The perfect one-pot meal for cooler weather, this chili is as delicious as it is pretty. It's full of warming spices and hearty vegetables, and is a true bowl of comfort.
Roast the jalapeño peppers: Preheat the broiler. Cut each one in half and remove all of the seeds. Place the peppers round side up on a foil-lined baking sheet and put it directly under the broiler until the skin is fairly evenly charred, just for a minute or so. Remove from the broiler and then wrap them in the foil you broiled them on, leaving at least a few inches of air inside. Let them steam this way for about 5 minutes. Use your hands or the dull side of a paring knife to remove the skin. Finely chop the peeled peppers and set aside two tablespoons of them to add to the chili.
Preheat the oven to 475°F and line a baking sheet with foil.
Roast the squash: Add the cut butternut squash to the foil and drizzle it generously with olive oil. Then sprinkle with the brown sugar and cinnamon and toss to evenly coat all of the squash. Place in the preheated oven until the squash becomes golden brown, about 10 minutes per side.
Cook the onion and garlic: While the squash is roasting, coat the bottom of a large stock pot or Dutch oven with olive oil. Add the onion and garlic and over medium heat, cook until the onion begins to brown, about 4 minutes.
Add in the 2 tablespoons of the finely chopped jalapeños, along with the chipotles, cumin, and chili powder. Cook until it becomes very aromatic, about 1 minute.
Deglaze the pan: Then turn the heat to low and deglaze the pan with the wine.
Season: Add the oregano and season to taste with salt and brown sugar.