Heat 2 tablespoons vegetable oil in a large heavy-bottomed pot or Dutch oven over medium-high heat until shimmering. Add the diced onion and a pinch of salt; sauté 4–5 minutes until softened and translucent. Add the bell pepper and jalapeño and cook 3 minutes more. Stir in the minced garlic and cook 30 seconds until aromatic.

Brown meats

Push vegetables to the side and add ground beef to the pot. Break it up with a wooden spoon and brown until no longer pink, about 6–8 minutes. Add the sliced smoked sausage and cook 2–3 minutes to render some fat and develop color. If the pot is very dry, add a splash (1–2 tbs) of oil or broth.

Develop flavor

Stir in 2 tablespoons tomato paste and cook 1–2 minutes, stirring constantly, until it darkens slightly. This browns the paste and deepens flavor.

Add liquids & beans

Pour in the canned diced tomatoes (with their juices) and 2 cups beef broth, scraping up any browned bits from the bottom of the pot. Add the drained kidney and pinto beans. Bring the mixture to a gentle simmer.

Spices & Seasoning

Season

Add chili powder, ground cumin, smoked paprika, dried oregano, brown sugar, black pepper, kosher salt, cayenne pepper, and hot sauce to the pot. Stir to combine. Taste and adjust heat or salt as needed.

Simmer

Reduce heat to low and simmer, uncovered, for 30–40 minutes, stirring occasionally, until the chili thickens and flavors meld. If chili becomes too thick, add up to 1/2 cup more beef broth or water to reach desired consistency.

Finishing & Garnish

Finish

Stir in 1 tablespoon apple cider vinegar and 1/4 cup chopped fresh cilantro. Simmer 2 minutes more, then remove from heat. Adjust seasoning with additional salt, pepper, or hot sauce to taste.

Serve

Ladle the cowboy chili into bowls and garnish with shredded cheddar, a dollop of sour cream, and sliced green onions. Sprinkle additional cilantro if desired.