Cut the pork shoulder into bite-size pieces and season them generously with salt & pepper.
Heat 1 TBSP of the oil in a large saute pan or dutch oven over medium-high heat. Sear half the pork until browned on all sides, about 6 minutes. Transfer the seared pork to a 6-quart slow cooker. Add the remaining 1 TBSP of oil to the pan and sear the remaining pork then transfer it to the slow cooker as well.
Keep the pan over medium-high heat and add the onion, tomatoes, and vinegar. Cook while using a wooden spoon or spatula to scrape the bottom of the pan to release any stuck on bits, for about 1 minute then pour the contents of the pan into the slow cooker with the pork.
Stir the black beans, jalapeno, paprika, cumin, garlic, water, and 1/4 tsp salt into the slow cooker until everything is well combined.
Place the lid on the slow cooker and cook on LOW for 7 to 8 hours or until pork and beans are tender.
Stir the chili and season with additional salt & pepper to taste.
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