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Boil Water: Bring 4 cups of water to a boil in a medium size pot.
Remove Seeds Use a sharp knife to cut off the stem of the peppers, remove the seeds.
Toast: Heat a cast iron skillet over medium heat and add the peppers, cook 2-3 minutes just to toast them.
Soak: Remove the boiling water from the heat, add the peppers to the boiling water, cover the pot with a lid and let the peppers soak in the hot water for 30 mins
After soaking, remove the peppers from the water to a cutting board. They should be nice and soft and not hot to the touch. (RESERVE THE WATER FROM SOAKING THE PEPPERS)
Remove the skins from the peppers: Easiest way is to slice the peppers in half, lay them flat skin side down and gently scrape the flesh of the pepper off of the skin. The peppers will be mostly mashed by this point, just give a few chops to the peppers to ensure they are nice and mashed, almost like a paste.
Trim: Remove all excess fat from the meat—just large chunks of fat, not marbling (too much fat will make the chili greasy)
Chop: Cut the meat into 1 inch cubes.
Sear: Working in batches, cook the meat in a large dutch oven or iron pot over medium heat. Sear the meat on all sides, once seared, remove the meat to a plate and continue until all meat is cooked. (I never have any issues not using any oil for this step..again it cuts down the grease in the chili. Just be sure to turn the meat often while cooking to prevent sticking or bits burning in the pot.)
After all the meat is cooked and on the plate, saute the garlic in the pot for about 30 seconds.
Deglaze: Pour 2 cups of the reserved chili water (from soaking the peppers) into the pot. Stir and scrape the bottom of the pot with a wooden spoon to loosen any bits stuck to the pan.
Stir in the mashed chili peppers until mixture is smooth.
Add the meat into the pot. Add additional chili water, just enough to cover the meat. (Start with less liquid than you think.. you can always add more as it cooks, the goal is to not make it too liquid-y) If needed you can use beef broth if you run out of chili water.
Bring to simmer, then reduce heat to low. Cover and let cook for 30 mins.
Spice Dump: After simmering for 30 minutes, uncover and stir in the oregano, cumin, and salt. Check liquid levels, add additional chili water/beef broth as needed to keep the meat covered in liquid.
Bring back to a simmer, lower heat, cover and let cook for 45 minutes. Keep stirring limited during this time to help prevent meat from breaking apart.
Seasoning: After simmering 45 minutes, uncover, skim any grease off of the top. Test the flavoring and adjust as needed (additional salt, chili powder for more heat, etc.) Add additional liquid if needed.
Thicken: In a small bowl add 2 tbsp of masa, pour in 1/4 cup of the broth from the chili. Whisk this together, then pour this into the pot of chili. The masa will help thicken the chili and bind it all together.
Bring to a simmer, lower heat, cover and let simmer a final 30 minutes.
Serve bowls of chili topped with diced onion and shredded cheddar cheese, or additional toppings if desired!