Prep your ingredients. Dice the onion and bell pepper, mince the garlic, and cube the butternut squash into bite-sized pieces. Rinse and drain the beans.
Brown the meat. In a large pot or Dutch oven, heat 1–2 tablespoons of olive oil over medium-high.
Add the ground beef or turkey. Cook until browned, breaking it up as it cooks. Season with a pinch of salt and pepper, then transfer to a plate, leaving a bit of fat in the pot.
Sauté the aromatics. Add the onion and bell pepper to the pot.
Cook for 4–5 minutes, stirring, until softened. Add the garlic and cook for 30 seconds, just until fragrant.
Bloom the spices. Stir in chili powder, cumin, smoked paprika, and cinnamon. Cook for 30–60 seconds to wake up the spices.
If the pot looks dry, add a drizzle of oil.
Build the base. Stir in tomato paste and cook for another minute. Add crushed tomatoes, broth, and apple cider. Scrape the bottom of the pot to release any browned bits.
Add the hearty stuff. Return the browned meat to the pot.
Add the butternut squash, beans, bay leaf, and optional chipotle or cayenne if using. Bring to a gentle simmer.
Simmer slowly. Reduce heat to low and cook for 30–40 minutes, stirring occasionally, until the squash is tender and the chili has thickened. Add more broth if you prefer a looser consistency.
Taste and adjust. Remove the bay leaf.
Taste and adjust salt, pepper, and heat. If you want a touch more brightness, stir in a teaspoon of apple cider vinegar or a squeeze of lime.
Serve with toppings. Ladle into bowls and finish with your favorite toppings. A dollop of Greek yogurt, sharp cheddar, and cilantro make a great combo.