Step 1: Preheat your oven to 400°F (200°C). Toss the cubed butternut squash with 1 tablespoon of olive oil, salt, and pepper on a baking sheet. Roast for 25-30 minutes, or until tender and lightly caramelized. Remove from oven. Reserve about 1/2 cup of roasted cubes for garnish, then mash the remaining squash with a fork or potato masher. Set aside.
Step 2: While the squash roasts, prepare the crispy sage. In a small skillet, heat 1 tablespoon of olive oil over medium heat. Add the fresh sage leaves and fry for 1-2 minutes, until crisp and fragrant. Remove with a slotted spoon and place on a paper towel-lined plate to drain. Sprinkle with a tiny pinch of salt. Set aside.
Step 3: In a medium saucepan, gently warm the vegetable or chicken broth over low heat. Keep it at a simmer throughout the cooking process; do not let it boil.
Step 4: In a large, heavy-bottomed pot or Dutch oven, heat the remaining 1 tablespoon of olive oil over medium heat. Add the chopped onion (or shallots) and cook until softened and translucent, about 5-7 minutes. Stir in the minced garlic and cook for another minute until fragrant.
Step 5: Add the Arborio rice to the pot. Stir constantly for 2-3 minutes, toasting the grains until the edges become translucent but the center is still opaque.
Step 6: If using, pour in the white wine and stir until it is completely absorbed by the rice. Let the alcohol evaporate, which should take about 2 minutes.
Step 7: Begin adding the warm broth, one ladleful (about 1/2 cup) at a time, stirring constantly. Wait until each ladleful is almost fully absorbed by the rice before adding the next. Continue this process for 20-25 minutes, or until the rice is creamy and al dente (tender with a slight bite in the center).
Step 8: Stir in the mashed butternut squash until it is fully incorporated and the risotto has a beautiful orange hue.
Step 9: Remove the pot from the heat. Stir in the unsalted butter and grated Parmesan cheese. Continue stirring vigorously until the butter and cheese have melted and the risotto is wonderfully creamy and glossy. Taste and adjust seasonings as needed.
Step 10: Serve the Creamy Roasted Butternut Squash Risotto immediately, garnished with the reserved roasted squash cubes, a sprinkle of extra Parmesan, and plenty of crispy sage leaves.