This was the third year for the annual chili cookoff at my office. I won the 1st year, I was home sick the 2nd year year, and this year I reclaimed the trophy. This chili turned out just as I wanted it – thick, rich, smokey, sweet, spicy, and is very comforting just as chili should be. Oh, and did I mention – I WON the cookoff? 🙂
And this is what happens when you work in a field with graphic designers who are skilled at photoshop: My winners’ portrait. HA!
I wanted to do something unique and different for my entry this year. I love surprising people with ingredients that they think ‘just don’t belong’, but it was important to keep the beloved flavors of chili. I thought of using pineapple since my favorite pizza combo is jalapeño, pineapple & pepperoni. By using pineapple, I could balance the heat with the sweet pineapple, and since I love el pastor style street tacos, I decided to do a pork & pineapple based chili.
Now, this chili is a serious endeavor mostly because of the kalua pork I used here. You will see me use this a lot in my blog posts as its delicious, and when you make it you have a large quantity to use across a few dishes. Now, you can use whatever type of pork you want: ground, cubed, roasted, etc. – but if you follow my recipe 100%, you need to roast your pork before you start the chili – which takes approx 10 hours in a crockpot. Recipe here.
Be sure to do all the work below a day ahead. You want the chili so sit overnight so the flavors meld before you reheat and serve. So, if you decide to do the kahlua pork in the crockpot I suggest you set the pork in the crockpot in the morning, come home that evening to start the steps below, and then put all in fridge overnight.
Here’s the recipe!
- 28 oz + 14 oz can of diced tomatoes
- 1 small can (6 ox) tomato paste
- 1 pineapple cored and cut into spears
- 1 small can crushed pineapple (8oz)
- 1/3 lb thick cut bacon diced
- 2 lb beef chuck roast cut into very small cubes
- 2 lbs pulled kalua pork
- You can use ground or very small cubed pork shoulder as substitute
- 1 large onion diced
- 5 large cloves of garlic minced
- 2 cans black beans – rinsed and drained
- 5 tsp oregano
- 5 tsp ground cumin
- 1 tbsp paprika
- 2 teaspoon cayenne pepper
- 1/4 cup + 3 tbsp of chili powder
- 3 teaspoon salt
- 1/2 of small can of chiles in adobo sauce (approx 4 peppers w/ the sauce)
- Pinch red pepper flakes
- 1 tbsp diced pickled jalapeño
- 1 tbsp pickled jalapeño juice
- 1/3 cup brown sugar
- 2 tbsp honey
- 2 cups water
- 1 cup chicken stock
Optional ingredients (but recommended)
- shredded white cheddar
- cilantro leaves
- Turn oven to high boril or turn on grill
- Toss pineapple spears in pinch of chili flakes and 1 tbsp of the chili powder
- Place pineapple on grill or on foil in oven on broil or grill. Turn pineapple so all sides are black/charred on the edges: About 8-10 minutes on each side.
- Set one spear aside and dice the other spears into small pieces – set aside.
- In a food processor, puree the adobo chiles and the one spear of the pineapple until smooth puree is formed. Set aside.
- Find a large pot (large enough for all of this chili which filled my BIG crockpot) – IE: big heavy bottomed pot or dutch oven.
- In the large pot over medium high heat, cook bacon until it is mostly brown, but not crispy yet. Remove with slotted spoon and lay on paper towels to cool.
- Pour off most of grease into a glass bowl or container and set aside. Leave about 1 tbsp in pan.
- Add beef to the pot. Be sure to only add enough to cover the bottom, do not crowd the pan. If too much beef for one round of cooking – do in batches and use the bacon grease to cook the beef.
- Once browned on all sides, remove beef and set aside in bowl, Reserve juices with the meat.
- If using kalua pork it is already cooked, but if you choose to cook ground pork or cubed pork shoulder, cook it now in the same fashion you did the beef. Set aside once done.
- All meat is cooked, and now its time to get this chili moving!
- To the pot add 1 tbsp of bacon grease, and then over medium heat, cook the onion until shiny and soft.
- Add garlic to the pan and cook for approximately 3 minutes.
- Add the chipotle/adobo/pineapple puree and the tomato paste to the pan – cook for approximately 2 minutes.
- Add the cumin, oregano, chili powder, paprika, salt, and cayenne pepper and continue to cook for about 2 minutes.
- Add in all the diced tomatoes, the bacon, the beef, the jalapeños, the jalapeño juice, brown sugar, honey, the water and chicken stock (not the pork, pineapple or beans yet)
- Bring to a simmer and continue to stir. Let simmer for approximately 5 minutes.
- Add pineapple, beans, & pork to the pot. Return to simmer and allow to simmer for approximately 2.5 to 3 hours. Stirring every 30 minutes or so.
- Once finished cooking, remove from heat and let cool for about 30min. Place into fridge overnight.
- Remove from fridge, bring to simmer and taste. If too spicy, use the canned pineapple to bring the spice down. I added the whole can the next morning as mine was very spicy. However this is a last minute step so you can control the heat and attempt to tone it down if needed.
- Serve with white cheddar and topped with cilantro – very delicious and pairs well with the sweet spice.
|Step 2: Tossing pineapple in chili powder & red pepper flakes|
|Step 3: Broiling pineapple|
|Step 5: puree of chipotle & pineapple|