss gently. Serve right away.