I created this recipe based on a co-worker's "Red Rocket" Chili, which won best tasting Chili at this year's office Chili Cook-Off. My variant is spicier, darker, and has a smoky taste and a late kick that has earned it "spiciest chili" two years running. The recipe is as close as I'm going to get it to perfect, and can be tweaked (as any good chili recipe) to be milder, sweeter, or if you dare, hotter.
You will need:
The night before you intend to cook the chili:
Rinse the beans and pour into a large pot. Add four pints of Guinness, and cover the pot. Set it aside. In a small jar combine olive oil with: your two hottest peppers, puréed; 1/8 onion, puréed;, 1 clove garlic, finely chopped. Add a dash of cayenne and cumin, and some of your hot sauce if you want. Close the jar and shake well. Refrigerate this mixture.
When you're ready to cook the chili:
At least 6 hours after you poured Guinness on your beans, drain (but do not rinse) the beans. Add three pints of Guinness and bring the beans to a boil. Simmer with the lid tilted (to allow steam to escape) for 1.5 hours. With about 15 minutes to go before the beans are done, pour the oil mixture in a deep cast iron skillet and apply very low heat. Begin finely chopping all of your remaining vegetables except one hot pepper. When the oil starts sizzling, add the ground beef and bring the mixture to medium heat, stirring in vegetables as the beef gets darker.
When the beef is completely browned and the vegetables are starting to brown or go limp, gradually stir in crushed tomatoes and beans, mixing over medium heat. Add cumin until your chili smells like chili. Add brown sugar and honey to taste (sweeter if you plan to serve it sooner, since it will initially have a bitter taste). Heat until the mixture begins to dry out, and add a pint of Guiness. Stir over low to heat, adding spices to taste. Make sure that the mixture simmers long enough to thicken back into chili (let the majority of the Guinness evaporate).
Transfer to a crock pot and let simmer on low heat until ready to serve. Garnish with a hot pepper.
This chili typically hits in two waves: the cayenne and black pepper break through the sweetness and smoky/bitter Guinness taste first, the hot peppers and hot sauce second. For best effect, don't overdo the former, so that the flavor is sweet (or bitter), then tangy, then hot. The escalation effect can make this chili seem stronger than it is.
An alternative to the searing hot version above uses Harp lager, red kidney beans, and a pasilla pepper and two serrano peppers instead of the full complement of four peppers above; the serranos are used in the hot oil mixture, and the pasilla is a milder (but still tasty) medium-hot pepper that gets chopped in during the beef browning stage.