Preheat the oven to 400°F.
Cut the top off the head of garlic to expose the cloves. Drizzle with 1 tablespoon of olive oil and sprinkle with salt and pepper. Wrap in aluminum foil and roast for 30-35 minutes, until soft and golden.
While the garlic is roasting, prepare the kale. In a large bowl, massage the chopped kale with 1 tablespoon of olive oil and lemon juice until the leaves are tender, about 2-3 minutes.
Once the garlic is done, let it cool slightly, then squeeze the roasted cloves out of their skins into a small bowl. Mash the garlic with a fork and mix it into the Caesar dressing.
Add the garlic-infused dressing to the kale and toss until evenly coated.
Top with croutons and grated Parmesan cheese. Serve immediately.