Tender pulled pork simmered in a sweet-spicy chili with caramelized pineapple, pickled jalapeños, and warm spices for a bright, complex warm-weather bowl.
For deeper caramelization, pat the pork shoulder dry before searing and work in batches if needed to avoid crowding the skillet. Pickled jalapeños add both heat and tang; adjust the amount to your spice tolerance. Reserve the brine for extra acidity and flavor.
The chili develops more complex flavor if made a day ahead and reheated. Store in an airtight container in the refrigerator for up to 4 days. Fresh pineapple works best; canned pineapple in juice can be substituted if fresh is unavailable—drain well and reduce the liquid slightly.
Ingredients
Scale
Measurement units
- 3 lb pork shoulder
- 2 cups fresh pineapple
- 1 cup pickled jalapeños (with 2 tbsp of their brine)
- 2 medium onion
- 6 garlic cloves
- 28 oz canned diced tomatoes (one 28 oz can, with juice)
- 3 tbsp tomato paste
- 2 cups beef broth
- 2 tbsp chili powder
- 1 ½ tbsp cumin
- 1 tbsp smoked paprika
- 1 tsp oregano
- 2 tbsp brown sugar
- 2 tbsp lime juice
- 2 tbsp olive oil
- salt (to taste)
- black pepper (to taste)
- ¼ cup cilantro (for garnish)
- lime wedges (for serving)
- sour cream (for serving)
Ingredients
Scale
Measurement units
- 3 lb pork shoulder
- 2 cups fresh pineapple
- 1 cup pickled jalapeños (with 2 tbsp of their brine)
- 2 medium onion
- 6 garlic cloves
- 28 oz canned diced tomatoes (one 28 oz can, with juice)
- 3 tbsp tomato paste
- 2 cups beef broth
- 2 tbsp chili powder
- 1 ½ tbsp cumin
- 1 tbsp smoked paprika
- 1 tsp oregano
- 2 tbsp brown sugar
- 2 tbsp lime juice
- 2 tbsp olive oil
- salt (to taste)
- black pepper (to taste)
- ¼ cup cilantro (for garnish)
- lime wedges (for serving)
- sour cream (for serving)
Instructions
Sear the pork
Heat olive oil (2 tablespoon) in a large skillet over medium-high heat until shimmering.
Pat the pork shoulder (3 pound) dry with paper towels, then season generously with salt and pepper.
Working in two batches if needed, sear the pork until deeply browned on all sides, about 3–4 minutes per side.
Transfer the seared pork to a plate.
Equipment: Large skillet
Caramelize the pineapple and build the base
In the same skillet, add the 2 cups diced pineapple and cook over medium-high heat, stirring occasionally, until the pineapple begins to caramelize and brown at the edges, about 5–6 minutes.
Add the 2 medium diced onions and cook until softened, about 3 minutes.
Stir in the 6 minced garlic cloves and cook for 1 minute until fragrant.
Toast the spices
Add chili powder (2 tablespoon), cumin (1 ½ tablespoon), smoked paprika (1 tablespoon), and oregano (1 teaspoon) to the skillet and stir constantly for 1 minute to bloom the spices.
Stir in tomato paste (3 tablespoon) and cook for 1 minute.
Build the chili in the pot
Transfer the seared pork back to the skillet, then transfer everything to a Dutch oven or large heavy pot.
Add the canned diced tomatoes (28 ounce) with juice, beef broth (2 cup), pickled jalapeños (1 cup) with 2 tbsp of their brine, and brown sugar (2 tablespoon).
Stir well to combine, scraping up any browned bits from the bottom of the pot.
Braise the pork
Bring the chili to a simmer over medium-high heat, then reduce heat to low, cover, and simmer gently for 2 hours, stirring occasionally, until the pork is very tender and shreds easily.
Shred the pork and finish the chili
Remove the pork from the pot using tongs and place on a cutting board. Using two forks or tongs, shred the pork into bite-sized pieces.
Return the shredded pork to the pot and stir well.
Stir in 2 tbsp fresh lime juice and taste for seasoning. Adjust salt and pepper as needed.
Simmer uncovered for 10 minutes to allow flavors to meld.
Equipment: Tongs
Serve
Ladle the chili into bowls and garnish with fresh cilantro if desired. Serve with lime wedges and sour cream on the side.
Before you cook
Cook notes
- • For deeper caramelization, pat the pork shoulder dry before searing and work in batches if needed to avoid crowding the skillet.
- • Pickled jalapeños add both heat and tang; adjust the amount to your spice tolerance. Reserve the brine for extra acidity and flavor.
- • Fresh pineapple works best; canned pineapple in juice can be substituted if fresh is unavailable—drain well and reduce the liquid slightly.
- • The chili develops more complex flavor if made a day ahead and reheated. Store in an airtight container in the refrigerator for up to 4 days.
- • For a thicker chili, simmer uncovered in the final 20 minutes. For a brothier consistency, add 1 cup more beef broth before simmering.
- • Lime juice brightens the sweet-spicy balance; add it at the end of cooking and taste before serving.
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