Crock-Pot Crazy Pineapple Chili
~ Contest-winning chili with an amazing flavor twist that people go crazy over! Quick and easy in the slow cooker – and healthy, too! A guaranteed win! ~
This Recipe Is: • Freezable • Make Ahead • Gluten Free •
It may be a little crazy, but this chili doesn’t mess around!
It’s a mega-award winner, one chili cook-off after another.
Not those national kind of cook-offs where professional contest-entering-folks compete to see who can concoct the most bizarre kluge of unrelated ingredients.
Nope! This one wins all those neighborhood and workplace contests. You know – the cook-offs where real people enter the really-truly-best chili they’ve ever tasted, the recipe they always, always make. And you just know that to win those contests, it’s gotta be really, truly good.
Crazy? Yep!
Really and truly good? You betcha!
Oh, sure – I know the pineapple has you kinda scratching your head. Huh? Pineapple? In chili???
You’re intrigued but a little wary, right? I understand! I’ve been there!
I first heard the legend of Crazy Pineapple Chili from my dear, dear friend Sue. She’s a former children’s librarian who is now a stay-at-home mom and volunteer for practically anything you can imagine. She’s incredibly creative and pretty much does everything with a wonderful, unmistakable flourish.
A few years back, she decided to host a bash for some of her family and friends. Fun! Of course, it could be no ordinary party. Sue decreed that it would be a chili cook-off. Double-fun!
Weeks ahead of the party she whispered to me news of a special entry … the legendary Crazy Pineapple Chili from her brother-in-law, Gary. Sue reported that this chili had won all manner of cook-offs and friendly little competitions.
I anxiously awaited my meeting with this chili for weeks. I wasn’t disappointed.
IT WAS AMAZING! (Oh – and Sue’s bash was fab, too, of course! 😀 )
But really … this chili …
Despite there being some other great chilis at Sue’s party that night, this uniquely delicious chili certainly won the day. Hands-down, over-the-top, exceeding-my-expectations.
It’s rich and tomato-y, with wonderful flavor from Italian sausage (surprise again – no ordinary hamburger in this chili, my friends!). And then the pineapple … so, so good. It lends a warm, luscious sweetness that perfectly counterpoints the savory and spicy notes.
It’s an epiphany in a bowl.
Crazy-fantastic.
Since Sue’s party, it’s gone on to win again, as expected. Most recently, it won my neighborhood’s chili cook-off. I was so bummed that my family had a conflict (ummmm … too many soccer games … you know). ‘Cause you know what chili I wanted to make, right?!?! But then I was thrilled to hear that this chili DID make an appearance (and won the grand prize, none-the-less)! It was entered by another dear friend, Lisa, who’s also been head-over-heels in love with it ever since Sue’s party!
You see what I mean. It kinda develops a loyal following.
Know what you’re gonna love even more than how great it tastes, though?
IT’S SO EASY!
We’re talking crock-pot cookin’, my friends! You can even cook the sausage and onions the night before and refrigerate, so it’s extra-quick to throw everything together in your slow cooker in the morning. Or, you can make the chili ahead and freeze it in batches. So simple!
Now as you would absolutely expect from THK, we tinkered with Gary’s recipe a little. Because it wasn’t amazing? No … it’s all kinds of amazing, for sure. We made just a few adjustments to quell the heat a bit for the kiddos (but don’t worry – our recipe card has suggestions for amping the heat right on back up!).
We also slashed some of the fat. A simple swap that no one will ever notice is using Italian turkey sausage instead of regular, full-fat Italian pork sausage.
Next, we traded out some of the sausage for black beans. They add great texture and loads of nutritional benefits.
Not a bean fan? Or maybe you live in Texas, where putting beans in chili is practically a jailable offense? No worries – you can leave those beans out altogether or even swap back in a bit more sausage, just like in Gary’s original recipe.
Here at THK, we’ve made it both ways and can never get people to agree on the beans vs. no beans debate. But then, that’s pretty much the story of all chilis – the beans are always the conundrum.
So make it our way … make it your way … make it any way. You’d be CRAZY not to!
Crock-Pot Crazy Pineapple Chili
Contest-winning chili with an amazing flavor twist that people go crazy over! Quick and easy in the slow cooker – and healthy, too! Keep it on the mild, slightly sweet side, or use our tips to spice it up!
• Freezable • Make Ahead • Gluten Free •
Ingredients
- 20 ounces sweet Italian turkey sausage (bulk, or links with casings removed)
- 1 medium onion, chopped to equal about 2 cups
- 1 (20-ounce) can pineapple tidbits in juice (divided)
- 2 (28-ounce) cans seasoned diced tomatoes (such as Dei Fratelli)
- 1 (15-ounce) can black beans, rinsed and drained
- 1 (6-ounce) can tomato paste
- 1 1/2 tablespoons chili powder
- 4 teaspoons ground cumin
- 2 cloves garlic, minced
- shredded reduced-fat cheese, reduced-fat sour cream and hot sauce (such as Tapatío) for serving, if desired
Instructions
- In a non-stick skillet over medium heat, cook sausage and onions, stirring to crumble sausage. Once sausage is cooked through, drain off any fat and transfer the sausage and onions to your slow cooker.
- Drain the pineapple, reserving both the juice and the fruit separately. Add the juice to the slow cooker. Cover and store the fruit in the refrigerator (it will be added toward the end of cooking).
- Add tomatoes, black beans, tomato paste, chili powder, cumin and garlic to the slow cooker.
- Stir everything to combine.
- Cook on low (6-8 hours), adding reserved pineapple during last hour or two of cooking, or on high (4-5 hours), adding pineapple during last 1/2 hour - hour of cooking.
- Serve topped with cheese, sour cream and hot sauce, if desired.
Notes
Pineapple: The texture of the cooked pineapple is completely controlled by when you add it. We prefer to add it toward the end of the cooking time, so that it's still fairly firm. If you prefer it to be more melded into the chili or you simply won't be able to add it toward the end of cooking, then you can toss it in at the beginning – it will be cooked down and much less pronounced in texture, but still very good.
Beans or no beans: If you don't want beans in your chili, you may certainly leave them out, and can also increase the amount of meat. We love the texture and the health benefits of the beans, but feel free to try it different ways!
Spice: This recipe is intentionally fairly mild and kid-friendly. If you'd like more spice, you can increase the chili powder and/or sub in spicy Italian turkey sausage. Perhaps the best way to make it versatile for different pallets, though, is simply to pass hot sauce at the table so everyone can season to taste.
Make-ahead: You can prepare the meat and onions the evening before, and then refrigerate until you assemble your ingredients in the slow cooker. You can also make the chili entirely in advance and freeze it in large batches.
Nutrition Information:
Yield: 10 servings Serving Size: 1 cupAmount Per Serving: Calories: 469Total Fat: 8gSaturated Fat: 1gTrans Fat: 0gUnsaturated Fat: 4gSodium: 626mgFiber: 15gProtein: 22g
Nutrition information should be considered an estimate only, and may vary depending on your choice of ingredients or preparation. No guarantees are made regarding allergies or dietary needs. Always consult a physician or dietician for specific advice and questions.
I love pineapple on my pizza! So why not in chili! Sounds rockin! Perfect for a Super Bowl Party too!
Oh yeah! Perfect for a Super Bowl party! Any party actually – it’s great to feed a crowd! Just last weekend, I’d made a double batch ahead of time and frozen it all, then served it at my kiddos’ big family birthday party (they’re twins … so … same b-day!). Anyway, it was a smash hit, as always – perfect party food for a big group! 😀 ~Shelley
What a great idea! Love pineapple and the thought of it in chili makes my mouth water!
Yeah – this is seriously good stuff! As soon as you taste the pineapple in this chili, it’s one of those eureka moments when you wonder why you never tried this before! Well … after the first time you make it, it definitely won’t be the last! Enjoy! 😀 ~G&S
This looks incredible Shelley! I love chili, especially when it’s a crockpot recipe! That pineapple addition is brilliant! And I love that you subbed in turkey sausage. Fantastic recipe!
Thanks so much, Taylor! The slow cooker makes it incredibly easy, and it gives the flavors a chance to meld beautifully! I think you’ll be surprised at how gorgeous the flavors of pineapple and sausage are together, along with the other typical chili flavors. Yum! 😀 ~Shelley
As you know, one of my family favs! I use hot Mexican chili powder and half of my sausage is hot/spicy. The result? It’s zippy without being too spicy. Hope everyone enjoys!
Hey, Lisa (aka The Neighborhood Chili Cook-Off Winner! :D)! Thanks for the tips on how you spice up your version! Three out of the four of us in my family would love the extra heat, but keeping it milder means that I win with FOUR out of the four of us! We just keep that Tapatío handy! So … at the next Neighborhood Chili Cook-Off … I guess you, Sue and I will all have to duke it out for who gets to bring the Crazy Pineapple Chili! Lol! Hugs … ~Shelley
Consider this pinned! Pineapple sounds like a great addition to my next pot of chili! Thanks, ladies. And love the fact you have lots of beans in this for all the fiber and other health benefits.
Thanks, Lori! It really is so awesome – the pineapple is such a unique and delicious twist! People are really surprised by how much they love it! And yes – you know Gretchen and I are all about the healthy addition of the beans! Happily, even for people who don’t want to include the beans, this chili is still brimming with leaner meat, and loads of nutritional goodies from the onions, all those tomatoes, and the scrumptious pineapple! 😀 ~Shelley
I’m entering this in a work contest tomorrow but stressing out about it since I’ve never made it before. Would the pineapple stay good texture if I cook it tonight and then have it simmering tomorrow during the day? People stop in and graze throughout the day.
Hi, Kerry! I think that the pineapple should hold up just fine.:) It will probably start to break down a bit by the end of the work day — but not so much that it won’t still be tasty! We — and many of our readers — have been bringing this to chili cook-offs for years, and have never had a major problem with the texture — even after it’s been simmering for a few hours. It may change a bit throughout the day, but again, it shouldn’t be a problem. If you’re worried, I would suggest adding the pineapple in even later than the 30 minutes-hour we recommend in the recipe — maybe pop it in just before you leave for work tomorrow.
Hope that’s helpful — and good luck tomorrow! 😀 ~Amy