Pat the beef stew meat dry with paper towels—this is crucial for developing a good brown crust. Season the meat generously with kosher salt and black pepper. While the meat sits, mince your garlic cloves and dice the onion into 1/2-inch pieces. Heat 2 tablespoons of olive oil in a large skillet over medium-high heat until shimmering. Working in batches to avoid crowding, sear the beef for 1-2 minutes per side until deeply browned. Don't worry about cooking it through; you're just building flavor. Transfer the seared meat directly to your crockpot.

In the same skillet you used for the beef (don't clean it—those browned bits add flavor), sauté the diced onion over medium heat for 4-5 minutes until softened and starting to caramelize. Add the minced garlic and cook for 1 minute until fragrant. Now stir in the tomato paste, brown sugar, chili powder, ground cumin, smoked paprika, and dried oregano. Toast this mixture for 1-2 minutes, stirring constantly, so the spices bloom and release their oils—I find this step transforms the flavor from flat to really complex. This is where the chili gets its depth.

Stir the crushed tomatoes and tomato sauce into the spice mixture in your skillet, then let it simmer for 3-5 minutes. This brief simmer helps meld the flavors together and removes any raw tomato taste. Pour this entire mixture over the seared beef in the crockpot. Add the drained and rinsed kidney beans and beef broth, stirring everything together until the meat is submerged and all ingredients are evenly distributed.

Cover your crockpot and cook on high for 3-4 hours or on low for 6-8 hours. The beef should be fork-tender and the flavors well-developed. I prefer the low and slow method because it creates a deeper, more unified flavor, but either works perfectly depending on your schedule.

Once the cooking time is complete, carefully ladle out a spoonful of chili and taste it. Season with additional salt and black pepper as needed—the final seasoning is important for bringing all the flavors to life. Stir well before serving.

Ladle the hot chili into bowls and let diners customize with their favorite toppings. Arrange shredded cheddar cheese, sour cream, sliced jalapeño peppers, green onions, tortilla chips, and cornbread on the side for a build-your-own experience.