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 tried your recipe —- and —- it’s tasty! Since we’ve had the original, we can make the comparison, and both Scott and I agree that your version tastes like Gary’s. I would add that it tastes lighter. Maybe that’s a strange adjective, but I think the turkey sausage lightens the chili up and prevents those “chili burps” later in the evening (LOL)! I have never used turkey sausage before, so thank you for the introduction. Your recipe is super-easy to make, and while Gary and my sister, Karen, pronounce that crazy pineapple chili should not contain beans, my family liked the addition. 🙂
Hi, Sue! We’re thrilled to have your expert feedback! Now, I have to admit that, knowing how Karen hates beans in her chili (which is kinda the whole reason Gary developed a bean-free chili for her in the first place), I knew they would be sticking to their guns and going with the beanless version! Perfect example of why we still included the beanless option (well, and for our Texan THK fans, too …). But, I’m so excited to hear how much you and Scott and your kiddos enjoyed our lighter version … and that you think it still retains the original flavor! That’s a huge compliment, and I’m so happy you took a moment to give us your feedback! Oh, and getting rid of those chili burps (total LOL :D)? You’re welcome! ~Shelley
Pineapple.. in chili?? Really?? Haha I’m beyond intrigued by this and now I HAVE to test this out.
Hi, Christine! Great timing on your comment, since I know you’re a vegan blogger! As I actually just mentioned in my reply comment to Kelly below (great minds must definitely think alike!), I do absolutely think that you could easily make a vegan (or vegetarian) version of this, as well. I’ve never tried it with this specific recipe, but I do think it would work. So glad you’re intrigued (I sure was when I first heard about it!) … hope you give it a go! 😀 ~Shelley
You know, I had pineapple in a vegan chili one time, and I was surprised at how much I liked it! Your recipe sounds delish! 🙂
Thanks, Kelly! I’m sure you could vegan-ize this chili with vegan-friendly sausage or veggie crumbles. I actually love veggie crumbles (and use them often in a veggie soup we’re posting this fall), but I’ve never tried them specifically in this chili. I think they’d work just fine, though. You could also try simply leaving out the meat altogether and increasing the amount of beans (maybe use a second type of beans such as red kidney or cannellini for variety). Regardless, you’ll want to adjust the seasonings a bit to account for the fact that you’ve lost the Italian spices inherent in the sweet Italian sausage my version calls for. I would love to know how it goes if you try it! 😀 ~Shelley
Yes, pineapple in chili…sounds delicious, I love the idea of sweet and tart flavors in chili…nice twist.
Thanks for the recipe and hope you are having a wonderful week 😀
The flavor combination really is fabulous, and yes – such a wonderful twist! Hope you’re having a great week, too! ~G&S
Guess what I’m making TODAY on this cold weather calamity day off of school? Can’t wait to try it. Jen O. has won the EW Chili cook off 4 yrs in a row. I’m hoping to give her a run for her money. Miss you both tremendously!! Hugs to the kids from me.
You are most definitely going to reign supreme in the EW Chili Cook-Off this year … especially if you’ve got that sweet little helper on your side! 🙂 Oh! Maybe even make double batch and freeze some for those hectic evenings!
Hmmmm … Do you happen to need taste-testers for this competition? We may be able to assist!
Stay warm – looks like more cold to come! Hugs to you! ~G&S