Spicy Beef Chili with Butternut Squash and Black Beans

Back where I come from, chili seems to come in just one form – the standard ground beef and kidney beans, and when we make it, we make it big. When you’re only feeding two people, a batch of chili becomes a week-long dinner commitment with extra in the freezer. In fact, the last pot I made, about two years ago, lasted until I never wanted to see chili again. Not being a huge leftover enthusiast, I somewhat lost my taste for it altogether.

chili1 Spicy Beef Chili with Butternut Squash and Black Beans

That being said, I have always been intrigued by the “other” chilis – the ones with pinto beans, black beans, squash, chunks of beef, tomatillos, hominy (which still remains a mystery to me – kinda looks like rubber popcorn), etc.

This version knocked the ball out of the park, and definitely redeemed chili in my books. Not for the faint of heart, this meaty, rich, spicy chili is man’s food, comfort food, and perfect Fall food, all in one delicious bowlful. The meat becomes so tender it falls apart with the slightest encouragement from your spoon. The long-cooked onions and generous dose of garlic make a rich, flavorful base. (Don’t skip out on the long saute time for the onions, or on browning the beef. The depth of flavor those steps add is incredible). I used two jalapeno peppers, seeds ‘n all, and it definitely cleared the sinuses. Use one jalapeno, and/or remove the seeds for less heat. If you are unsure, always best to err on the side of milder than to make it too hot. However, if you do give it more kick than you intended, all is forgiven with a big spoonful of rich sour cream to perfectly temper the heat.

chili2 Spicy Beef Chili with Butternut Squash and Black Beans

When I made it, I put the squash and the beans in the pot with the beef from the beginning. After a couple hours at a simmer, both had essentially broken down into the sauce. I amended my recipe by calling for the beef to be simmered alone for an hour first before the beans and squash are added. This should make it pretty much perfect.

Here it is, my answer to an afternoon of chasing a bouncy dog around the beach in the rain, or a long walk in the autumn woods, or just about any day that should conclude with a bowl of hot comfort food.

Spicy Beef Chili with Butternut Squash and Black Beans

  • 3 lbs stewing beef, chunks
  • 1/2 cup olive oil, divided
  • 2 medium onions, diced
  • 4 cloves garlic, minced
  • 4 cups canned, diced tomatoes (2 14.5 oz cans)
  • 4 tbsp tomato paste (1/2 of a 6 oz can)
  • 1 tbsp cumin
  • 2 tbsp mexican chili powder
  • 2 tbsp brown sugar
  • 1-2 jalapeno peppers, diced
  • 2 cups cubed butternut squash (about half a medium squash)
  • 2 cups cooked black beans (1 can)
  • salt and pepper
  • sour cream, grated cheddar cheese, green onions to serve, optional

1. Pat the beef dry with paper towels and season with salt and pepper. Heat 2 tbsp olive oil over medium-high heat in a dutch oven or heavy pot. Add beef in a single layer on the bottom (you will need to do 2 batches) and cook until browned on all sides. Transfer beef to a bowl, and set aside, and repeat with second batch adding another 2 tbsp oil to the pot.

2. Heat remaining 1/4 cup oil in the same pot used to brown the beef. Add onions and cook over medium heat until very golden, about 10 minutes, stirring occasionally. Add garlic and saute 2 minutes. Add jalapeno, tomatoes, tomato paste, cumin and chili powder. Season to taste. Return beef to pot. Bring to a boil, then reduce to a simmer and cook, covered, 45 minutes to 1 hour.

3. Add butternut squash and black beans. Continue to simmer another hour, or until beef is very tender and squash is cooked through.


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  1. Shawn Taylor

    September 29, 2010 8:27 am - Reply

    Oh my god… This is why I love winter. I am making right away. Sounds so good!!!

  2. Claire Osborne

    November 11, 2010 2:02 am - Reply

    Foodess, this stew is amazing! The smell while the onion was cooking for a good ten minutes was mouth watering and definitely worth the wait. While this chilli was amazing the first night, after a night of sitting in it’s own juices overnight, the richness of flavour the next day was incredible! Also, i used one de-seeded jalapeno pepper and one teaspoon of chilli as my tastebuds are pretty pathetic when it comes to chilli, and it gave the stew a very mild warmth. Next time i think i’ll add more of these two hot ingredients to kick it along. Yet another masterpiece! Highly recommended!!

    • Anonymous

      November 11, 2010 6:23 am - Reply

      Thanks Claire!! Glad you enjoyed! :-)

  3. Mathilde

    December 5, 2010 11:08 am - Reply

    Jennifer, I’ve tried your chili a few days ago and it was delicious! This blog is simply amazing.

    • Anonymous

      December 6, 2010 5:58 pm - Reply

      Merci Mathilde! I’m glad you liked the chili!!

  4. Christine

    December 4, 2011 2:02 am - Reply

    Just made this tonight, delish! Definitely a keeper!

  5. Kaye Kaye

    October 27, 2013 8:33 pm - Reply

    Thank you soooooo much for your blog!! You have no idea how much I enjoy your recipes and they are so easy to follow. I have never cooked with butternut squash. Do I peel the squash or leave the skin in place.

    • foodess

      October 28, 2013 5:20 pm - Reply

      Thank you for your lovely message, Kaye! You do peel the squash – a veggie peeler works great on the thin butternut squash skin :)