When I first proposed this recipe to my mother, she was more shocked about me choosing to use steak instead of ground beef than the mention of chocolate. She merely batted an eyelash at the latter. While unconventional and strange, both the steak and chocolate make this chili a rich and flavorful stew that convinced my mother that steak has a place in chili, too. Because it reminded us of a Latin-inspired beef stew, we served it over mashed potatoes.
Mix all of the ingredients together in a bowl.
Dredge the meat in the rub well and set aside. Let sit for at least 15 minutes, up to a day.
In a large Dutch oven, heat ½ cup of the vegetable oil over high heat and brown the meat. Remove from the pot and set aside on a plate. Add 1 tablespoon of the vegetable oil to the Dutch oven and heat over medium heat. Add the onions and garlic and cook until translucent, about 2 minutes. Next, add the peppers and cook for 2 more minutes.
Add the cocoa powder and all of the herbs and spices and stir well so that they're well combined and the onions and peppers are coated. Next, add the can of crushed tomatoes, beef stock, and water. Add the meat and all of its juices back to the pot. Stir and bring to a boil.
Once boiling, reduce the heat to a simmer and cover. Cook until the flavors have developed and the meat is tender, about 1 hour. Stir in the beans last and heat through. Skim off the fat before serving.