Preheat the oven: Set a rack in the middle of the oven and preheat to 400 °F / 204 °C.
Prep the kale: Wash ½ bunch lacinato kale in cold water, preferably in a salad spinner if available. Arrange leaves on a large, clean kitchen towel and allow them to dry.
Massage the kale: To a large salad bowl, add kale, 2 teaspoons of olive oil, and a pinch of salt and pepper to taste. Err on the side of less salt.Massage the kale by running your fingers through the leaves as you squeeze and rub them together. The whole process should take about 1 - 2 minutes, and as you continue massaging the leaves, they will soften considerably. Once the leaves feel soft and tender, set aside.
Bake the croutons: On a parchment-lined baking sheet, coat 1 cup crusty bread with 1 tablespoon olive oil, and season with salt and pepper to taste.Bake for 6 - 8 minutes, flipping the croutons in between until they are golden-brown and crunchy around the edges but still slightly soft in the center (they will continue to cook slightly after removing from the oven, so err on the slightly softer side). Remove from the baking sheet and transfer to a bowl to cool to room temperature.
Prepare the Dressing:
Make the anchovy paste: Mince 1 anchovy filet (or capers), then place the grated 1 small garlic clove and a pinch of salt on top of the minced anchovy. Mash the anchovy, garlic, and salt together until it forms a paste; to help create a paste, tilt your knife at a 30 degree angle and scrape the knife across the anchovy mixture. Next, mince the mixture with your knife for a few seconds, then repeat, scraping then mincing until it forms a paste.
Finish the dressing: Transfer paste to a small bowl, and whisk in ½ teaspoon dijon mustard, 2 tablespoons grated parmigiano-reggiano cheese, and ⅓ cup full-fat mayonnaise. The dressing should now be a thick paste. Slowly drizzle in 1 tablespoon extra-virgin olive oil and 1 ½ teaspoons freshly squeezed lemon juice, then season to taste with salt and pepper.
Taste the dressing: To test if the dressing suits your preferences, dip a piece of the kale into the mixture and taste it. The bite should taste garlicky, with a slight bit of acidity and saltiness.You want it to taste slightly less “zingy” than you want it, because when you eat the salad, you'll be eating many bites, so the punchy flavors and zinginess will build up over time. Note: Too strong or thick? Dilute the mixture with some olive oil (or water if you don't want to add more oil). Too subtle? For additional zinginess, add more garlic or mustard; for additional saltiness, add more salt or anchovy; for additional acidity, add more lemon juice.
Serve:
Once you're satisfied, toss the kale with about half the dressing to start. If desired, add the remaining half of the dressing, along with the croutons, and shaved parmigiano cheese. Serve immediately.
Video
Notes
The Caesar dressing is thicker than you might be used to -- but if the kale is massaged well and has a nice coat of olive oil, it should be just the right consistency when you dip a piece of kale in the dressing to try it out.Storage:
Dressing: Dressing can be made-ahead and stored in an airtight container in the fridge for 3 - 4 days.
Make-Ahead: I don't recommend fully prepping the kale in advance, but you can definitely wash, dry, wrap it in a paper towel, then store in a Ziploc bag in the fridge for a day or two.
Homemade croutons can be prepared in advance, stored in the freezer for up to 4 weeks and reheated at 325°F (163°C) until warm and toasty.