Heat a large pan or dutch oven over medium heat. Add the sliced chorizo and cook until lightly browned. Transfer to a plate and set aside.
Add olive oil to the pan and sauté the onion until softened and translucent. Add the garlic, smoked paprika, and oregano. Stir until fragrant, about 30 seconds.
Add the chopped tomatoes and cook until they begin to soften and break down. Stir in the tomato sauce, red wine, sugar, and bay leaves. Bring to a gentle simmer.
Add the diced potatoes, reduce heat to medium-low, and cover. Simmer for approximately 20 minutes, or until the potatoes are fork-tender.
Remove the bay leaves. Return the chorizo to the pan and add the calamari. Simmer gently for approximately 5–6 minutes, or until the calamari is just tender.
Taste and adjust the seasoning with salt and additional sugar if needed. Garnish with fresh parsley and serve hot.