To roast butternut squash, preheat oven to 500 degrees, and line a large baking sheet with parchment.
Toss butternut in 3 Tbsp of olive oil and season generously with salt. Place on the bottom rack of the oven for 5-7 minutes, then toss the cubes and return to the center rack. Reduce heat to 450 and bake for 10-12 more minutes. Remove when squash is browned and just fork tender—it's okay if they aren’t fully cooked, as they will continue to cook in the chili. Set aside.
NOTE* This step is to build flavor, by browning the squash. If you don’t want to roast the butternut, simply cut into 1/2’’ cubes and add it to the chili along with the onions, pepper, and garlic.
To roast the hatch chilis, preheat broiler to 500. Place chilis on a baking sheet and broil 4-6 minutes per side, or until charred and peeling. Place in a bowl and cover with plastic wrap to steam. Once steamed and cooled, peel off the skin and remove the seeds. Cut into 3/4’’ pieces and set aside.
In a small mixing bowl, combine the oregano, cayenne pepper, cumin, coriander, pepper, and salt. Set aside.
In a large pot or Dutch oven, add 3 Tbsp olive oil and hat over medium-high. When shimmery and hot, add the onion, green bell pepper, garlic, and a generous pinch of salt. Lower heat to medium-low and cook until softened—10 minutes. If you are NOT roasting the butternut, add it to the pot now.
As the vegetables cook down, heat 2 Tbsp oil in a pan over medium-high heat. Add half of the meat in a single layer and sprinkle with half of the seasoning. Let sit, untouched for 3-4 minutes, to brown the bottom, then break into smaller pieces and cook for 3-4 minutes more. Transfer to the pot. Repeat with the remaining spice and meat—add more oil to the pan if needed.
Once the meat is in the pot, add the chicken stock, white wine, Worcestershire, hatch chilis, and beans. Stir to combine, bring to a boil, then reduce heat and simmer for 45-60 minutes, stirring occasionally.
Serve warm with sour cream, purple cabbage, fresh cherry tomatoes cilantro, avocado, sharp white cheddar, and fresh-squeezed lime.