(Note: this post was originally published on February 20, 2019. It was one of the earliest recipes on The Rogue Brussel Sprout! (Hence the awful photos... sorry!... I promise it's on my list to rephotograph this soon). The date above reflects migration to the new platform.)

Chili: A Love Language

Chili is to food what a blank canvas is to art. It has the potential to become a masterpiece, and is just waiting to be filled with delicious inspiration. It truly is one of my favorite things to make.

Chili is also a labor of love, or at least it is in my opinion. This is not a "set it and forget it" slow cooker recipe (sorry!!). To be honest, I don't generally find slow cooker stews to be all that exciting because all of the ingredients have been cooked the same way. Life gets much more interesting when you caramelize, roast, toast, and char; after all, that's where the flavor comes from.

This chili is a project for a cold winter afternoon when you want to have fun in the kitchen, sip a margarita two, and watch the magic happen. Creating all these levels of flavor is a hands-on process, so make a big batch and savor your leftovers for days!

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A Balancing Act

In my mind, one of the most important aspects of chili is balance. Chili that is one-note (for example, super spicy) or one texture (uniform slow-cooker mush) can feel boring. When I make chili, my goal is to achieve a diverse array of flavors and textures.

In this version, I bring in some non-traditional flavors with one of fall/winter's most iconic ingredients: squash! The combination of the delicate sweetness of the squash with the spiciness of the peppers and chili powder is magical. I've found that the key to bridging the gap is to use pumpkin puree instead of tomato paste as the base, sort of an orange chili rather than a red chili if you will.

In this recipe, I try to hit on all the flavor notes. There's sweet (squash and pumpkin), spicy (peppers and spices), roasty (grilled corn, caramelized onions, fire-roasted peppers), nutty (wheatberries), warming (cinnamon and ginger), and fresh (lime juice at the end). Hitting all of these categories ensures a well-balanced and interesting final product!

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Make It Work for YOU

Good news: chili is a really easy dish to customize in many different ways! You'll see in the ingredient list that I suggest a range of amounts for each spice so that you can choose how spicy you want things and how many other flavors you want to highlight. You can also vary the heat level by using different peppers. I suggest adding a fire-roasted poblano at the beginning and a few fire-roasted bell peppers at the end, but you could easily add in some jalapenos instead of or in addition to the poblano if you like heat, or stick with all bell peppers for no heat.

Additionally, while I suggest butternut squash in this recipe, any winter squash will work great. Just remember to adjust the cooking time accordingly. Kabocha is one of my favorites and would be wonderful here!

Finally, we can all admit that the garnishes and toppings are one of the most fun things about chili, right?? This is a great way to make it your own. I like to have some crunchy garnishes (pepitas, tortilla chips, etc), some fresh ones (cilantro, lime slices), and some creamy ones (e.g. cheese, avocado). And cornbread on the side is always a good idea!

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Make-Ahead Tips

Chili is a make-ahead wonder. It actually gets better over time! If you want to make this ahead of time, which I definitely suggest, you have a couple options:

1. For a partial make-ahead approach, you can cook the wheatberries and roast the squash a day or two before. This will still give you the feel of cooking the chili on the stove all day (which makes the house smell amazing... bonus points if you're having guests!) but will cut out some of the time and dish-washing on the day you're planning to serve it.
2. For a full make-ahead approach, make the whole recipe except for adding the lime juice. When you're ready to serve, just reheat the chili, either in the full batch or in a smaller batch. Add the lime juice right before serving for the best flavor.

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Let's Talk Ingredients

Here's what you'll need for this recipe, as well as some thoughts, tips, and possible substitutions. If you make any substitutions, I'd love to hear about it in the comments section below.

• Wheatberries. Feel free to use farro or barley instead. But if you do, I suggest adding it a bit later in the process so that it doesn't get too soft.
• Cooking oil
• Salt and pepper
• Butternut squash. Or use Kabocha squash or even pumpkin for a different flavor.
• Onions. I love to use sweet onions, since their delicate sweetness helps to balance the spices. But you can use yellow or white onions if you prefer.
• Chili powder
• Cumin powder
• Ancho chili powder
• Whole cumin seeds
• Coriander
• Cinnamon. This definitely isn't a traditional chili ingredient, but I love the warmth it brings to the dish, and it makes so much sense with the squash and pumpkin.
• Ginger powder. Same as above!
• Cayenne pepper
• Poblano peppers. Feel free to use jalapenos instead for additional heat, or just bell peppers for no heat.
• Dash of tequila. Optional but awesome... for deglazing the pot!
• Pumpkin puree. Either canned or homemade is fine. If canned, just make sure it's 100% pumpkin and NOT pumpkin pie filling!
• Black beans
• Corn. Given that chili is usually a winter food and corn isn't in season, I suggest using frozen; it's much better than canned.
• Colored bell peppers
• Lime
• Garnishes of choice. See ideas above. Whatever you love on your chili is great!

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Closing Thoughts

Imagine the most perfect winter Saturday. For me, it involves a long walk outside... and then an afternoon making this chili! We really enjoy the end product, but also the process itself. Cooking a big pot of this chili can really make a winter day feel special! I like to do some of the prep work early, then we listen to some music and sip a couple margaritas while I fire-roast the veggies and do the stove-top work. It's the best sort of date night!

I hope you love this recipe as much as we do. Cheers and happy chili making!

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Share It!

It makes me so happy to hear from you and see your creations! Please leave a comment below and let me know what you think about this recipe. If you post a photo on Instagram, hashtag #TheRogueBrusselSprout and tag me (@TheRogueBrusselSprout) in the post text so that I'm sure to see it.

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Suggested Pairings

Blueberry Ginger Paloma (but with pomegranate instead of blueberries for a wintry feel!)

Grilled Corn Guacamole

Margarita Cauliflower‍

Tri-Colored Citrusy Slaw (the Mexican-inspired version)

Orange Jalapeno Brussel Sprouts