01 -
Preheat broiler and position rack several inches below. Halve the jalapeños lengthwise, remove seeds, and place skin-side up on a foil-lined baking sheet. Broil until skin chars evenly, about 1 minute. Remove and enclose peppers loosely in foil for 5 minutes to steam. Peel off skins, finely chop, and measure ¼ cup. Set aside.
02 -
Preheat oven to 475°F and center the rack. Line a baking sheet with parchment paper. Trim ends of squash, peel, remove seeds, and cut into ½-inch cubes. Toss squash with 3 tablespoons olive oil, brown sugar, cinnamon, and ¾ teaspoon salt until evenly coated. Spread in a single layer on the baking sheet and roast for 20 minutes, stirring halfway, until golden brown.
03 -
In a large Dutch oven, heat remaining olive oil over medium heat. Add chopped onion and minced garlic, cooking until onions begin to brown, about 7 minutes.
04 -
Incorporate the chopped roasted jalapeños, chipotles in adobo, ground cumin, and mild chili powder into the pot. Stir and cook until fragrant, approximately 1 minute.
05 -
Reduce heat to low, pour in red wine, then increase heat to medium-high and simmer until wine reduces by half, about 4 minutes.
06 -
Add diced tomatoes with juices, red kidney beans, cannellini beans, and roasted butternut squash. Lower heat to simmer, cover, and cook for 15 minutes to meld flavors.
07 -
Stir in fresh oregano and adjust seasoning with salt and pepper to taste. Recommended: 1 teaspoon kosher salt or half that amount if using table salt. Serve with optional toppings as desired.