1. Preheat the oven to 375F degrees.
2. Place the butternut squash on a large rimmed baking sheet and drizzle with 2 tablespoons of olive oil and a pinch of salt and pepper. Toss squash to coat evenly and roast in preheated oven for 25-30 minutes, turning pan and rotating squash once or twice so it evenly browns.
3. Remove from oven. Meanwhile, heat chicken or vegetable stock in a small sauce pan and bring to a simmer. Turn to low and keep stock warm.Over medium heat, add remaining 1 tablespoon of olive oil and butter to a large heavy bottomed stock pot.
4. Add onion and saute 10-12 minutes until soft and golden.
5. Add minced garlic and barley. Stir for 1 minute until garlic is fragrant and barley is glossy and coated in butter and oil. Turn the heat to medium-high and add white wine. Stir and let the wine evaporate. Use a lade and begin adding the stock about cup at a time, stirring after each addition. When the stock is just about evaporated, add more. The barley shouldnt be soupy or dry. Play with the heat and keep it between medium and medium-high and stir frequently. Begin tasting the barley about 25 minutes after you initially add it. In the end you want the barley to be tender but still have a tiny bit of crunch; this could take as long as 35-40 minutes. You might use all the stock but might notkeep extra on hand just to be safe! Stir in the kale and parmesan and let season the risotto with salt and pepper. If risotto gets too thick, stir in additional 1/4 cup stock if needed (a few tablespoons at a time) until you have desired consistency.
6. Serve warm topped with butternut squash.