In a large skillet, sauté 1/3 of the onion with 2 tablespoons oil over medium heat until softened and browning at the edges, about 8 minutes. Add 1/3 of the steak and garlic to the skillet and cook for 2-3 minutes over medium-high heat (small batches allow the meat to brown better).
Sprinkle 3 tablespoons of the chili seasoning over the meat and continue to cook 1-2 minutes until the spices are fragrant and clinging to the meat (all 4 ounces of chili seasoning should be used). Note: There should also be a nice browned coating on the bottom of the skillet—if it seems like this fond is burning, turn down the heat.
Add 1/3 cup of the red wine to loosen any browned bits and simmer 1 to 2 minutes to evaporate some of the wine. Repeat these steps with each batch and transfer to a large soup pot (at least 8 quarts).
While meat is browning, add the following to the pot: Drained beans, all tomatoes, chilies, and liquid smoke. Continue adding the batches of browned meat and onion to the larger pot when done.
Once all the meat is browned and in the pot with the beans, tomatoes, chiles, and liquid smoke, add enough beef stock to the pot to thin to desired consistency.
Simmer chili on the lowest setting for 1 to 2 hours, stirring occasionally, or place in a slow cooker on low for 4-6 hours.
Final Step: The last 10 minutes of cooking, mix masa harina flour with 1/2 cup of water in a small bowl until smooth. Stir into chili and simmer for 10 minutes; this will thicken the chili and round out the flavors. Salt and pepper, to taste.
Video
Notes
Nutrition values do not include the Homemade Chili Seasoning ingredients.
Recipe Variations:
Make it less spicy by adding more ancho chile powder and less chipotle chile powder
Spice it up with more chipotle chile powder or use chiles like serrano, habanero, or chipotle chiles in adobo
Sub fresh green chiles for canned and cook with onions
Use dried beans instead of canned—one 15 ounce can of beans (drained) is equivalent to 1 1/2 cups of cooked beans. 1/2 cup of dry beans will yield 1 1/2 cups cooked beans. Only add cooked or canned beans to the chili.
If RO*TEL brand tomatoes are not available, add 3/4 cup chopped fresh tomatoes and 2 additional tablespoons of chopped roasted green chiles.
Sub nitro stout for the wine
Make it without alcohol—sub more beef stock mixed with 1 tablespoon apple cider vinegar or cocoa powder for the wine
Like any soup, chili always tastes better the second day, so prepare it in advance and warm-up when ready to eat.