Chop the bacon into 1/2-inch pieces and place in a large heavy-bottomed pot or Dutch oven over medium heat. Cook, stirring occasionally, until the bacon is crispy and has rendered its fat, about 8-10 minutes. The rendered fat will become your cooking medium and add tremendous flavor to the dish. Remove the bacon with a slotted spoon and set aside, leaving the bacon fat in the pot.
While the bacon cooks, finely dice the yellow onion and celery into 1/4-inch pieces. Measure out all dry spices (chili powder, paprika, cumin) and the flour into a small bowl. Open your beer and have the Worcestershire sauce, tomato sauce, water, diced tomatoes, and chili beans ready nearby. I prefer to have everything measured and within reach before the cooking gets intense—it keeps the process smooth and prevents overseasoning.
Increase the heat under the pot to medium-high. Add the ground beef in batches, breaking it up with a wooden spoon as it cooks—avoid stirring constantly, as this allows the meat to brown and develop flavor rather than steam. Once the beef is mostly browned (about 8-10 minutes total), sprinkle with salt and stir in the flour. The flour will help thicken the chili and create a light fond on the bottom of the pot. Cook the flour into the meat for 1-2 minutes, stirring constantly.
Reduce heat to medium and add the diced onion and celery to the beef. Cook for 3-4 minutes, stirring occasionally, until the vegetables begin to soften and release their aromatics. Add the chili powder, paprika, and cumin from your spice mixture, stirring constantly for about 1 minute—this blooming process awakens the spices and prevents them from tasting raw. Pour in the 12 oz stout beer, using a wooden spoon to scrape up any flavorful browned bits stuck to the bottom of the pot. These fond bits are pure flavor and essential to great chili.
Stir in the Worcestershire sauce, tomato sauce, diced tomatoes (with their juices), water, and the two cans of chili beans (drained and rinsed). Add the cooked bacon back into the pot and stir well to combine. I always rinse my canned beans because it removes excess sodium and starch, giving you a cleaner, more balanced chili. Bring the mixture to a gentle simmer over medium heat, then reduce to low.
Let the chili simmer gently on low heat, uncovered or with the lid slightly ajar, for 45-60 minutes. Stir occasionally to prevent sticking on the bottom. The long, slow simmer allows the flavors to deepen and the sauce to thicken naturally as liquid reduces. The chili is done when it has achieved a thick, pourable consistency and the flavors taste well-integrated rather than individual. Taste and adjust seasoning with additional salt, chili powder, or Worcestershire sauce as needed. The chili will thicken slightly more as it cools.