Preheat oven to 425°F. Tear bread into bite-size pieces (about 5 cups).
Toss with 3 tablespoons olive oil, salt, and pepper.
Bake on a rimmed baking sheet, tossing halfway, until golden and crisp, 14-16 minutes. Let cool.
Dice Fontina or provolone cheese.
Chop Kalamata olives and Peppadew peppers.
Thinly slice iceberg lettuce and red onion. Halve or quarter cherry tomatoes.
Drain pearl mozzarella. Cut deli ham and salami into strips.
Combine cheese, olives, Peppadews, lettuce, onion, tomatoes, mozzarella, ham, salami, and croutons in a large bowl.
Drizzle with red wine vinegar and 2 tablespoons olive oil.
Add oregano, salt, and pepper. Toss to coat.
Adjust seasoning if needed.
Divide salad among plates. Add extra black pepper. Serve immediately.