In a large Dutch oven, heat two tablespoons of olive oil over medium-high heat. Add the Italian sausage and brown, breaking it into crumbles. Keep the sausage in the pot, but move it to one side of the pot.
Add chopped onion and minced garlic to the open side of the pot. Sauté until softened and fragrant, about 3–4 minutes. Season with freshly cracked black peppercorns and a pinch of kosher salt. Stir to combine.
Push the onions aside slightly and add two tablespoons of tomato paste. Cook for 2–3 minutes to deepen the flavor.
Add 5 cups of chicken or vegetable stock and stir until well combined.
In a blender, add the entire 28-ounce can of whole peeled tomatoes. Blend until smooth, then add to the pot along with the 14-ounce can of crushed tomatoes.
Stir in 1 tablespoon granulated garlic, one tablespoon granulated onion, one tablespoon smoked paprika, 1–2 tablespoons Italian seasoning, and two tablespoons fresh lemon juice.
Add 2 cups of chopped kale. Reduce the heat to medium-low, cover, and let the soup simmer for about 15 minutes.
Open the lid and stir in 1 cup of heavy cream to add richness.
Add the 10-ounce package of cheese tortellini. Stir, cover, and cook until the tortellini are al dente, about 5–7 minutes.
Stir in fresh basil, if using. Taste and adjust the seasoning with additional Kosher salt and freshly cracked black pepper as needed.
Serve hot, topped with grated Parmesan cheese.