Roast Squash and Sweet Potato Chili with Kale

Ingredients

~1½ pounds butternut (or other winter) squash, peeled and cubed (the peel and seeds add considerable weight, so you’ll need a 2½ to 3 pound butternut squash in order to yield 1½ pounds ready to cook; exact quantity isn’t critical, however)
~1½ pounds sweet potatoes (about 2; again, exact quantity isn’t critical)
~2 tablespoons olive oil for roasting the squash and sweet potatoes (extra virgin is better, but pure olive oil—the cheap stuff—works too)
Kosher salt to taste
freshly ground black pepper to taste
~2 cups diced onion (about 3 medium ones or 2 large; again, exact quantity not critical)
~1 tablespoon olive oil for sautéing onions
additional Kosher salt for seasoning onions (about ½ teaspoon)
3 to 5 garlic cloves (to taste)
2 to 3 large jalapeño peppers, diced fine (optional; to taste)
2 to 4 tablespoons mild or medium chile powder, or a mix of the two (see Notes for discussion and alternatives)
2 teaspoons chipotle chile powder (or to taste; may omit if you don’t like spicy)
2 tablespoons dried ground cumin
1 tablespoon dried ground coriander
2 tablespoons dried oregano
1 28-ounce can diced tomatoes
1 28-ounce can crushed tomatoes
water to thin the chili mixture
1 bunch kale (about ¾ pound)
3 to 4 15-ounce cans red kidney or pinto beans (or a mix of both; to taste)
garnish of reserved kale, jalapeño pepper slices, chopped parsley, chopped cilantro, and/or oyster crackers (optional)

Procedure

Start by roasting the squash and sweet potatoes (you can skip this step and instead cook these veggies in the chili, although you’ll lose a bit of flavor; see Notes): Preheat the oven to 400 degrees F. Peel the squash and cut it into ½- to ¾-inch dice (see headnote for instructions). Place the diced squash in a large bowl. Scrub the sweet potatoes, then dry and peel them. Cut the sweet potatoes into ½- to ¾-inch dice. Add the diced sweet potatoes to the bowl containing the squash. Add olive oil to the bowl and toss until the squash and sweet potatoes are evenly coated. Add Kosher salt and pepper to taste, then toss again. Spread the squash and sweet potato pieces out on a large rimmed baking sheet or a casserole baking dish. The pieces should be in one layer and should not touch (to promote even cooking). Roast the squash and sweet potatoes for 30 minutes (they’ll probably be just a touch underdone at this point, but they will finish cooking in the chili). Set the roasted squash and sweet potatoes aside until Step 10.
While the squash and sweet potatoes are roasting, proceed with the recipe: Peel the onion and cut it into dice of ½-inch or so.
Warm a Dutch oven—one that holds 6-quarts or more—over medium stovetop heat (you’ll be using this to cook the chili). When warm, add a tablespoon of olive oil and allow it to heat (it’ll shimmer when hot) and add the diced onion. Season with salt (about ½ teaspoon of Kosher, but your taste may vary), and cook until the onion is translucent and just beginning to brown (5 minutes or so).
While the onion is cooking, peel the garlic and mince it finely (or cut it into thin slices). Set aside.
Now wash the jalapeño peppers (if using) and cut them lengthwise. Use a teaspoon to scoop out the ribs and seeds (be careful, the oil on these is hot; keep fingers away from your eyes). Chop the peppers into very small dice (or use a mini food processor). Place the peppers in a bowl until you’re ready to use them, then wash your hands with soap and water to remove the hot jalapeño oil from your skin. You may want to reserve a slice or two of the pepper for garnish.
When the onion is just starting to brown, add the chopped garlic and jalapeño and cook for a minute or two.
Add all the spices—chile powder(s), cumin, coriander, oregano—to the onion mixture, then stir to combine. Add the canned tomatoes (both diced and crushed), plus one 28-ounce can of water to create a nice soup consistency.
Bring the chili to a simmer and allow it to cook for about an hour (or longer—timing not critical).
While the chili cooks, prepare the kale. Wash the kale and dry it well. Remove the center stems (just pull them out as you would when cleaning spinach). Chop the kale finely: The easiest way to do this is to take several leaves, roll them together lengthwise, then mince. You may want to turn your chopping board 90 degrees and mince again. (See Notes for more discussion; you may want to save a bit of kale for a garnish.) Refrigerate the chopped kale until ready to use (Step 12).
After the chili mixture has been cooking for an hour, add the roast squash and sweet potatoes. Pour the canned beans into a strainer and rinse them well, then add them to the chili.
Taste the chili and adjust seasoning if necessary (this would be a good point to add more chile powder if the mixture is not spicy enough for your taste; you’ll probably also need more salt). Add more water if too much has evaporated during cooking, or if you prefer a chili with a thinner consistency. Set a timer for 20 minutes.
At the 20-minute mark, add the kale to the chili mixture. Cook for another 10 minutes. The chili should now be done. You can hold it over low heat if you’re not ready to serve—or dish it up if you are. Garnish, if you wish, with some reserved kale (see Notes). Or try jalapeño pepper slices, chopped parsley, or chopped cilantro. Oyster crackers are also a nice addition. (See Notes for more garnish options.)

From kitchenriffs.com