Heat a large Dutch oven over medium heat. Add the bacon and cook for 8-10 minutes until crisp and golden. Remove the bacon with a slotted spoon to a bowl.
Add enough extra virgin olive oil to the bacon fat in the pot to equal 2 tablespoons. Add the diced onion, bell pepper, celery and jalapeno and stir to combine. Cook for 4-5 minutes until softened. Add the garlic, oregano, cumin, coriander and chili powder and stir for another minute to bloom the spices. 1 large sweet onion, 1 large red bell pepper, 2 medium celery stalks, 1 medium jalapeno, 6 medium garlic cloves , 1 ½ tablespoons dry oregano, 1 tablespoon cumin, 1 tablespoon coriander, 1-2 teaspoons mild-medium chili powder
Push the veggies to the sides of the pot and add the Italian sausage. Cook until nicely browned, breaking it up with a metal spatual or spoon and stirring occasionally. 8 ounces mild or sweet Italian sausage
Stir the mixture to combine the veggies and Italian sausage then add the ground turkey, again, breaking it up into bite size pieces with a metal spatula or cooking spoon. Cook for 4-5 minutes or until the ground turkey looses all of it’s pink color. Don’t worry it won’t brown, you just want it cooked through. 1 ½ pounds ground turkey
Add the tomato paste and continue to cook for 2-3 minutes, stirring frequently. ¼ cup tomato paste
Add the crushed tomatoes, chicken broth, drained black beans, pumpkin puree, reserved bacon, 1½ teaspoons of kosher salt and black pepper. Stir to combine, then bring the mixture to a boil. Reduce to a steady simmer and cook for 45 minutes, adding a bit more chicken broth if the chili seems to be getting too thick. Taste and add more salt, if needed. 28 ounces fire-roasted crushed tomatoes, 3 cups low sodium chicken broth, 15 ounces can of pumpkin puree, 3 15-ounce cans black beans, 1 ½ teaspoons kosher salt, 1 teaspoon ground black pepper