Preheat the oven to 350°F. Spread the torn bread onto a rimmed baking sheet and drizzle with 3 tablespoons of olive oil. Toss thoroughly, squeezing the pieces gently to help them absorb the oil. Season with kosher salt. Bake, tossing occasionally, for 15 to 18 minutes, until the croutons are deeply golden and crisp. Remove from the oven and let them cool.

In a medium bowl, combine the sausage and white wine. Using your hands, mix until the wine is fully incorporated into the meat. Heat a large Dutch oven over medium heat and cook the sausage mixture, stirring occasionally, for about 4 minutes. The meat should firm up without browning.

Add the diced onion, carrots, celery, chopped anchovies, sliced garlic, and red pepper flakes to the pot. Stir occasionally and cook until the vegetables become tender yet still hold their shape, about 20 to 25 minutes.

Toss in the torn kale, crushed tomatoes, and chicken broth. Bring the soup to a boil, then reduce the heat to a gentle simmer. Stir occasionally and let the soup cook for about 1 hour, allowing the kale to soften and the flavors to meld into a rich, hearty broth.

Just before serving, stir in the red wine vinegar and half of the toasted croutons, letting them break down slightly to thicken the soup. Ladle the soup into bowls, topping each portion with the remaining croutons. Garnish with generous shavings of Parmesan and a drizzle of high-quality olive oil. Enjoy!