Caesar Dressing: In the bowl of a food processor, combine the Lemon Juice (1/3 cup), Dijon Mustard (1 tablespoon), Garlic (1 clove), Anchovy (1), Egg (1), Kosher Salt (1/2 teaspoon) and Ground Black Pepper (1/2 teaspoon). Pulse until combined.
With the processor running, add the Extra-Virgin Olive Oil (1/2 cup) in a slow stream. Add the Pecorino Romano Cheese (1/3 cup) and pulse until just combined. Refrigerate in a sealed container until ready to use.
Preheat the oven to 400 degrees F (200 degrees C) and arrange two evenly spaced oven racks.
Spread the Cornbread (3 cup) and the kernels cut from Corn (4 ear) onto two separate sheet pans. Drizzle the corn with the Extra-Virgin Olive Oil (1 tablespoon) and toss to combine.
Sprinkle each sheet pan lightly with Kosher Salt and Freshly Ground Black Pepper (to taste). Roast for 15 minutes, tossing the cornbread and corn halfway through. Set aside to cool.
Meanwhile, chiffonade the Tuscan Kale (3 bunch): cut along each side of the rib to remove the leaves on each side. You should end up with two long strips from each rib.
Roll the leaves lengthwise into “cigars” and slice them thinly crosswise to cut the kale into ribbons. Wash the kale and dry it using a salad spinner.
To assemble the salad, pour the dressing over the kale and toss well. Add the corn, croutons, and the Pecorino Romano Cheese (1/2 cup) and toss again. Serve immediately or refrigerate for up to several hours, bringing the salad back to room temperature before serving.