01 -
Preheat broiler and position rack a few inches below. Halve peppers lengthwise, remove seeds, and place cut side up on a foil-lined baking sheet. Broil until skin chars evenly, about 1 minute. Wrap peppers in foil allowing air inside, let steam 5 minutes. Remove skins and finely chop. Measure ¼ cup and set aside.
02 -
Preheat oven to 475°F. Line a baking sheet with parchment paper. Trim squash ends, peel using a chef's knife, and remove seeds with a spoon. Dice squash into ¼ to ½-inch pieces and transfer to a bowl. Toss with 3 tablespoons olive oil, brown sugar, cinnamon, and ¾ teaspoon salt. Spread evenly on the baking sheet and roast for 20 minutes, stirring halfway until golden.
03 -
Heat remaining olive oil in a Dutch oven or large pot over medium heat. Add chopped onion and minced garlic. Cook until onion begins to brown, approximately 7 minutes.
04 -
Incorporate the chopped jalapeños, chipotles in adobo, ground cumin, and chili powder into the pot. Cook stirring for about 1 minute until aromatic.
05 -
Reduce heat to low, pour in red wine. Increase heat to medium-high and simmer until wine is reduced by half, roughly 4 minutes.
06 -
Add diced tomatoes with their juices, drained kidney and Cannellini beans, and roasted butternut squash to the pot. Stir to combine, lower heat, cover, and let simmer for 15 minutes to meld flavors.
07 -
Stir in fresh oregano and season with salt and pepper to taste (approximately 1 teaspoon kosher salt). Adjust seasoning as needed.
08 -
Offer avocado, shredded cheddar, sliced red onion, and sour cream as garnishes if desired.