Make the Lemon Caesar Dressing:
- In a blender or small food processor, combine the lemon juice, garlic cloves, Dijon mustard, capers, anchovy filet, Worcestershire sauce, kosher salt, and black pepper. Turn the blender on medium and combine.
- Slowly stream in the olive oil while the blender is on, until the oil is fully combined and is thick and emulsified. Pour the dressing into a small bowl and add 2 ounces of the finely grated Aged Cheddar Cheese.
- Preheat the oven to 425 degrees F. Place the sliced squash on a parchment lined baking sheet, and drizzle generously with 2 tablespoons of olive oil. Then, sprinkle on the chili powder, kosher salt, and ground black pepper. Toss the squash so that every piece is coated in the oil and spices. Roast for 20-25 minutes until the squash is deeply caramelized.
- On a separate baking sheet, spread the torn croutons into an even single layer. Drizzle the melted butter on top, and sprinkle with the ground garlic powder, and a generous pinch of kosher salt. Bake for 6-8 minutes until the croutons are golden brown and toasted. Keep an eye on them so that they don’t burn.
- Assemble the salad: In a large bowl, add the leafy little gems or artisan lettuce leaves. Drizzle generously with the lemon Caesar dressing, and toss to coat the leaves thoroughly. Add the pieces of roasted squash and drizzle a bit more dressing on top.
- Finally, add the toasted buttery croutons to the bowl, and top the whole salad with more finely grated Aged Cheddar cheese. Add freshly cracked black pepper, and serve immediately.