Servings: 8 to 10

Chili Paste: subheading: Chili Paste:
3 whole ancho, pasilla, or mulato chilies (seeded and torn into 1 inch pieces) 3 whole ancho, pasilla, or mulato chilies (seeded and torn into 1 inch pieces)
2 whole New Mexico Red, California, costeno, or choricero chilies (seeded & torn) 2 whole New Mexico Red, California, costeno, or choricero chilies (seeded & torn)
1 whole cascabel, arbol, or pequin chili (seeded & torn) 1 whole cascabel, arbol, or pequin chili (seeded & torn)
 
Alternate dried Chilies (Babish): subheading: Alternate dried Chilies (Babish):
2 pasilla chiles 2 pasilla chiles
4 arbol chiles 4 arbol chiles
4 chipotle chiles 4 chipotle chiles
3 guajillo chiles 3 guajillo chiles
3 ancho chiles 3 ancho chiles
 
Alternate Chilies (different Kenji Recipe) *this is what I go with: subheading: Alternate Chilies (different Kenji Recipe) *this is what I go with:
3 New Mexico (Red or Green) 3 New Mexico (Red or Green)
2 Arbol or Cascabel Chilies (hot) 2 Arbol or Cascabel Chilies (hot)
3 Ancho (or Pasilla) 3 Ancho (or Pasilla)
2 Chipotle Chilies (in sauce) de-stemmed and seeded plus 2 tbs of sauce 2 Chipotle Chilies (in sauce) de-stemmed and seeded plus 2 tbs of sauce
 
Other chili paste ingredients: subheading: Other chili paste ingredients:
1 1/2 tablespoons whole cumin seeds, toasted and ground 1 ½ tablespoons whole cumin seeds, toasted and ground
1 1/2 teaspoons whole coriander seeds, toasted, then ground 1 ½ teaspoons whole coriander seeds, toasted, then ground
1 whole cloves, toasted and ground (original calls for 2?) 1 whole cloves, toasted and ground (original calls for 2?)
1 teaspoon fish sauce 1 teaspoon fish sauce
1 teaspoons soy sauce 1 teaspoons soy sauce
2 tablespoons tomato paste 2 tablespoons tomato paste
1 cup chicken broth (or water) 1 cup chicken broth (or water)
 
Chili Ingredients (not in the paste): subheading: Chili Ingredients (not in the paste):
2.5-3 pounds boneless chuck roast, trimmed of excess fat 2.5 to 3 pounds boneless chuck roast, trimmed of excess fat
2 tablespoons vegetable oil 2 tablespoons vegetable oil
1 large yellow onion, diced (about 1 1/2 cups) 1 large yellow onion, diced (about 1 ½ cups)
4 cloves garlic, minced (about 1 tablespoon) 4 cloves garlic, minced (about 1 tablespoon)
1 tablespoon dried oregano leaves 1 tablespoon dried oregano leaves
1 cup low sodium chicken broth 1 cup low sodium chicken broth
2 (15 oz) cans kidney beans, drained and rinsed 2 (15 oz) cans kidney beans, drained and rinsed
2 bay leaves 2 bay leaves
1 (28-ounce; 794g) can diced tomatoes (or crushed for a more pasty chili) 1 (28-ounce; 794g) can diced tomatoes (or crushed for a more pasty chili)
1/4 cup (60ml) cider vinegar, plus more to taste ¼ cup (60ml) cider vinegar, plus more to taste
 
Optional Additions: subheading: Optional Additions:
3 fresh Thai bird chilies or 1 jalapeño, finely chopped 3 fresh Thai bird chilies or 1 jalapeño, finely chopped
1 poblano pepper 1 poblano pepper
1 red bell pepper 1 red bell pepper
1/4 cup diced pickled jalapeños ¼ cup diced pickled jalapeños
1/4 cup (60ml) vodka or bourbon ¼ cup (60ml) vodka or bourbon
1 tablespoon (15ml) Buffalo-style hot sauce, such as Frank's RedHot (or more to taste) 1 tablespoon (15ml) Buffalo-style hot sauce, such as Frank's RedHot (or more to taste)
2 tablespoons dark brown sugar 2 tablespoons dark brown sugar
1 tablespoon extra-finely ground coffee beans 1 tablespoon extra-finely ground coffee beans
1 ounce chopped unsweetened chocolate (or 2 tsp cocoa powder) 1 ounce chopped unsweetened chocolate (or 2 tsp cocoa powder)

Chili Paste: subheading: Chili Paste:
Get at least 2 to 3 cups water boiling (in a kettle is easy). Add dried chilies to a large heavy-bottomed sauté pan and cook over medium-high heat, stirring frequently, until slightly darkened with an intense, roasted aroma, 1 to 2 minutes. Do not allow to smoke.
Add the toasted chilies to a bowl and fill the bowl with the boiling water until they're covered. Cover the bowl and let that sit for 15 to 30 minutes. Peppers should be rehydrated and not leathery.
===OLD/ALTERNATE=== Add 1 cup of chicken stock (or water) and cook for 5 to 8 minutes, keeping the liquid at a bare simmer or slightly under. Do not simmer or boil the chilies, as they will become horribly bitter.
Add the whole spices to a pan and toast them for 30 seconds or so (until fragrant) before removing them and grinding them to dust. Do not over-toast or they will become bitter.
Transfer chilies and liquid to a blender. I usually discard the soaking liquid as it's pretty bitter. Adjust the thickness to your preference with chicken stock. Add fish sauce, soy sauce, tomato paste, ground spices, coffee (optional), and chocolate (optional) and blend at high speed, scraping down sides as necessary, until a completely smooth purée has formed, about 2 minutes. Set aside.
Chili Pre-cooking: subheading: Chili Pre-cooking:
Note: It's important to have everything else prepped/measured/opened at this point, because stuff is going to go relatively fast from here.
Season the roast meat on all sides with salt and pepper. Add oil to pan and heat over high heat until smoking. Add roast to the pan, getting a deep brown sear on all sides, reducing heat if fat begins to smoke excessively or meat begins to burn. Let cool at room temperature.
Lower the heat to medium and drain all but 2 tbs oil. Add the onions and fresh peppers. and cook the onions until soft but not browned. Scrape the fond off the bottom of the pan while cooking the onions. The liquid from the onions should be enough to loosen it.
Add fresh hot chilies (optional), garlic, and oregano and cook until fragrant, about 1 minute. Add chili paste and cook until it just starts to stick to the pan. Pour the whole pan into the crock pot.
Add the can of diced tomatoes to the pan and use it to deglaze any stuck-on chili paste. Add it to the crock pot once everything has been scraped off. Add the cider vinegar and beans to the crock pot with it.
The meat should be cool enough to handle. Cut it into ½ inch cubes (or whatever size/variation of sizes you want and add to the crock pot. Stir everything up and if it needs to be thinned out any, thin out with chicken stock. *Note - it will thin itself a bit during cooking as everything releases their juices.
Add the bay leaves and cover them with some chili. Cook and cover until beef is tender and chili is thick, 8 hours on low, 6 hours on high. Do the _finishing_ step 30 minutes before the chili is done cooking.
Finishing: subheading: Finishing:
Remove and discard bay leaves. Add vodka (or bourbon), hot sauce, brown sugar, and pickled jalepenos and stir to combine. Season to taste with kosher salt, ground black pepper, and additional vinegar.

This recipe was adapted from www.seriouseats.com/recipes/2010/01/the-best-chili-recipe... to work in a crock pot.  This recipe was adapted from www.seriouseats.com/recipes/2010/01/the-best-chili-recipe... to work in a crock pot.
Would suggest leaving out the star anise for sure, diced instead of crushed tomatoes to help make the chili less of a paste-soup.  Would suggest leaving out the star anise for sure, diced instead of crushed tomatoes to help make the chili less of a paste-soup.