Add the diced bacon to a large enameled cast iron dutch oven. Cook over medium-high heat until nice and crispy, about 5 minutes. Remove the bacon from the pan with a slotted spoon and let cool on a paper-towel lined plate.
Next, add the uncooked Italian sausage to the dutch oven. Use a spatula to break up the meat, and let it cook until well browned and broken up into small pieces, about 10 minutes. Use a slotted spoon to remove the sausage to a bowl, and set aside for later.
Add the diced onion to the dutch oven, and let cook in the bacon/sausage fat until softened and just lightly golden, about 8 minutes.
Add the garlic, salt, pepper, and oregano to the dutch oven and let cook for a minute or so until fragrant.
Add the potatoes to the dutch oven and toss to combine with the onions and spices. Pour the chicken broth into the pot, increase the heat to high, and bring to a boil. Reduce the heat to a simmer & let cook for about 15 minutes, until the potatoes are tender.
Once the potatoes are tender, stir the kale into the soup along with the reserved sausage. Let cook for just a few minutes, until the kale is tender.
Add the half and half to the pot and bring to a simmer.
Turn off the heat and ladle the soup into serving bowls. Sprinkle with the crispy bacon bits and season each bowl with a sprinkle of salt & freshly ground black pepper. Enjoy!