Part 1: Preparing the Chile Paste

1. Toast the Chiles: Place a dry, heavy-bottomed skillet or comal over medium heat. Working in batches, press the dried chiles flat onto the hot surface for about 20-30 seconds per side. You’ll know they’re ready when they become fragrant and slightly more pliable. Be very careful not to burn them, as this will make them bitter.
2. Stem and Seed: Once the chiles are cool enough to handle, snap off the stems and shake out as many of the seeds as you can. A few remaining seeds are fine.
3. Rehydrate the Chiles: Place the toasted and de-seeded chiles in a heatproof bowl. Pour 4 cups of very hot (but not boiling) broth or water over them. Use a small plate or bowl to weigh them down, ensuring they are fully submerged. Let them soak for at least 30 minutes, or until they are very soft and pliable.
4. Blend into a Paste: Transfer the softened chiles and about 1 cup of their soaking liquid to a high-powered blender. Blend on high speed until you have a completely smooth, deep red paste. If it’s too thick, add more of the soaking liquid, a tablespoon at a time, until it reaches a thick but pourable consistency. Strain the paste through a fine-mesh sieve, using a spatula to press all the liquid through. This step is crucial for a silky-smooth texture. Discard the solids left in the sieve. Your chile paste is now ready.

Part 2: Cooking the Chili

1. Prepare the Beef: Pat the cubes of beef chuck completely dry with paper towels. This is essential for getting a good sear. Season them generously on all sides with salt and pepper.
2. Sear the Beef: Heat the oil or lard in a large, heavy-bottomed pot or Dutch oven over medium-high heat until it shimmers. Working in batches to avoid overcrowding the pan, add the beef cubes in a single layer. Sear them on all sides until a deep, brown crust forms. Do not rush this step; the fond (the browned bits left in the pan) is the foundation of the chili’s flavor. As each batch is browned, use a slotted spoon to transfer it to a separate bowl.
3. Sauté the Aromatics: Reduce the heat to medium. Add the chopped onions to the same pot, scraping up any browned bits from the bottom. Cook, stirring occasionally, for 8-10 minutes, until the onions are soft and translucent. Add the minced garlic, ground cumin, and dried oregano. Cook for another minute, stirring constantly, until the spices are very fragrant.
4. Deglaze the Pan: Pour in the dark beer to deglaze the pan. Use a wooden spoon to scrape up any remaining stubborn browned bits from the bottom of the pot. Let the beer simmer and reduce by about half, which should take about 5 minutes.
5. Combine and Simmer: Return the seared beef and any accumulated juices back to the pot. Pour in the prepared chile paste and enough additional broth to just cover the meat. Stir everything together to combine. Bring the mixture to a strong simmer.
6. The Low and Slow Cook: Once simmering, reduce the heat to the lowest possible setting. Cover the pot and let it cook for at least 3 hours, or up to 4 hours. Stir it every 30-45 minutes to prevent scorching at the bottom. The goal is for the beef to become incredibly tender and for the flavors to meld and deepen.
7. Thicken and Finish: After 3 hours, check the chili. The beef should be fall-apart tender. In a small bowl, whisk the Masa Harina with 1/4 cup of cool water to create a slurry. Stir this slurry into the chili. This will thicken the sauce and add a subtle, authentic corn flavor. Let the chili simmer, uncovered, for another 15-20 minutes to allow the sauce to thicken.
8. Final Seasoning: Taste the chili. This is where you adjust it to your preference. Add salt and pepper as needed. If the chili tastes slightly bitter from the chiles, a tablespoon or two of brown sugar can balance it out. If the flavor feels a little flat or heavy, a splash of apple cider vinegar can brighten everything up.
9. Rest: For the absolute best flavor, turn off the heat, let the chili cool, and refrigerate it overnight. The flavors will continue to meld and deepen, resulting in an even more complex and delicious dish the next day. Reheat it gently on the stove before serving.