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Heat the olive oil in a large Dutch oven over medium heat. Crumble in the chorizo. Sprinkle with salt and pepper. Cook, breaking up the chorizo with a wooden spoon, until browned, about 3 minutes. Add the red onion and bell peppers and cook until they begin to soften, 3 to 4 minutes. Add the garlic, jalapeno, ancho powder, cumin, smoked paprika and oregano. Cook and stir to coat the meat and vegetables in the spices, about 1 minute.
Add the tomatoes, beef broth and 2 cups water. Bring to a simmer over medium-low heat, then stir in the black beans and butternut squash. Simmer, uncovered, until the chili is thick and flavorful and the veggies are tender, 30 to 45 minutes.
Serve the chili with bowls of the toppings on the side for passing at the table.
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