Heat a heavy-bottomed dutch stockpot or Dutch oven over medium-high heat. Add the olive oil and heat for 30 seconds, till shimmering. Add the sausage (that has the casings removed) and brown, stirring occasionally with a flat bottomed wooden spoon, about 10 minutes. Transfer the browned sausage to a platter that's been lined with paper towels, set aside.
Add the diced bacon to the stock pot (Dutch oven) and brown until crispy, about 5 minutes. Remove from the pot and sit alongside the sausage on the platter to drain on the paper towels.
Add the potatoes, onions, fennel seed, and red pepper flakes. Cook for 10 minutes, stirring frequently until the onions become translucent the fennel becomes aromatic about 4 minutes, add the garlic stir in thoroughly and cook for an additional 1 minute.
Add the wine (if using) to deglaze the pot, stir and reduce to half, about 2 minutes.
Return the sausage and bacon to the pot. Pour in the stock and increase the heat to high, bring to a boil and then reduce the heat to medium. Allow the soup to cook on medium-high heat for an additional 25 minutes until the potatoes are tender and the flavors have blended.
Add the Kale and cook an additional 5 minutes till bright green and tender to the bite. Mix in the cream gently and stir thoroughly.