Pat the beef stew meat dry with paper towels, then season generously with kosher salt and black pepper on all sides. 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—this creates a flavorful crust that adds richness to the chili. Transfer the seared beef to your crockpot. Without cleaning the pan, add the diced onion to the same skillet and sauté for 4-5 minutes until softened and starting to caramelize. Add the minced garlic and cook for 1 minute until fragrant.

To the sautéed onions and garlic in the skillet, add the chili powder, ground cumin, smoked paprika, and dried oregano. Stir constantly for about 30 seconds to bloom the spices and release their full flavor. Then add the tomato paste and brown sugar, stirring well to combine everything into a paste-like mixture. Pour in the crushed tomatoes and tomato sauce, stirring to deglaze the pan and pick up all the browned bits from searing the beef. Let this simmer for 3-5 minutes to allow the flavors to meld and the tomato sauce to reduce slightly, concentrating its flavor. I like to add tomato paste early because it needs time to cook out its raw taste and develop deeper, more complex flavors.

Pour the tomato and spice mixture from Step 2 over the seared beef in the crockpot. Add the drained and rinsed kidney beans and beef broth, stirring gently to distribute all ingredients evenly. Make sure the beef is mostly submerged in liquid—this ensures even cooking and allows all the flavors to develop together. I find that rinsing the canned beans removes excess sodium and starch, giving the chili a cleaner, brighter finish.

Cover the crockpot and cook on high for 3-4 hours or on low for 6-8 hours. The long, gentle cooking breaks down the tougher cuts of beef stew meat until it becomes tender and absorbs all the chili flavors. Use a skewer or fork to test the meat—it should shred easily when fully cooked. During the last 30 minutes of cooking, taste the chili and adjust the seasoning with additional salt and pepper if needed.

Ladle the hot chili into bowls and set out all the toppings for your guests to customize their own. The cool, creamy contrast of sour cream and the sharp bite of shredded cheddar cheese complement the rich, spiced chili perfectly. Serve alongside tortilla chips for scooping or cornbread for soaking up every last bit of sauce.