Roast Squash & Sweet Potato Chili with Kale

This vegan crowd pleaser is perfect for Thanksgiving Eve

All of us in the US know Thanksgiving is coming up, right? And you probably know what you’ll be serving for the big meal. But how about the evening before?

Some picky out-of-town guests may be arriving on Thanksgiving Eve. You know the ones we mean: That college student who turned vegetarian. The fussy in-law who insists on having the latest food-fad ingredients at every meal. And so on.

Fortunately, this Roast Squash and Sweet Potato Chili with Kale covers all the dietary bases. It’s vegan, so it will appeal to non-carnivores. But it’s also chili (aka flavorful guy food), so meat eaters won’t mutiny. And it has kale, so it should pass muster with the food faddists. It’s even gluten-free.

Best of all? It’s easy to make. In fact, it’s basically a one-dish meal. So you’ll save time cooking—which will give you more time for arguing around the dinner table. Ah, those family gatherings.

Recipe: Roast Squash & Sweet Potato Chili with Kale

The sweet flavor of winter squash works perfectly in a spicy dish like chili. Any winter squash will work, though we prefer butternut squash in this dish. We like to add sweet potatoes for another flavor note, but you could use squash alone if you prefer.

When preparing butternut squash, the biggest challenge is peeling and cubing it. For a terrific photo tutorial on how to do this, click on over to Alanna Kellogg’s A Veggie Venture. Alanna has forgotten more about winter squash than we’ll ever know.

Now that you’ve seen the photos, here’s a quickie recap on prepping butternut squash: First, make sure you have a sharp knife. Second, cut just a bit off the bottom of the squash (to create a stable base) and a bit off the top (because you don’t want to eat that). Third, cut off the “neck” (the skinny part) of the squash right above the more bulbous body. Fourth, with your sharp knife, slice the skin off the lower body of the squash—much like you’d cut the peel off an orange. Then slice the skin off the neck of the squash. Fifth, cut the neck into chunks of ½- to ¾-inch. Then cut the body of the squash in half vertically, scoop out the seeds, and cut the squash into chunks of ½- to ¾-inch.

Prep time for this dish is about 20 to 30 minutes. Cooking time adds about an hour and a half (much of it unattended).

This recipe yields a lot—4 quarts or so, perfect for feeding a crowd. It will freeze OK, although the squash may become a bit soft (it still tastes good; but the texture won’t be quite as firm).

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

1. 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.
2. 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.
3. 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).
4. While the onion is cooking, peel the garlic and mince it finely (or cut it into thin slices). Set aside.
5. 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.
6. When the onion is just starting to brown, add the chopped garlic and jalapeño and cook for a minute or two.
7. 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.
8. Bring the chili to a simmer and allow it to cook for about an hour (or longer—timing not critical).
9. 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).
10. 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.
11. 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.
12. 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.)

Notes

• If you don’t want to roast the squash and sweet potatoes, you can cook them in the chili. Clean, peel, and cut the squash and sweet potatoes as directed in Step 1, then add them when the chili has been cooking for half an hour or so.
• A refresher on the difference between “chile” and “chili” powder: When you dry chile peppers and grind them up, you produce chile powder. Chile powder contains nothing but chilies. By contrast, chili (with an i) powder is a mixture of herbs and spices that includes chile powder as one of its ingredients. Peppers and powders can both be used to flavor the dish called “chili.”
• You don’t need to use a specific chile powder for this recipe. We use both mild and medium dried Hatch chile powders, as well as chipotle powder. (No need to mix the Hatch powders though; you can use one or the other if you don’t want to buy both.) Ancho chile powder (which is sold in many supermarkets) also has great taste and is fairly mild. If you can’t find chipotle powder, you can substitute cayenne (but use only half as much), or just leave it out. Chipotle powder has a nice smoky flavor that adds an interesting dimension to this dish, but it’s not essential. In any case, don’t stress over the varieties—just buy whatever chile powders your supermarket stocks.
• This recipe specifies 2 to 4 tablespoons of mild and/or medium chile powder. Using 2 tablespoons produces a batch of chili that we regard as mild in flavor, with just a slight ping of heat to it. But that’s our palates—your taste will differ (in fact, we always use 4 tablespoons because we like spicy). You may know from experience that the quantity of chile powder we call for is too much or too little for you. If you’re concerned about the heat level, start with 1 or 2 tablespoons, then taste the chili after it has been simmering for about 30 minutes. This is a good point to adjust the chile powder level. Don’t wait until the end to adjust, because chile powders need time to simmer in order to develop the full depth of their flavor.
• You can substitute chili powder for the chile powder(s) in this recipe. If you go that route, use 3 to 5 tablespoons of chili powder. Reduce the cumin, coriander, and oregano by about half, or eliminate them altogether (since these flavors are already incorporated into chili powder). The taste of the finished dish won’t be as crisp if you use chili powder, but you’ll still be pleased with it.
• You should chop the kale finely because you’ll be cooking it for a relatively brief time (big pieces of kale are not pleasant to eat when they’re raw or lightly cooked). If you don’t want to bother with chopping the pieces so finely, just cook the kale longer—a half hour or so (add it with the beans in Step 10). Note, however, that when kale cooks longer, it loses its bright green color; the hue becomes much more muted.
• Canned beans are easy to use in this recipe and have acceptable flavor, but make sure you wash off the gunk they’re packed in (Step 10). Dark red kidney beans work best in chili, though we also like pinto beans in this dish (and often mix the two).
• If you prefer to substitute dried beans for canned (we often do), prepare a pound of dried beans.
• How to prepare dried beans? The easiest way is the “quick-soak” method: Sort through the beans, looking for dirt or stones; then rinse off the beans and pour them into a 4-quart (or larger) pot. Fill the pot with water to within a couple inches of the rim; place the pot on the stove and bring it to a boil. Boil for two minutes, then turn off the stove and cover the pot; let it sit for an hour. Once the hour is up, drain the beans; then place them in a smaller cooking pot and cover them with about an inch of water. Add a peeled and halved onion and several cloves of garlic (peeled or not) for flavoring, then bring the beans to a simmer. Simmer until they’re tender—typically about an hour to an hour and a half for kidney beans. Drain the beans, then add them to the cooking chili in Step 10.
• Kosher salt is more coarse than regular table salt, so it’s less salty by volume. If you’re substituting table salt for Kosher, always use less—about half as much. If the dish isn’t salty enough, you can always add more later.
• If you like thick chili, cook it a bit longer to evaporate more of the liquid. If you prefer a thinner, soupier mix, you can add some water at the end to achieve the consistency you prefer.
• Are you planning to reserve some kale for garnish? It will have better color if you blanch it in boiling water for 20 seconds or so. After blanching, drain the kale and rinse it under cold water to stop the cooking. This is a very optional step, though—it will work fine if you add the raw kale right before serving.
• In addition to the garnishes suggested in the ingredients list and in Step 12, you might also consider grated cheddar cheese, a sprinkle of diced raw onion, or a dollop of sour cream or Greek yogurt.

Chili con Corny

“Kale surprise,” said Mrs Kitchen Riffs, using her best French accent.

“Yup, it’s chili in here,” I said, dipping a spoon into my bowl.

“But I thought you were roasting,” said Mrs K R.

“I was,” I said. “So I guess we have some real hot potatoes to deal with.”

“Potatoes?” said Mrs K R. “Sweet.”

We need to squash these puns.

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