Prep the kale. Use a sharp knife or your hands to strip the kale leaves from the stems. The stems are woody and don’t break down very well. Roughly chop the kale into bite sized pieces and transfer to a bowl. Sprinkle the kale with a small amount of kosher salt and use your hands to massage the pieces until they’re tender. Set aside.
Crisp up the bacon. Heat the olive oil in a 4-5 qt dutch oven over medium heat. Once the oil is hot, add the bacon and cook for 6-8 minutes, stirring often, until the bacon is crispy. Use a slotted spoon to transfer the bacon to a small bowl and discard all but 1 tablespoon of bacon fat (or save for another application!).
Cook the sausage and veggies. Lower the heat slightly and add the italian sausage. Use a wooden spoon to break the sausage up as it cooks and cook until browned. Once the sausage is cooked, add the onions, carrots, and fennel to the pot and saute for 5-6 minutes, until the vegetables are soft. Stir in the dried oregano, basil, red pepper flakes, and garlic and cook for another minute.
Simmer the soup. Pour in the chicken stock and bring to a gentle simmer for 10 minutes. Stir in the ravioli and bacon and cover. Simmer for 3-4 minutes, then pour in the heavy cream and add the chopped kale and basil leaves. Simmer for another 2-3 minutes, until the kale is tender. Stir well and season to taste with salt and pepper.
Ladle the soup into bowls and top with parmesan, basil, and a drizzle of olive oil.