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SALAD: Coarsely chop the lettuce, wash and throughly dry (I love a salad spinner for this step). Place lettuce in a large bowl. Top the salad with black olives, thinly sliced tomatoes, very thinly sliced red onion, and pepperoncini.
DRESSING: In a large mason jar add all the dressing ingredients: 1/3 cup red wine vinegar, 1 and 1/2 teaspoon Dijon mustard, 1/2 teaspoon dried oregano, 1/2 teaspoon Italian seasoning, 1 teaspoon white sugar, 1/2 cup olive oil, 2 tablespoons mayo, and salt & pepper to taste (I use 1/2 teaspoon salt and 1/4 teaspoon pepper). Put on the lid and shake to combine. It might take a minute of good vigorous shaking, but the mayo should completely integrate (keep shaking until it does). If you have time, make this ahead and chill in the fridge to intensify the flavors. Shake again right before mixing in to the salad.
ASSEMBLY: Right before eating (See Note 1), toss the salad with the dressing (you probably won't use all the dressing -- See Note 2). Add the croutons and freshly grated Parmesan cheese right on top and enjoy immediately.