In a large pot or Dutch oven, heat 1 tablespoon of olive oil over medium heat. Add in the diced onion and cook for 2-3 minutes. Add in the garlic, fennel, and carrots. Cook until the onion is translucent, about 5-7 minutes. Deglaze the pan with some of the red wine (about 1/4 cup) and add in rosemary and thyme sprigs. Allow the vegetables to cook in the red wine until the liquid has reduced. Add in the rest of the wine, all of the stock, potatoes, and the fire roasted tomatoes. Season with salt, pepper, and red chili flakes.
Allow the soup to come to a boil, and then reduce to a gentle simmer. Let the soup simmer until the potatoes are fork tender, at least 30 minutes. The longer you allow the soup to cook, the better it will taste! (Note: you may need to add in a bit of water, as the potatoes will soak up a lot of the liquid.).
Shortly before you’re ready to eat the soup (10-15 minutes), remove the rosemary and thyme sprigs and add in the chopped kale. (I like the kale to retain some of it’s flavor and vibrancy, so I like to add it in at the end. It cooks very quickly.).
Once the kale is cooked (10 minutes, give or take), remove the soup from the heat. Serve while warm, and garnish with croutons and freshly grated parmesan cheese.