1 lb. dried black beans, soaked overnight
1 t. cumin seed
2 T. dried red bell pepper
3 bay leaves
1 medium or large butternut squash
1/2 onion, finely chopped
2 small or 1 large green bell peppers, diced into 3/4 inch cubes
15 oz. crushed tomatoes
1 c. frozen corn or more to taste
2 t. powdered cumin
2 t. oregano
salt and pepper to taste
splash of balsamic vinegar and/or honey to adjust flavors as needed
fresh cilantro, washed and cleaned
powdered chipotle pepper
cheddar cheese if desired
Drain the black beans in the morning and put into a 5-quart crockpot on high. Cover with water; add cumin seed, dried bell pepper, and bay leaves. Check after a couple of hours to see if more water is needed. If you're going to leave them all day, reduce heat to low.
About 2 hours before dinner, or a day ahead of time if you want to have the squash prepped, wash the squash and poke a couple of holes in it. Roast at 400F on a baking sheet for about an hour. Remove from oven, slice off the top and bottom, split down the middle lengthwise, and allow to cool enough to handle.
Take the seeds out of the squash and set aside. Peel the squash and cut into cubes. Place squash cubes back on the baking sheet, add a little olive oil, and toss. Return to oven for about 15 minutes. Put the bell pepper pieces on another baking sheet and roast for about 5-10 minutes - you'll know when they're done. Don't let them get too blistered.
Add the squash and the bell pepper to the chili. Add remaining ingredients at this time, except for the vinegar/honey.
While the chili is cooking, clean the squash seeds. Put on a baking sheet and bake in the oven to drive off the moisture. If the oven is still at 400, this will only take about 5 minutes and the seeds will burn quickly. Adjust oven temp as needed for any other cooking that's happening, such as cornbread to go with the chili. Remove seeds from the oven, stir around, add a little olive oil, chipotle pepper powder, and salt. Return to oven until lightly toasted, then remove and let cool.
Taste the chili and adjust seasonings as needed. Serve the chili with fresh cilantro, the chipotle squash seeds, and, if desired, grated cheddar cheese.